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

Home in Chestertown
4.92 out of 5 average rating, 168 reviewsHistoric Chestertown
Superhost

Home in Chestertown
4.76 out of 5 average rating, 17 reviewsLangford Creek | Waterfront w/ HOT TUB + Fire Pit!
Top guest favourite

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

Home in Rock Hall
4.92 out of 5 average rating, 48 reviewsHistoric Cottage | 1min DT | Views | W/D | Parking
Guest favourite

Home in Rock Hall
4.89 out of 5 average rating, 37 reviewsThe Blue Jimmy
Guest favourite

Home in Chestertown
4.97 out of 5 average rating, 98 reviewsThe Patriot House-Chestertown, MD
Guest favourite

Home in Chestertown
5 out of 5 average rating, 25 reviewsHistoric house on High Street, Chestertown, MD
Top guest favourite

Home in Chestertown
5 out of 5 average rating, 53 reviewsGoose Haven, new waterfront house on Fairlee Creek
Quick stats about vacation rentals in Chestertown
Total rentals
40 properties
Nightly prices starting at
$124 CAD 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
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- Fortescue Beach
- Betterton Beach
- Oriole Park at Camden Yards
- Longwood Gardens
- M&T Bank Stadium
- Hampden
- Sandy Point State Park
- Patterson Park
- Big Stone Beach
- Six Flags America
- Maryland Renaissance Festival
- Crystal Beach Manor, Earleville, MD
- Caves Valley Golf Club
- Killens Pond State Park
- Bulle Rock Golf Course
- DuPont Country Club
- Quiet Waters Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- White Clay Creek Country Club
- Chesapeake Beach Water Park
- Lums Pond State Park
- Susquehanna State Park
- Gerry Boyle Park
- Breezy Point Beach & Campground