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Search results; Over 1,000 homes in Chester

Top guest favourite
Home in Chester
Waterfront home w/ HotTub, Dock, FirePit, GameRoom
4 bedrooms, 4 king beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 301 reviews
Top guest favourite
Home in Grasonville
Bay Breeze - 3BR Waterfront Chester River Retreat
3 bedrooms, 4 beds, 3 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Home in Chester
The Fitz Inn
1 bedroom, 2 beds, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 83 reviews
Superhost
Home in Stevensville
Private & Peaceful Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Chester
Crab Alley: Bayfront Home + Hot Tub & Game Room
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.9 out of 5 average rating, 29 reviews
Superhost
Home in Stevensville
Island Life 2 2024 Remodeled Home
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Houseboat in Kent Narrows
Cass-N-Reel Luxury Houseboat
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 187 reviews
Guest favourite
Houseboat in Stevensville
Chesapeake Houseboat Getaway
2 bedrooms, 3 beds, 1.5 bathrooms
8–13 Nov
4.87 out of 5 average rating, 78 reviews
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
4.94 out of 5 average rating, 48 reviews
Home in Stevensville
Beautiful three bedroom Kent Island home.
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
Top guest favourite
Home in Stevensville
Eastern Bay Breeze Retreat
4 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Stevensville
Bayview Bungalow - Water view, EV charging station
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 87 reviews
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.92 out of 5 average rating, 26 reviews
Guest favourite
Flat in Stevensville
Kent Island Getaway
1 bedroom, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Rooms in Stevensville
Private 2 bedroom suite
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Cottage in Stevensville
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 51 reviews