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Search results; 295 homes in Chestertown

Guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 private bathrooms
28 Sept – 3 Oct
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4.96 out of 5 average rating, 118 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, 252 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, 300 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 99 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, 194 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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Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
11–16 Sept
4.96 out of 5 average rating, 139 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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Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 144 reviews
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Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 11 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
Guest favourite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
3 bedrooms, 7 beds, 2 bathrooms
1–6 Nov
4.91 out of 5 average rating, 67 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
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Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds, 3.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 62 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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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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Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 9 reviews
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Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
4 bedrooms, 5 beds, 4 bathrooms
20–25 Sept
4.97 out of 5 average rating, 118 reviews