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Search results; 306 homes in Chestertown

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Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 1 bed, 1 private bathroom
1–6 Mar
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4.98 out of 5 average rating, 202 reviews
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Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 301 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 101 reviews
Photo 1 of 29
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
2–7 Nov
4.98 out of 5 average rating, 196 reviews
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 bathrooms
20–25 Sept
5.0 out of 5 average rating, 253 reviews
Photo 1 of 16
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 79 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.99 out of 5 average rating, 146 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, 255 reviews
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Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
12–17 Oct
4.96 out of 5 average rating, 139 reviews
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Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 144 reviews
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Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
3 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.91 out of 5 average rating, 67 reviews
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Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 12 reviews
Photo 1 of 29
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Flat in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 154 reviews
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Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 bathrooms
2–7 Nov
5.0 out of 5 average rating, 17 reviews
Photo 1 of 26
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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 Sept
4.98 out of 5 average rating, 126 reviews
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 101 reviews
Photo 1 of 29
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Home in Chestertown
The Patriot House-Chestertown, MD
6 bedrooms, 7 beds, 3 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 135 reviews
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Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
12–17 Oct
4.86 out of 5 average rating, 196 reviews
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Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 71 reviews