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Search results; Over 1,000 homes in Chester

Top guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 private bathrooms
20–25 Oct
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4.98 out of 5 average rating, 46 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
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, 4 reviews
Top guest favourite
Home in Chester
The Fitz Inn
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.96 out of 5 average rating, 82 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
Featured hotel
Room in St. Michaels
Standard queen room
1 queen bed, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Room in Queenstown
The Logan
3 beds, 3 bathrooms
5–10 Sept
4.91 out of 5 average rating, 53 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, 139 reviews
Top guest favourite
Flat in Grasonville
Halcyon house. Lovely views on MD eastern shore.
1 bedroom, 1 king bed, 1 bathroom
8–13 Sept
4.91 out of 5 average rating, 235 reviews
Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms, 5 beds, 2.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 3 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, 3 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
Guest favourite
Guest suite in Stevensville
Kent Island Haven - A Waterfront Getaway
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.96 out of 5 average rating, 158 reviews
Guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 26 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, 3 reviews
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 310 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 430 reviews
Top guest favourite
Flat in Stevensville
Boutique by the Bay
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 312 reviews