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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 bed, 1 private bathroom
16–21 Aug
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4.96 out of 5 average rating, 297 reviews
Top guest favourite
Home in Chester
The Fitz Inn
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 82 reviews
Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.89 out of 5 average rating, 27 reviews
Home in Chester
NEW I Waterfront, HotTub, Dock, Fire Pit, GameRoom
4 bedrooms, 4 king beds, 3.5 bathrooms
30 Aug – 4 Sept
New place to stay
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
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, 1 bathroom
17–22 Aug
4.91 out of 5 average rating, 114 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 422 reviews
Top guest favourite
Home in Kent Narrows
Chester Riverfront At Kent Narrows
2 bedrooms, 4 beds, 1 bathroom
2–7 Oct
5.0 out of 5 average rating, 325 reviews
Guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Guest house in Stevensville
Private | Near BayBridge | Wedding Venue Proximity
2 beds, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Flat in Stevensville
Heron Roost
2 bedrooms, 2 beds, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 92 reviews
Home in Pasadena
Cozy Riviera Beach Retreat Near BWI & Annapolis
3 bedrooms, 3 beds, 1.5 bathrooms
19–24 Aug
New place to stay
Top guest favourite
Rooms in Stevensville
Private 2 bedroom suite
2 bedrooms, 2 queen beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 359 reviews
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Queenstown
Gorgeous Creek Side Ranch-Style Estate With Dock
4 bedrooms, 6 beds, 2.5 bathrooms
17–22 Aug
4.98 out of 5 average rating, 62 reviews
Home in Stevensville
Kent Island Getaway with Fire Pit Near Annapolis
3 bedrooms, 3 beds, 2.5 bathrooms
12–17 Aug
New place to stay
Superhost
Home in Stevensville
Island Life 2 2024 Remodeled Home
3 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
New place to stay