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Search results; Over 1,000 homes in Chester

Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed
16–21 Aug
4.96 out of 5 average rating, 297 reviews
Home in Chester
NEW I Waterfront, HotTub, Dock, Fire Pit, GameRoom
4 bedrooms, 4 king beds
30 Aug – 4 Sept
New place to stay
Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4 bedrooms, 5 beds
26 Sept – 1 Oct
4.89 out of 5 average rating, 27 reviews
Top guest favourite
Home in Chester
The Fitz Inn
1 bedroom, 2 beds
24–29 Aug
4.96 out of 5 average rating, 82 reviews
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds
3–8 Sept
4.91 out of 5 average rating, 22 reviews
Top guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 bedrooms, 2 beds
17–22 Aug
4.91 out of 5 average rating, 114 reviews
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds
5–10 Oct
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Flat in Stevensville
Boutique by the Bay
1 bedroom, 1 queen bed
16–21 Aug
4.97 out of 5 average rating, 311 reviews
Home in Chester
Eclectic Farmhouse by the Sea. Kent Island.
4 bedrooms, 4 beds
14–19 Aug
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Stevensville
Cozy home with Screened Porch, Min from Weddings
3 bedrooms, 4 beds
12–17 Aug
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds
12–17 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds
15–20 Aug
4.96 out of 5 average rating, 26 reviews
Home in Glen Burnie
DMV Themed 4BR Near BWI Airport
4 bedrooms, 5 beds
16–21 Aug
New place to stay
Top guest favourite
Home in Chester
Island Blue Getaway
3 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms, 5 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Home in Stevensville
Kent Island Getaway with Fire Pit Near Annapolis
3 bedrooms, 3 beds
12–17 Aug
New place to stay
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds
16–21 Aug
4.95 out of 5 average rating, 308 reviews
Top guest favourite
Home in Stevensville
Chessie Cottage - Chesapeake Bay
2 bedrooms, 4 beds
14–19 Aug
5.0 out of 5 average rating, 35 reviews