Search results; 373 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 private bathroom
22–27 Jul
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4.98 out of 5 average rating, 197 reviews
Top guest favourite
Home in Chestertown
Gorgeous home in town center & 4 blocks from WAC
5 bedrooms, 6 beds, 4 bathrooms
5–10 Jul
5.0 out of 5 average rating, 241 reviews
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Flat in Chestertown
Secluded and romantic getaway in Chestertown
2 king beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 282 reviews
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
11–16 Aug
4.98 out of 5 average rating, 180 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
4.96 out of 5 average rating, 67 reviews
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Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
10–15 Jul
4.96 out of 5 average rating, 137 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.98 out of 5 average rating, 82 reviews
Superhost
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4 bedrooms, 5 beds, 2.5 bathrooms
5–10 Jul
4.93 out of 5 average rating, 85 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 12 reviews
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 133 reviews
Guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
4.91 out of 5 average rating, 35 reviews
Top guest favourite
Home in Worton
Cozy Cape Cod in worton MD
3 bedrooms, 4 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Chestertown
In Town Chestertown Rancher (1 Block to College)
3 bedrooms, 5 beds, 2 bathrooms
7–12 Jul
5.0 out of 5 average rating, 54 reviews
Guest favourite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
3 bedrooms, 7 beds, 2 bathrooms
22–27 Sept
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Home in Chestertown
Duchess of Kent: Walk to downtown & College
5 bedrooms, 8 beds, 2.5 bathrooms
11–16 Jul
4.98 out of 5 average rating, 208 reviews
Top guest favourite
Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
4 bedrooms, 5 beds, 4 bathrooms
20–25 Sept
4.99 out of 5 average rating, 115 reviews