
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 Chester offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Missouri
- ·
- Perryville
- 1.33 mi to center
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Private Pool
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Parking
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Pool
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Spa
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Private Pool
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Parking
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Pool
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Spa
- Missouri
- ·
- Perryville
- 1.39 mi to center
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Breakfast
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Parking
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Pool
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Kitchen
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Breakfast
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Parking
-
Pool
-
Kitchen
- Missouri
- ·
- Perryville
- 0.93 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
- Missouri
- ·
- Perryville
- 0.66 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
- Missouri
- ·
- Perryville
- 0.87 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
- Missouri
- ·
- Perryville
- 1.01 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
- Missouri
- ·
- Perryville
- 0.60 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
- Perryville
- ·
- Ste Genevieve
- 4.02 mi to center
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Parking
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Balcony/Terrace
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Kitchen
-
Air Conditioner
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Missouri
- ·
- Perryville
- 4.56 mi to center
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Parking
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Balcony/Terrace
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Internet
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Security/Safety
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Parking
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Balcony/Terrace
-
Internet
-
Security/Safety
- Chester
- ·
- Prairie du Rocher
- 0.14 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
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.68 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
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.99 mi to center
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Parking
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Balcony/Terrace
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Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 5.30 mi to center
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Private Pool
-
Hot Tub
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Parking
-
Pool
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Private Pool
-
Hot Tub
-
Parking
-
Pool
- Perryville
- ·
- Ste Genevieve
- 8.69 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Perryville
- ·
- Ste Genevieve
- 4.97 mi to center
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Private Pool
-
Hot Tub
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Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Missouri
- ·
- Perryville
- 8.64 mi to center
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Hot Tub
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Kitchen
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Air Conditioner
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Laundry
-
Hot Tub
-
Kitchen
-
Air Conditioner
-
Laundry
- Missouri
- ·
- Perryville
- 6.82 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Internet
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Internet
- Missouri
- ·
- Perryville
- 8.66 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Missouri
- ·
- Perryville
- 6.82 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Kitchen
-
Air Conditioner
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Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Chester
- ·
- Saint Mary
- 3.74 mi to center
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Private Pool
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Hot Tub
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Parking
-
Pool
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Private Pool
-
Hot Tub
-
Parking
-
Pool
- Perryville
- ·
- Ste Genevieve
- 4.02 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
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Missouri
- ·
- Perryville
- 4.56 mi to center
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Parking
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Balcony/Terrace
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Internet
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Security/Safety
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Parking
-
Balcony/Terrace
-
Internet
-
Security/Safety
- Chester
- ·
- Prairie du Rocher
- 0.14 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
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.68 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
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.99 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
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 5.30 mi to center
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Perryville
- ·
- Ste Genevieve
- 8.69 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
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Perryville
- ·
- Ste Genevieve
- 4.97 mi to center
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Perryville
- ·
- Ste Genevieve
- 8.85 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
- Perryville
- ·
- Ste Genevieve
- 8.78 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
- Perryville
- ·
- Ste Genevieve
- 8.78 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
- Missouri
- ·
- Lake Forest Estates
- 9.2 mi to center
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Air Conditioner
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Internet
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Child Friendly
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Laundry
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Air Conditioner
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Internet
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Child Friendly
-
Laundry
-
Kitchen
-
Child Friendly
-
Security/Safety
-
Kitchen
-
Child Friendly
-
Security/Safety
-
Child Friendly
-
Security/Safety
-
Child Friendly
-
Security/Safety
- Perryville
- ·
- Ste Genevieve
- 4.02 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
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Missouri
- ·
- Perryville
- 4.56 mi to center
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Parking
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Balcony/Terrace
-
Internet
-
Security/Safety
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Parking
-
Balcony/Terrace
-
Internet
-
Security/Safety
- Chester
- ·
- Prairie du Rocher
- 0.14 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
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.68 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.99 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 5.30 mi to center
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Perryville
- ·
- Ste Genevieve
- 8.69 mi to center
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Perryville
- ·
- Ste Genevieve
- 4.97 mi to center
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Chester
- ·
- Saint Mary
- 10.91 mi to center
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Private Pool
-
Pool
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Balcony/Terrace
-
Kitchen
-
Private Pool
-
Pool
-
Balcony/Terrace
-
Kitchen
- Missouri
- ·
- Perryville
- 1.47 mi to center
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Parking
-
Pool
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Balcony/Terrace
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Internet
-
Parking
-
Pool
-
Balcony/Terrace
-
Internet
Find the Perfect Resort Vacation in the Chester
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 Chester
What are the Top Resort Locations Across the Chester?
Discover resorts in the most sought-after travel destinations nationwide:
Memorial Hospital
Memorial Hospital VACATION RENTALSElzie C. Segar Memorial Park
Elzie C. Segar Memorial Park VACATION RENTALSPopeye Museum
Popeye Museum VACATION RENTALSChester Skating Rink
Chester Skating Rink VACATION RENTALSKaskaskia Bell
Kaskaskia Bell VACATION RENTALSMary's River Covered Bridge
Mary's River Covered Bridge VACATION RENTALSSaint Mary
Saint Mary VACATION RENTALSBremen
Bremen VACATION RENTALSPrairie du Rocher
Prairie du Rocher VACATION RENTALSSparta
Sparta VACATION RENTALSMisselhorn Art Gallery
Misselhorn Art Gallery VACATION RENTALSBaldwin
Baldwin VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the Chester. 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 Chester
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the Chester, 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 Chester? 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.
- Perryville
- ·
- Ste Genevieve
- 4.02 mi to center
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Parking
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Balcony/Terrace
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Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.68 mi to center
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Parking
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Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 5.30 mi to center
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
- Perryville
- ·
- Ste Genevieve
- 8.69 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Perryville
- ·
- Ste Genevieve
- 4.97 mi to center
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Private Pool
-
Hot Tub
-
Parking
-
Pool
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.85 mi to center
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.78 mi to center
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Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.57 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
- Chester
- ·
- Prairie du Rocher
- 0.14 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
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Air Conditioner
- Perryville
- ·
- Ste Genevieve
- 8.92 mi to center
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Internet
- Chester
- ·
- Saint Mary
- 10.90 mi to center
-
Private Pool
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Parking
-
Pool
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Balcony/Terrace
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Private Pool
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Parking
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Pool
-
Balcony/Terrace
Resorts Vacations FAQs
Which vacation homes in Chester are best for families?
If you are looking for a family-friendly vacation home in Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chester:
How many vacation rentals are available in Chester?
Currently, the total number of properties listed in 2026 is over 110 in the Chester area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chester.
More Resorts Vacations to Explore
-
Hot Tub
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Parking
-
Pool
-
Air Conditioner
-
Hot Tub
-
Parking
-
Pool
-
Air Conditioner
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Pet Friendly
- Missouri
- ·
- Perryville
- 1.39 mi to center
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Parking
-
Pool
-
Air Conditioner
-
Internet
-
Parking
-
Pool
-
Air Conditioner
-
Internet
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Air Conditioner
- Missouri
- ·
- Perryville
- 1.33 mi to center
-
Private Pool
-
Parking
-
Pool
-
Spa
-
Private Pool
-
Parking
-
Pool
-
Spa
- Missouri
- ·
- Perryville
- 1.38 mi to center
-
Hot Tub
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Breakfast
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Parking
-
Pool
-
Hot Tub
-
Breakfast
-
Parking
-
Pool
- Missouri
- ·
- Perryville
- 1.41 mi to center
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Breakfast
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Parking
-
Pool
-
Balcony/Terrace
-
Breakfast
-
Parking
-
Pool
-
Balcony/Terrace
-
Breakfast
-
Parking
-
Pool
-
Kitchen
-
Breakfast
-
Parking
-
Pool
-
Kitchen
- Missouri
- ·
- Perryville
- 1.33 mi to center
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Breakfast
-
Parking
-
Pool
-
Kitchen
-
Breakfast
-
Parking
-
Pool
-
Kitchen
- Missouri
- ·
- Perryville
- 1.38 mi to center
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Hot Tub
-
Parking
-
Pool
-
Air Conditioner
-
Hot Tub
-
Parking
-
Pool
-
Air Conditioner
- Missouri
- ·
- Perryville
- 1.47 mi to center
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Parking
-
Pool
-
Balcony/Terrace
-
Internet
-
Parking
-
Pool
-
Balcony/Terrace
-
Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet