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Search results; 315 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 private bathroom
8–13 Dec
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4.99 out of 5 average rating, 252 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
6–11 Sept
4.97 out of 5 average rating, 89 reviews
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Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bathroom
29 Aug – 3 Sept
4.97 out of 5 average rating, 289 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
14–19 Aug
4.96 out of 5 average rating, 71 reviews
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
15–20 Aug
4.98 out of 5 average rating, 185 reviews
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 247 reviews
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
25–30 Aug
4.96 out of 5 average rating, 114 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 139 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 15 reviews
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Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 150 reviews
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Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 7 reviews
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Home in Betterton
Ruby's Sea Glass Cottage near Betterton Beach
3 bedrooms, 5 beds, 1 bathroom
15–20 Aug
4.99 out of 5 average rating, 70 reviews
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Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 7 reviews
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Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 142 reviews
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 98 reviews
Guest favourite
Home in Chestertown
River Cottage, Chestertown
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.94 out of 5 average rating, 47 reviews
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Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4 bedrooms, 5 beds, 2.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 88 reviews
Guest favourite
Home in Rock Hall
Chesapeake Bay Retreat W/Breathtaking Views
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
4.94 out of 5 average rating, 31 reviews
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Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds, 3.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 60 reviews