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Search results; 329 homes in Chestertown

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Top guest favourite
Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
4 bedrooms, 5 beds, 4 private bathrooms
20–25 Sept
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4.99 out of 5 average rating, 117 reviews
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Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 297 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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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
4.96 out of 5 average rating, 75 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, 253 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 142 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, 95 reviews
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Flat in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
13–18 Nov
5.0 out of 5 average rating, 153 reviews
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
12–17 Oct
4.98 out of 5 average rating, 193 reviews
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Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
1–6 Sept
4.86 out of 5 average rating, 196 reviews
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Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 1 king bed, 1 bathroom
1–6 Dec
4.98 out of 5 average rating, 202 reviews
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Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 70 reviews
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Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bathroom
11–16 Oct
4.92 out of 5 average rating, 191 reviews
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Home in Chestertown
Private Chester River Retreat | Fire Pit & Views
3 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 5 reviews
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Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bathroom
1–6 Sept
4.98 out of 5 average rating, 143 reviews
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Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 9 reviews
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
28 Sept – 3 Oct
4.96 out of 5 average rating, 117 reviews
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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, 102 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, 99 reviews