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House vacation rentals in Chestertown
Find and book unique houses on Airbnb
Top-rated house rentals in Chestertown
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chestertown house rentals
House rentals with a pool
![](https://a0.muscache.com/im/pictures/airflow/Hosting-15205495/original/3e4a7777-2362-471d-b68f-9df1afe2d5f9.jpg?im_w=720)
Home in Saint Michaels
4.97 out of 5 average rating, 244 reviewsMiles Aweigh
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Home in Severn
4.83 out of 5 average rating, 116 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
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Home in Queenstown
4.82 out of 5 average rating, 148 reviewsBay Breeze Retreat
![](https://a0.muscache.com/im/pictures/miso/Hosting-52172926/original/b5666f0a-00d3-44e5-b9d3-a3dd97769178.jpeg?im_w=720)
Home in Edgewater
4.94 out of 5 average rating, 126 reviewsHouse in Edgewater Maryland
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Home in Harwood
4.94 out of 5 average rating, 122 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
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Home in Shady Side
4.88 out of 5 average rating, 177 reviewsCattail Landing- Photographer's Waterfront Retreat
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Home in Millington
4.86 out of 5 average rating, 42 reviewsThe Peaceful Getaway (with private pool & hot tub)
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Home in Rock Hall
4.93 out of 5 average rating, 30 reviewsRockfish Keeper
Weekly house rentals
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Home in Chestertown
5 out of 5 average rating, 26 reviewsIn Town Chestertown Rancher (1 Block to College)
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Home in Chestertown
4.85 out of 5 average rating, 41 reviewsHarbor View Haven | Waterfront w/ HOT TUB + Dock!
![](https://a0.muscache.com/im/pictures/miso/Hosting-725294314624610657/original/3aaaec1c-ba93-4817-b87e-888eca0818bb.jpeg?im_w=720)
Home in Chestertown
5 out of 5 average rating, 28 reviewsMagnolia House: walk to shops, restaurants, river
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Home in Rock Hall
4.97 out of 5 average rating, 33 reviewsChesapeake Bay Retreat w/ Views!
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Home in Chestertown
5 out of 5 average rating, 22 reviewsDown by the River
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Home in Chestertown
4.96 out of 5 average rating, 26 reviewsRiver Cottage, Chestertown
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Home in Greensboro
4.97 out of 5 average rating, 58 reviewsCozy 2 bedroom home on wooded private lane
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Home in Chestertown
4.91 out of 5 average rating, 46 reviewsWknd Beach Getaway w/ Kayak, Deck, Grill & Firepit
Private house rentals
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Home in Millington
4.95 out of 5 average rating, 20 reviewsLark's Nest on the Chester River
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Home in Betterton
5 out of 5 average rating, 27 reviewsRuby's Sea Glass Cottage near Betterton Beach
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Home in Rock Hall
5 out of 5 average rating, 78 reviewsCozy 1920's Bungalow Near Water/Local Attractions
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Home in Chester
5 out of 5 average rating, 14 reviewsThe Fitz Inn
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Home in Rock Hall
4.97 out of 5 average rating, 29 reviewsEastern Shore Escape in the Heart of Rock Hall
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Home in Bel Air
4.82 out of 5 average rating, 28 reviewsCozy Private Entire Ground Unit in Bel Air
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Home in Pasadena
5 out of 5 average rating, 25 reviewsWaterfront CHeerful 2 with Private home
![](https://a0.muscache.com/im/pictures/miso/Hosting-1154274044511200673/original/44d11f19-2554-43a7-9a96-9037aa559aea.jpeg?im_w=720)
Home in North East
5 out of 5 average rating, 7 reviewsThe Riverside Oasis
Quick stats about house rentals in Chestertown
Total rentals
20 properties
Total number of reviews
1.3K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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