House holiday rentals in Chestertown
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Top-rated house rentals in Chestertown
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Chestertown
House rentals with a pool
Home in Queenstown
4.81 out of 5 average rating, 142 reviewsBay Breeze Retreat
Home in Edgewater
4.95 out of 5 average rating, 123 reviewsHouse in Edgewater Maryland
Home in Harwood
4.94 out of 5 average rating, 119 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Home in Shady Side
4.88 out of 5 average rating, 175 reviewsCattail Landing- Photographer's Waterfront Retreat
Home in Millington
4.86 out of 5 average rating, 36 reviewsThe Peaceful Getaway (with private pool & hot tub)
Home in Church Hill
4.94 out of 5 average rating, 48 reviewsPrivate Peaceful Waterfront House w/ Pool, Hot Tub
Home in Rock Hall
4.92 out of 5 average rating, 26 reviewsRockfish Keeper
Home in Queen Anne
4.97 out of 5 average rating, 30 reviewsFarmhouse w/hot tub, close to Tuckohoe State Park
Weekly house rentals
Home in Chestertown
4.88 out of 5 average rating, 32 reviewsBeautifully remodeled home in Historic Chestertown
Home in Chestertown
4.96 out of 5 average rating, 78 reviewsCozy 3-bedroom home w/ screened in porch & firepit
Home in Chestertown
5.0 out of 5 average rating, 41 reviewsWaterfront house with private dock & kayaks!
Home in Chestertown
5.0 out of 5 average rating, 26 reviews125 High - Luxury Historical Brick Victorian
Home in Chestertown
5.0 out of 5 average rating, 26 reviewsMagnolia House: walk to shops, restaurants, river
Home in Chestertown
5.0 out of 5 average rating, 17 reviewsNEW Chestertown Retreat
Home in Chestertown
5.0 out of 5 average rating, 54 reviewsLovely Home in Chestertown With Free EV Charging
Home in Chestertown
5.0 out of 5 average rating, 78 reviewsRiver front cottage with private dock & water fun
Private house rentals
Home in Chestertown
5.0 out of 5 average rating, 18 reviewsDown by the River
Home in Rock Hall
4.96 out of 5 average rating, 24 reviewsChesapeake Bay Retreat w/ Views!
Home in Chestertown
4.96 out of 5 average rating, 25 reviewsRiver Cottage, Chestertown
Home in Abingdon
4.96 out of 5 average rating, 70 reviewsAbingdonBB
Home in Chestertown
4.93 out of 5 average rating, 42 reviewsBeach Access, Dive Bar, Dock w/ Grill & Firepit
Home in Millington
4.93 out of 5 average rating, 15 reviewsLark's Nest on the Chester River
Home in Betterton
5.0 out of 5 average rating, 20 reviewsRuby's Sea Glass Cottage near Betterton Beach
Home in Rock Hall
4.97 out of 5 average rating, 33 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Quick stats about house rentals in Chestertown
Total rentals
20 properties
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.3K reviews
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