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Search results; 299 homes in Chestertown

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Guest house in Chestertown
Cozy Carriage House
Studio, 1 bed, 1 private bathroom
10–15 Aug
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4.87 out of 5 average rating, 195 reviews
Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bathroom
20–25 Aug
4.97 out of 5 average rating, 286 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.98 out of 5 average rating, 85 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.99 out of 5 average rating, 136 reviews
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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.99 out of 5 average rating, 251 reviews
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Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
4.98 out of 5 average rating, 199 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
4.96 out of 5 average rating, 69 reviews
Guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 Aug
4.92 out of 5 average rating, 186 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 148 reviews
Top guest favourite
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, 181 reviews
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Aug
5.0 out of 5 average rating, 96 reviews
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Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds, 2.5 bathrooms
26–31 Jul
4.98 out of 5 average rating, 123 reviews
Guest favourite
Flat in Chestertown
1-br apt in downtown Chestertown (Unit 1)
1 bedroom, 1 queen bed, 1 bathroom
21–26 Jul
4.91 out of 5 average rating, 97 reviews
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Home in Chestertown
Chesapeake Getaway | Marinas | Woodland Views
3 bedrooms, 4 beds, 2 bathrooms
21–26 Jul
4.88 out of 5 average rating, 32 reviews
Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 bathrooms
25–30 Aug
5.0 out of 5 average rating, 244 reviews
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
1 double bed, 1 bathroom
24–29 Jul
4.88 out of 5 average rating, 158 reviews
Top guest favourite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 bedroom, 1 queen bed, 1 bathroom
7–12 Aug
4.97 out of 5 average rating, 101 reviews