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Search results; 300 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, 285 reviews
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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
2–7 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
Charming Haven on High
4.96 out of 5 average rating, 68 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Jul
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Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
4.98 out of 5 average rating, 199 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Aug
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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
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
4.99 out of 5 average rating, 135 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
4.99 out of 5 average rating, 251 reviews, 1 bedroom, 2 beds, 1 bathroom
13–18 Oct
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5.0 out of 5 average rating, 242 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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Guest house in Chestertown
Cozy Carriage House
4.87 out of 5 average rating, 195 reviews, 1 bed, 1 bathroom
10–15 Aug
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Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
4.92 out of 5 average rating, 183 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 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
9–14 Aug
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
20–25 Jul
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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
14–19 Jul
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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
Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
4.96 out of 5 average rating, 105 reviews, 5 bedrooms, 11 beds, 3 bathrooms
20–25 May
Guest favourite
Home in Chestertown
Waterfront 3bed/2.5 bath w/dock&beach close 2 town
4.7 out of 5 average rating, 37 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
14–19 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
14–19 Jul