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Search results; 304 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 1 bed, 1 private bathroom
1–6 Mar
,
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
27 Sept – 2 Oct
4.97 out of 5 average rating, 301 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
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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
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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, 145 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
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
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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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
Guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.95 out of 5 average rating, 120 reviews
Home in Chestertown
Riverfront Retreat
6 bedrooms, 11 beds, 5.5 bathrooms
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 104 reviews
Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
5 bedrooms, 11 beds, 3 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 105 reviews
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Flat in Chestertown
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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Flat in Chestertown
RIVER WATCH
3 bedrooms, 3 queen beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 122 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
Top guest favourite
Home in Worton
Farm House w/ Water Access (near Chestertown)
4 bedrooms, 7 beds, 3 bathrooms
16–21 Sept
4.99 out of 5 average rating, 78 reviews
Guest favourite
Home in Chestertown
The Portside Manor - Queen Street Chestertown
3 bedrooms, 4 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Guest house in Chestertown
Piney Grove 2 Bedroom Carriage House Apartment
2 bedrooms, 3 beds, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 53 reviews