
Holiday rentals in Chestertown
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Top-rated holiday rentals in Chestertown
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Chestertown holiday rentals
Other great holiday rentals in Chestertown
Top guest favourite

Home in Chestertown
5 out of 5 average rating, 26 reviewsChestertown Watson Family Farm

Home in Chestertown
4.92 out of 5 average rating, 168 reviewsHistoric Chestertown
Top guest favourite

Home in Chestertown
4.99 out of 5 average rating, 108 reviewsEntire River Front Home - 4 Bedrooms 4.5 Baths
Guest favourite

Home in Rock Hall
4.89 out of 5 average rating, 36 reviewsThe Blue Jimmy
Guest favourite

Townhouse in Chestertown
4.8 out of 5 average rating, 15 reviewsThe Retreat in Historic Downtown Chestertown
Superhost

Home in Rock Hall
4.86 out of 5 average rating, 7 reviewsChesapeake Bay Retreat W/Breathtaking Views
Top guest favourite

Home in Chestertown
5 out of 5 average rating, 43 reviewsIn Town Chestertown Rancher (1 Block to College)
Guest favourite

Home in Chestertown
5 out of 5 average rating, 25 reviewsHistoric house on High Street, Chestertown, MD
Quick stats about holiday rentals in Chestertown
Total rentals
40 properties
Nightly prices starting at
₹7,723 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Washington Holiday rentals
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- Fortescue Beach
- Betterton Beach
- Longwood Gardens
- Oriole Park at Camden Yards
- Hampden
- M&T Bank Stadium
- Sandy Point State Park
- Patterson Park
- Maryland Renaissance Festival
- Crystal Beach Manor, Earleville, MD
- Six Flags America
- Caves Valley Golf Club
- Quiet Waters Park
- Killens Pond State Park
- Heritage Shores
- Bulle Rock Golf Course
- DuPont Country Club
- Lums Pond State Park
- Gerry Boyle Park
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Susquehanna State Park
- White Clay Creek Country Club
- Bayfront Beach