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Search results; 309 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 private bathroom
2–7 Nov
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4.99 out of 5 average rating, 251 reviews
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Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
4.97 out of 5 average rating, 286 reviews, 2 beds, 1 bathroom
24–29 Jul
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Home in Chestertown
High Tide & Hound
4.98 out of 5 average rating, 85 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
4.99 out of 5 average rating, 136 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
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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
Superhost
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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Home in Chestertown
Charming Haven on High
4.96 out of 5 average rating, 69 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
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Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
4.92 out of 5 average rating, 186 reviews, 1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 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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Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
5.0 out of 5 average rating, 148 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Aug – 1 Sept
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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
Lovely Home in Chestertown With Free EV Charging
5.0 out of 5 average rating, 96 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Aug
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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
Flat in Chestertown
1-br apt in downtown Chestertown (Unit 1)
4.91 out of 5 average rating, 97 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
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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
Chesapeake Getaway | Marinas | Woodland Views
4.88 out of 5 average rating, 32 reviews, 3 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
Guest house in Chestertown
Casa Cannon
5 bedrooms, 5 beds, 2 bathrooms
23–28 Jul
Guest favourite
Room in Chestertown
Private Bedroom and bath in Chestertown, MD
4.88 out of 5 average rating, 158 reviews, 1 double bed, 1 bathroom
24–29 Jul
Top guest favourite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
4.97 out of 5 average rating, 101 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Aug