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Search results; 290 homes in Chestertown

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Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bathroom
7–12 Nov
4.97 out of 5 average rating, 304 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
18–23 Oct
4.97 out of 5 average rating, 103 reviews
Photo 1 of 29
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 bathrooms
18–23 Oct
5.0 out of 5 average rating, 255 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, 197 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 148 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 81 reviews
Photo 1 of 29
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Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 144 reviews
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 102 reviews
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Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
10–15 Nov
4.96 out of 5 average rating, 140 reviews
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Home in Chestertown
River front cottage with private dock & water fun
5 bedrooms, 11 beds, 3 bathrooms
1–6 Oct
4.96 out of 5 average rating, 106 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, 256 reviews
Photo 1 of 29
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Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds, 3.5 bathrooms
5–10 Oct
4.98 out of 5 average rating, 63 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 29
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Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
4.93 out of 5 average rating, 41 reviews
Photo 1 of 29
Top guest favourite
Home in Chestertown
The Patriot House-Chestertown, MD
6 bedrooms, 7 beds, 3 bathrooms
4–9 Oct
4.96 out of 5 average rating, 137 reviews
Photo 1 of 29
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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
Photo 1 of 29
Guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
2–7 Oct
4.95 out of 5 average rating, 120 reviews
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Flat in Chestertown
Charming Apartment in the heart of Chestertown
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
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