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Search results; 299 homes in Chestertown

Top guest favorite
Farm stay in Chestertown
Outrange at Blue Heron Farm
2 bedrooms, 2 beds, 1 bath
Aug 15 – 20
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4.96 out of 5 average rating, 163 reviews
Top guest favorite
Apartment in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds, 1 bath
Aug 29 – Sep 3
4.97 out of 5 average rating, 291 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 baths
Sep 6 – 11
4.97 out of 5 average rating, 90 reviews
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 baths
Aug 15 – 20
4.98 out of 5 average rating, 186 reviews
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 247 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 baths
Aug 20 – 25
4.96 out of 5 average rating, 74 reviews
Superhost
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed, 1 bath
Aug 16 – 21
4.86 out of 5 average rating, 196 reviews
Guest favorite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 baths
Aug 13 – 18
5.0 out of 5 average rating, 16 reviews
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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 bath
Aug 17 – 22
4.99 out of 5 average rating, 252 reviews
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Guesthouse in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bath
Aug 13 – 18
4.99 out of 5 average rating, 69 reviews
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 baths
Aug 30 – Sep 4
4.96 out of 5 average rating, 115 reviews
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Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
4.98 out of 5 average rating, 142 reviews
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Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds, 2.5 baths
Aug 20 – 25
4.98 out of 5 average rating, 124 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bath
Aug 25 – 30
4.99 out of 5 average rating, 141 reviews
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Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bath
Aug 27 – Sep 1
5.0 out of 5 average rating, 151 reviews
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Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds, 3.5 baths
Aug 16 – 21
5.0 out of 5 average rating, 60 reviews
Home in Chestertown
Private Chester River Retreat | Fire Pit & Views
3 bedrooms, 6 beds, 2 baths
Aug 18 – 23
5.0 out of 5 average rating, 4 reviews
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 baths
Sep 13 – 18
5.0 out of 5 average rating, 99 reviews
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Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4 bedrooms, 5 beds, 2.5 baths
Aug 16 – 21
4.93 out of 5 average rating, 89 reviews