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Chestertown Vacation Rentals with a Pool
Find Luxury Places to Stay Near Chestertown with a Swimming Pool
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About Chestertown Vacation Rentals with Pools on Rent By Owner
Having a pool at your vacation rental will give you a spectacular travel experience for your friends or family. We have more than 14 swimming pool properties that would give you an extra level of fun and excitement, knowing that you can enjoy them anytime, even at night.
Planning for a vacation? Then get a place with access to a private pool, or share a communal indoor/outdoor pool with others in the complex. Looking to rent a vacation home in Chestertown? Rent By Owner helps you find rentals with swimming pools for your next trip. We feature many rental listings with indoor/outdoor or private swimming pools. Are you visiting with family, group, friends, or pets in Chestertown? Find a rental with a private pool or one that is close to a beach, lakeside, or hot tub.
Rent by Owner offers several family-friendly vacation homes with a private indoor or outdoor heated pool that you will enjoy. RBO helps you find the best accommodation for your next trip; whether you are looking for a romantic cottage, luxury villas, resorts, log cabin, or even RV rental.
Frequently Asked Questions About Chestertown Rentals with Pools
There are a lot of options in Chestertown. If you plan on staying in the Chestertown area, consider making a reservation for a few nights at one of these properties as these have been rated the top Vacation Rentals with Pools in Chestertown:
- 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
- Breathtaking waterfront home on the Chester River
- Historic Manor House on Beautiful Eastern Shore Estate
- Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
- A Waterfront Oasis with pier and pool. Spacious 4 bedrooms near Chestertown.
- First Floor Studio Apartment in Historic Chestertown
- Pet-Friendly Home on Chester River w/Dock!
- Comfort Inn & Suites Chestertown
- Comfort Inn & Suites Chestertown
- The Lodge at Great Oak Landing
- Pet-Friendly Home on Chester River w/Dock!
- Thornton
- The Lodge at Great Oak Landing
- First Floor Studio Apartment in Historic Chestertown
See all pet-friendly luxury rentals in Chestertown on Rent By Owner
