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Search results; 374 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 private bathroom
22–27 Jul
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4.98 out of 5 average rating, 197 reviews
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Flat in Chestertown
Secluded and romantic getaway in Chestertown
4.97 out of 5 average rating, 282 reviews, 2 beds, 1 bathroom
5–10 Jul
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Home in Chestertown
Heart of Historic Chestertown - Church Alley
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
6–11 Jul
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Home in Chestertown
Gorgeous home in town center & 4 blocks from WAC
5.0 out of 5 average rating, 241 reviews, 5 bedrooms, 6 beds, 4 bathrooms
5–10 Jul
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Home in Chestertown
Charming Haven on High
4.96 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
4.98 out of 5 average rating, 180 reviews, 3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
5.0 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
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Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
5.0 out of 5 average rating, 146 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Superhost
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 4 beds, 1 bathroom
5–10 Jul
Guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
4.91 out of 5 average rating, 35 reviews, 3 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
Guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4.93 out of 5 average rating, 85 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
5–10 Jul
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Home in Betterton
Ruby's Sea Glass Cottage near Betterton Beach
4.98 out of 5 average rating, 64 reviews, 3 bedrooms, 5 beds, 1 bathroom
5–10 Jul
Home in Chestertown
Riverside at Pear Tree Point | Waterfront Escape
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
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Home in Chestertown
Classic Victorian in Chestertown
4.96 out of 5 average rating, 137 reviews, 4 bedrooms, 8 beds, 2.5 bathrooms
10–15 Jul
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
4.95 out of 5 average rating, 108 reviews, 3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
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Home in Chestertown
Waterfront Home with Private Dock | Peaceful Stay
5.0 out of 5 average rating, 86 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
4.99 out of 5 average rating, 133 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
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Home in Chestertown
High Tide & Hound
4.98 out of 5 average rating, 82 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
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Home in Worton
Cozy Cape Cod in worton MD
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 4 beds, 3 bathrooms
5–10 Jul