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Search results; 310 homes in Chestertown

Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
5 bedrooms, 11 beds, 3 private bathrooms
28 Sept – 3 Oct
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4.96 out of 5 average rating, 105 reviews
Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 291 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds
24–29 Aug
4.98 out of 5 average rating, 188 reviews
Top guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds
30 Aug – 4 Sept
4.96 out of 5 average rating, 115 reviews
Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 247 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds
6–11 Sept
4.97 out of 5 average rating, 90 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds
20–25 Aug
4.96 out of 5 average rating, 74 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds
14–19 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds
8–13 Dec
4.99 out of 5 average rating, 253 reviews
Home in Chestertown
Private Chester River Retreat | Fire Pit & Views
3 bedrooms, 6 beds
18–23 Aug
5.0 out of 5 average rating, 4 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed
16–21 Aug
4.86 out of 5 average rating, 196 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds
23–28 Aug
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds
15–20 Aug
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Chestertown
Waterfront Wellness - *With Pool and Hot Tub!*
4 bedrooms, 5 beds
22–27 Aug
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds
25–30 Aug
4.99 out of 5 average rating, 141 reviews
Top guest favourite
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 7 reviews
Home in Chestertown
3BR Home | Close to Washington College & Downtown
3 bedrooms, 4 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Betterton
Ruby's Sea Glass Cottage near Betterton Beach
3 bedrooms, 5 beds
15–20 Aug
4.99 out of 5 average rating, 71 reviews
Top guest favourite
Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 99 reviews