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Search results; Over 1,000 homes in Chester

Guest favourite
Home in Chester
Crab Alley: Bayfront Home + Hot Tub & Game Room
4 bedrooms, 5 beds, 2 private bathrooms
26 Sept – 1 Oct
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4.87 out of 5 average rating, 31 reviews
Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
28 Oct – 2 Nov
4.96 out of 5 average rating, 301 reviews
Top guest favourite
Home in Chester
Waterfront home w/ HotTub, Dock, FirePit, GameRoom
4 bedrooms, 4 king beds, 3.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Guest suite in Grasonville
Heron's Haven
1 bedroom, 1 bed, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 140 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
Room in Chester
Master Suite in farmhouse by the sea. *Pool Pass*
1 king bed, 1 bathroom
16–21 Sept
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, 84 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 Kent Narrows
Chester Riverfront At Kent Narrows
2 bedrooms, 4 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 328 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
Rooms in Stevensville
Private 2 bedroom suite
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 81 reviews
Home in Stevensville
Beautiful three bedroom Kent Island home.
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Sept
Home in Stevensville
Kent Island Getaway with Fire Pit Near Annapolis
3 bedrooms, 3 beds, 2.5 bathrooms
14–19 Sept
New place to stay
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
Room in Chester
Room for an Island getaway
1 bed, 1 bathroom
15–20 Sept
Top guest favourite
Home in Stevensville
Private & Peaceful Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
21–26 Sept
5.0 out of 5 average rating, 5 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
Top guest favourite
Flat in Grasonville
Halcyon house. Lovely views on MD eastern shore.
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.91 out of 5 average rating, 237 reviews
Guest favourite
Home in Stevensville
Big Yard | Porch | Guesthouse | Near Bay Bridge
4 bedrooms, 7 beds, 3 bathrooms
25–30 Oct
5.0 out of 5 average rating, 13 reviews