
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 Cumberland offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Maryland
- ·
- Cumberland
- 2.34 mi to center
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Private Pool
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Breakfast
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EV Charge Station
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Parking
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Private Pool
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Breakfast
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EV Charge Station
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Parking
- Maryland
- ·
- Cumberland
- 2.35 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
- Cumberland
- ·
- Thayerville
- 0.34 mi to center
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Parking
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Pool
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- Thayerville
- 0.34 mi to center
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Parking
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Pool
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- Thayerville
- 0.34 mi to center
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Parking
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Pool
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- Thayerville
- 0.34 mi to center
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Parking
-
Pool
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- Thayerville
- 0.34 mi to center
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Parking
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Pool
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- Thayerville
- 1.82 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- McHenry
- 2.06 mi to center
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Parking
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Pool
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Air Conditioner
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Internet
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Parking
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Pool
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Air Conditioner
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Internet
- Cumberland
- ·
- Thayerville
- 1.82 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- McHenry
- 1.25 mi to center
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Hot Tub
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Parking
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Pool
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Spa
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Hot Tub
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Parking
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Pool
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Spa
- Cumberland
- ·
- McHenry
- 0.74 mi to center
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Parking
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Skiing
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Air Conditioner
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Internet
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Parking
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Skiing
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Air Conditioner
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Internet
- Cumberland
- ·
- McHenry
- 0.25 mi to center
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Parking
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Skiing
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Sports/Activities
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Security/Safety
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Parking
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Skiing
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Sports/Activities
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Security/Safety
- Cumberland
- ·
- McHenry
- 0.74 mi to center
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Skiing
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Air Conditioner
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Pet Friendly
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Child Friendly
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Skiing
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Air Conditioner
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Pet Friendly
-
Child Friendly
- Cumberland
- ·
- McHenry
- 2.29 mi to center
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Private Pool
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Parking
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Pool
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Skiing
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Private Pool
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Parking
-
Pool
-
Skiing
- Cumberland
- ·
- Thayerville
- 0.85 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- Thayerville
- 1.62 mi to center
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Hot Tub
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Breakfast
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EV Charge Station
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Parking
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Hot Tub
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Breakfast
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EV Charge Station
-
Parking
- Cumberland
- ·
- McHenry
- 1.43 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
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Internet
- Cumberland
- ·
- Thayerville
- 1.23 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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View
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Hot Tub
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Parking
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Balcony/Terrace
-
View
- Cumberland
- ·
- Thayerville
- 0.88 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- Thayerville
- 0.79 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
-
Pool
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Balcony/Terrace
- Cumberland
- ·
- Accident
- 2.95 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
- Cumberland
- ·
- Friendsville
- 6.51 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
- Maryland
- ·
- Cumberland
- 3.12 mi to center
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Parking
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Balcony/Terrace
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View
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Air Conditioner
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Parking
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Balcony/Terrace
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View
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Air Conditioner
- Cumberland
- ·
- Friendsville
- 1.76 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
- Cumberland
- ·
- Accident
- 1.80 mi to center
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Pet Friendly
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Child Friendly
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Pet Friendly
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Child Friendly
- Cumberland
- ·
- Swanton
- 5.29 mi to center
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Air Conditioner
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Pet Friendly
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Child Friendly
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Air Conditioner
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Pet Friendly
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Child Friendly
- Cumberland
- ·
- Little Orleans
- 2.42 mi to center
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Pet Friendly
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Child Friendly
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Pet Friendly
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Child Friendly
- Cumberland
- ·
- Swanton
- 5.29 mi to center
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Pet Friendly
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Child Friendly
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Pet Friendly
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Child Friendly
- Cumberland
- ·
- Swanton
- 5.29 mi to center
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Pet Friendly
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Child Friendly
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Pet Friendly
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Child Friendly
- Cumberland
- ·
- Swanton
- 5.29 mi to center
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Pet Friendly
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Child Friendly
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Pet Friendly
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Child Friendly
- Cumberland
- ·
- Oakland
- 9.54 mi to center
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Parking
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Skiing
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Air Conditioner
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Internet
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Parking
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Skiing
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Air Conditioner
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Internet
- Cumberland
- ·
- McHenry
- 2.30 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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View
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Hot Tub
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Parking
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Balcony/Terrace
-
View
- Cumberland
- ·
- Grantsville
- 2.09 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
- Cumberland
- ·
- Oakland
- 8.55 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
-
Air Conditioner
- Cumberland
- ·
- Thayerville
- 2.06 mi to center
-
Hot Tub
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Parking
-
Pool
-
Balcony/Terrace
-
Hot Tub
-
Parking
-
Pool
-
Balcony/Terrace
- Cumberland
- ·
- Thayerville
- 0.69 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
-
Air Conditioner
- Cumberland
- ·
- Grantsville
- 0.81 mi to center
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
-
Kitchen
- Cumberland
- ·
- Grantsville
- 0.78 mi to center
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Air Conditioner
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Internet
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Child Friendly
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Bedding/Linens
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Air Conditioner
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Internet
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Child Friendly
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Bedding/Linens
- Cumberland
- ·
- North Glade Hills
- 0.49 mi to center
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Internet
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Child Friendly
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Security/Safety
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Internet
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Child Friendly
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Security/Safety
- Cumberland
- ·
- McHenry
- 2.94 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Air Conditioner
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Hot Tub
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Parking
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Balcony/Terrace
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Air Conditioner
- Cumberland
- ·
- North Glade Hills
- 0.49 mi to center
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Internet
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Child Friendly
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Security/Safety
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Internet
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Child Friendly
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Security/Safety
- Cumberland
- ·
- Waterfront Greens
- 0.20 mi to center
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Parking
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Internet
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Pet Friendly
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Child Friendly
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Parking
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Internet
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Pet Friendly
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Child Friendly
- Cumberland
- ·
- Oakland
- 4.81 mi to center
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Parking
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Balcony/Terrace
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Air Conditioner
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Pet Friendly
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Parking
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Balcony/Terrace
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Air Conditioner
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Pet Friendly
Find the Perfect Resort Vacation in the Cumberland
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 Cumberland
What are the Top Resort Locations Across the Cumberland?
Discover resorts in the most sought-after travel destinations nationwide:
Garrett County
Garrett County VACATION RENTALSMcHenry
McHenry VACATION RENTALSOakland
Oakland VACATION RENTALSThayerville
Thayerville VACATION RENTALSSwanton
Swanton VACATION RENTALSMountain Lake Park
Mountain Lake Park VACATION RENTALSWaterfront Greens
Waterfront Greens VACATION RENTALSAllegany County
Allegany County VACATION RENTALSMountainside
Mountainside VACATION RENTALSBlakeslee
Blakeslee VACATION RENTALSDeep Creek Lake
Deep Creek Lake VACATION RENTALSNorth Glade Hills
North Glade Hills VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the Cumberland. 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 Cumberland
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the Cumberland, 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 Cumberland? 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.
- Cumberland
- ·
- McHenry
- 2.94 mi to center
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Hot Tub
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Cumberland
- ·
- Waterfront Greens
- 0.20 mi to center
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Parking
-
Internet
-
Pet Friendly
-
Child Friendly
-
Parking
-
Internet
-
Pet Friendly
-
Child Friendly
- Cumberland
- ·
- North Glade Hills
- 0.49 mi to center
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Internet
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Child Friendly
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Security/Safety
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Internet
-
Child Friendly
-
Security/Safety
- Cumberland
- ·
- North Glade Hills
- 0.49 mi to center
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Internet
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Child Friendly
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Security/Safety
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Internet
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Child Friendly
-
Security/Safety
Resorts Vacations FAQs
What are the top vacation rentals in Cumberland?
There are a lot of options in Cumberland. If you plan on staying in the Cumberland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cumberland:
- The Lodge at Wisp Resort
- The Iconic Red Roof Lakefront Estate of Deep Creek Lake - 8BR Sleeps 20
- Playin Hooky by Railey Vacations
- Beary Fine Resort by Railey Vacations
- Bear Ridge Resort by Railey Vacations
- Aria Resort by Railey Vacations
- Private Rm 1, Handicap Accessible, 10 quiet acres
- Private Rm 1, Handicap Accessible, 10 quiet acres
How many vacation rentals have private pools in Cumberland?
There are 185 vacation rentals with private pools near Cumberland. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Cumberland are best for families?
If you are looking for a family-friendly vacation home in Cumberland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cumberland:
How many vacation rentals are available in Cumberland?
Currently, the total number of properties listed in 2026 is over 8 in the Cumberland area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Cumberland.
More Resorts Vacations to Explore
- Cumberland
- ·
- Waterfront Greens
- 0.20 mi to center
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Parking
-
Internet
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Pet Friendly
-
Child Friendly
-
Parking
-
Internet
-
Pet Friendly
-
Child Friendly
- Cumberland
- ·
- McHenry
- 2.94 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Air Conditioner
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Cumberland
- ·
- North Glade Hills
- 0.49 mi to center
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Internet
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Child Friendly
-
Security/Safety
-
Internet
-
Child Friendly
-
Security/Safety