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Search results; 529 homes in Chestertown

Top guest favourite
Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
4 bedrooms, 5 beds, 4 private bathrooms
3–8 Aug
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4.99 out of 5 average rating, 115 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, 33 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, 240 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
4.95 out of 5 average rating, 64 reviews
Top guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
4.95 out of 5 average rating, 107 reviews
Top guest favourite
Flat in Chestertown
Last-Minute Retreat Center of C’town -1 night stay
1 bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 30 reviews
Top guest favourite
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, 93 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, 84 reviews
Top guest favourite
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, 179 reviews
Home in Chestertown
Riverside at Pear Tree Point | Waterfront Escape
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
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
Top guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 145 reviews
Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
5 bedrooms, 11 beds, 3 bathrooms
20–25 May
4.96 out of 5 average rating, 104 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Home in Chestertown
Waterfront Home with Private Dock | Peaceful Stay
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 85 reviews
Home in Chestertown
Pet-Friendly Home on Chester River w/ Dock!
4 bedrooms, 9 beds, 4.5 bathrooms
24–29 Sept
4.7 out of 5 average rating, 10 reviews
Top guest favourite
Apartment in Betterton
Beach Haven Hideaway ~ stunning water views!
2 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Rock Hall
Pene Lane
3 bedrooms, 4 beds, 1.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 11 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