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Search results; 307 homes in Chestertown

Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 private bathrooms
30 Aug – 4 Sept
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5.0 out of 5 average rating, 248 reviews
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Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 292 reviews
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
24–29 Aug
4.98 out of 5 average rating, 188 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, 91 reviews
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 115 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Aug
4.96 out of 5 average rating, 75 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 16 reviews
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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 bathroom
8–13 Dec
4.99 out of 5 average rating, 253 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
Home in Chestertown
Private Chester River Retreat | Fire Pit & Views
3 bedrooms, 6 beds, 2 bathrooms
18–23 Aug
5.0 out of 5 average rating, 4 reviews
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Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
4.99 out of 5 average rating, 69 reviews
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Home in Worton
Cozy Cape Cod in worton MD
3 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 22 reviews
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Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
17–22 Aug
4.96 out of 5 average rating, 139 reviews
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Home in Chestertown
Waterfront Wellness - *With Pool and Hot Tub!*
4 bedrooms, 5 beds, 3.5 bathrooms
22–27 Aug
4.96 out of 5 average rating, 28 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.99 out of 5 average rating, 141 reviews
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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, 33 reviews
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Home in Betterton
Ruby's Sea Glass Cottage near Betterton Beach
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 71 reviews
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Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds, 2.5 bathrooms
20–25 Aug
4.98 out of 5 average rating, 124 reviews
Top guest favourite
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, 99 reviews