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Search results; 301 homes in Chestertown

Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
Studio, 2 beds, 1 private bathroom
27 Jul – 1 Aug
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4.97 out of 5 average rating, 286 reviews
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Home in Chestertown
Charming Haven on High
4.96 out of 5 average rating, 68 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
19–24 Jul
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Home in Chestertown
High Tide & Hound
4.98 out of 5 average rating, 84 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
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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
9–14 Aug
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Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
5.0 out of 5 average rating, 147 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5.0 out of 5 average rating, 244 reviews, 5 bedrooms, 6 beds, 4 bathrooms
25–30 Aug
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
4.98 out of 5 average rating, 181 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
4.95 out of 5 average rating, 110 reviews, 3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
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Home in Chestertown
Classic Victorian in Chestertown
4.96 out of 5 average rating, 138 reviews, 4 bedrooms, 8 beds, 2.5 bathrooms
17–22 Jul
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Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
4.98 out of 5 average rating, 64 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Jul
Guest favourite
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Top guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
4.98 out of 5 average rating, 123 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
5.0 out of 5 average rating, 14 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
10–15 Aug
Guest favourite
Home in Rock Hall
Chesapeake Bay Retreat W/Breathtaking Views
4.93 out of 5 average rating, 29 reviews, 3 bedrooms, 5 beds, 2 bathrooms
19–24 Jul
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Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
4.97 out of 5 average rating, 35 reviews, 3 bedrooms, 6 beds, 3 bathrooms
17–22 Jul
Guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4.93 out of 5 average rating, 86 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
17–22 Jul
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Home in Worton
Cozy Cape Cod in worton MD
5.0 out of 5 average rating, 17 reviews, 3 bedrooms, 4 beds, 3 bathrooms
2–7 Aug
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Home in Rock Hall
Historic Cottage | 1min DT | Views | W/D | Parking
4.94 out of 5 average rating, 66 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
4.99 out of 5 average rating, 251 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Nov