
Discover the Best Resort Vacations
Explore the top resorts, from luxury beachfront escapes to family-friendly all-inclusive resorts and relaxing spa retreats. Whether you’re planning a weekend getaway or an extended vacation, the Gloucester offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Massachusetts
- ·
- Gloucester
- 1.59 mi to center
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Breakfast
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Parking
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Pool
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Balcony/Terrace
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Breakfast
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Parking
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Pool
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 1.58 mi to center
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 1.42 mi to center
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Breakfast
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Parking
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Pool
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Balcony/Terrace
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Breakfast
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Parking
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Pool
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.40 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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View
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Breakfast
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Parking
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 1.49 mi to center
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Breakfast
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Parking
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Pool
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Balcony/Terrace
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Breakfast
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Parking
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Pool
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.05 mi to center
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Parking
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Air Conditioner
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Internet
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Child Friendly
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Parking
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Air Conditioner
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Internet
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Child Friendly
- Massachusetts
- ·
- Gloucester
- 1.58 mi to center
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.99 mi to center
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Parking
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Ocean View
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View
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Kitchen
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Parking
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Ocean View
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View
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Kitchen
- Massachusetts
- ·
- Gloucester
- 4.20 mi to center
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Oceanfront
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Parking
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Spa
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Ocean View
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Oceanfront
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Parking
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Spa
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Ocean View
- Massachusetts
- ·
- Gloucester
- 0.25 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.41 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.54 mi to center
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Hot Tub
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Parking
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Ocean View
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Balcony/Terrace
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Hot Tub
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Parking
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Ocean View
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.52 mi to center
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Parking
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Air Conditioner
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Child Friendly
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Parking
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Air Conditioner
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Child Friendly
- Massachusetts
- ·
- Gloucester
- 0.40 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Air Conditioner
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Breakfast
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Parking
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Balcony/Terrace
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Air Conditioner
- Massachusetts
- ·
- Gloucester
- 4.55 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
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Kitchen
- Massachusetts
- ·
- Gloucester
- 1.83 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
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Kitchen
- Massachusetts
- ·
- Gloucester
- 0.85 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 4.12 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 3.08 mi to center
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Oceanfront
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Hot Tub
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Parking
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Ocean View
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Oceanfront
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Hot Tub
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Parking
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Ocean View
- Massachusetts
- ·
- Gloucester
- 0.54 mi to center
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Hot Tub
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Parking
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Ocean View
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Balcony/Terrace
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Hot Tub
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Parking
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Ocean View
-
Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.52 mi to center
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Parking
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Air Conditioner
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Child Friendly
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Parking
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Air Conditioner
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Child Friendly
- Massachusetts
- ·
- Gloucester
- 0.40 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Air Conditioner
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Breakfast
-
Parking
-
Balcony/Terrace
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Air Conditioner
- Massachusetts
- ·
- Gloucester
- 4.55 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 1.83 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 0.85 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 4.12 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 3.08 mi to center
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Oceanfront
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Hot Tub
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Parking
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Ocean View
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Oceanfront
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Hot Tub
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Parking
-
Ocean View
- Massachusetts
- ·
- Gloucester
- 4.12 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 1.29 mi to center
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Parking
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View
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Internet
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Pet Friendly
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Parking
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View
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Internet
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Pet Friendly
- Massachusetts
- ·
- Gloucester
- 1.87 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 1.22 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 0.94 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
- Massachusetts
- ·
- Gloucester
- 1.29 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 2.07 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 4.14 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 0.54 mi to center
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Hot Tub
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Parking
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Ocean View
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Balcony/Terrace
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Hot Tub
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Parking
-
Ocean View
-
Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.52 mi to center
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Parking
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Air Conditioner
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Child Friendly
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Parking
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Air Conditioner
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Child Friendly
- Massachusetts
- ·
- Gloucester
- 0.40 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Air Conditioner
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Breakfast
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Parking
-
Balcony/Terrace
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Air Conditioner
- Massachusetts
- ·
- Gloucester
- 4.55 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
-
View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 1.83 mi to center
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Parking
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Balcony/Terrace
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View
-
Kitchen
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Parking
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Balcony/Terrace
-
View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 0.85 mi to center
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Parking
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Ocean View
-
Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 4.12 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
-
Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 3.08 mi to center
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Oceanfront
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Hot Tub
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Parking
-
Ocean View
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
- Massachusetts
- ·
- Gloucester
- 0.54 mi to center
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Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.52 mi to center
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Parking
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Air Conditioner
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Child Friendly
-
Parking
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Air Conditioner
-
Child Friendly
- Massachusetts
- ·
- Gloucester
- 0.40 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Air Conditioner
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Breakfast
-
Parking
-
Balcony/Terrace
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Air Conditioner
- Massachusetts
- ·
- Gloucester
- 4.55 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
-
View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 1.83 mi to center
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Parking
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Balcony/Terrace
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View
-
Kitchen
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Parking
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Balcony/Terrace
-
View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 0.85 mi to center
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Parking
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Ocean View
-
Balcony/Terrace
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View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 4.12 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
-
Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 3.08 mi to center
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Oceanfront
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Hot Tub
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Parking
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Ocean View
-
Oceanfront
-
Hot Tub
-
Parking
-
Ocean View
Find the Perfect Resort Vacation in the Gloucester
What makes our resorts stand out?
Verified Properties
Every vacation home shown on Resort Vacation comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Popular Resort Destinations in the Gloucester
What are the Top Resort Locations Across the Gloucester?
Discover resorts in the most sought-after travel destinations nationwide:
Dogtown
Dogtown VACATION RENTALSGood Harbor Beach
Good Harbor Beach VACATION RENTALSAnnisquam
Annisquam VACATION RENTALSPlum Cove Beach
Plum Cove Beach VACATION RENTALSNortheast Hospital Corporation - Addison Gilbert Campus
Northeast Hospital Corporation - Addison Gilbert Campus VACATION RENTALSCape Ann Museum
Cape Ann Museum VACATION RENTALSCape Ann Historical Museum
Cape Ann Historical Museum VACATION RENTALSSargent House Museum
Sargent House Museum VACATION RENTALSSchooner Adventure
Schooner Adventure VACATION RENTALSGloucester Unitarian Universalist Church
Gloucester Unitarian Universalist Church VACATION RENTALSLucky 7 Arcade
Lucky 7 Arcade VACATION RENTALSMagnolia
Magnolia VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the Gloucester. Once you find the perfect resort, you’ll be seamlessly guided to our partner’s secure booking platform to complete your reservation with confidence.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Common Resort Vacation Amenities in the Gloucester
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the Gloucester, designed for comfort, convenience, and memorable experiences.
Indoor Amenities
Spacious guest rooms and suites
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Places to Stay with Resorts Vacations
Looking for the perfect resort vacation in the Gloucester? Discover a curated collection of resort stays offering comfort, convenience, and unforgettable experiences in top destinations nationwide. Whether you’re searching for a beachfront resort, a family-friendly escape, or a luxury retreat, Resorts Vacations makes it easy to explore and compare verified resort options for your next getaway.
- Massachusetts
- ·
- Gloucester
- 1.87 mi to center
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Parking
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Ocean View
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Balcony/Terrace
-
View
-
Parking
-
Ocean View
-
Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 0.54 mi to center
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Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
-
Hot Tub
-
Parking
-
Ocean View
-
Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 0.81 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
-
Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 4.55 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 2.08 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 2.38 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 3.17 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
-
View
- Gloucester
- ·
- Magnolia
- 0.21 mi to center
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
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Oceanfront
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Parking
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Ocean View
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 1.17 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
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View
- Massachusetts
- ·
- Gloucester
- 2.99 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 0.41 mi to center
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Ocean View
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Balcony/Terrace
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View
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Kitchen
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Ocean View
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Balcony/Terrace
-
View
-
Kitchen
- Massachusetts
- ·
- Gloucester
- 2.04 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
-
Kitchen
Resorts Vacations FAQs
How many vacation rentals have private pools in Gloucester?
There are 2 vacation rentals with private pools near Gloucester. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Gloucester are best for families?
If you are looking for a family-friendly vacation home in Gloucester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Gloucester:
How many vacation rentals are available in Gloucester?
Currently, the total number of properties listed in 2026 is over 424 in the Gloucester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Gloucester.
More Resorts Vacations to Explore
- Massachusetts
- ·
- Gloucester
- 0.64 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
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Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 0.27 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
-
Kitchen
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Air Conditioner
- Massachusetts
- ·
- Gloucester
- 0.49 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Internet
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Parking
-
Balcony/Terrace
-
Kitchen
-
Internet
- Massachusetts
- ·
- Gloucester
- 1.22 mi to center
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Parking
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Balcony/Terrace
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Kitchen
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Internet
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Parking
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Balcony/Terrace
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Kitchen
-
Internet
- Massachusetts
- ·
- Gloucester
- 0.54 mi to center
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Parking
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Ocean View
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Balcony/Terrace
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View
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Parking
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Ocean View
-
Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 2.42 mi to center
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Private Beach
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Oceanfront
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Parking
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Ocean View
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Private Beach
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Oceanfront
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Parking
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Ocean View
- Massachusetts
- ·
- Gloucester
- 0.48 mi to center
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Parking
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Internet
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Child Friendly
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Sports/Activities
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Parking
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Internet
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Child Friendly
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Sports/Activities
- Massachusetts
- ·
- Gloucester
- 1.48 mi to center
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Parking
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Pool
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Balcony/Terrace
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View
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Parking
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Pool
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Balcony/Terrace
-
View
- Massachusetts
- ·
- Gloucester
- 1.60 mi to center
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Parking
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Air Conditioner
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Internet
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Pet Friendly
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Parking
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Air Conditioner
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Internet
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Pet Friendly
- Massachusetts
- ·
- Gloucester
- 1.58 mi to center
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 1.49 mi to center
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Breakfast
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Parking
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Pool
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Balcony/Terrace
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Breakfast
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Parking
-
Pool
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Balcony/Terrace
- Massachusetts
- ·
- Gloucester
- 1.82 mi to center
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Parking
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Pool
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View
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Air Conditioner
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Parking
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Pool
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View
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Air Conditioner