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Search results; Over 1,000 homes in Chester

Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4.88 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
4.96 out of 5 average rating, 293 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Home in Chester
The Fitz Inn
4.96 out of 5 average rating, 80 reviews, 1 bedroom, 2 beds, 1 bathroom
24–29 Aug
Top guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
4.91 out of 5 average rating, 112 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
4.9 out of 5 average rating, 20 reviews, 2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Guest favourite
Home in Chester
Kent Island Escape
4.97 out of 5 average rating, 39 reviews, 2 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
Top guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4.96 out of 5 average rating, 26 reviews, 4 bedrooms, 5 beds, 2 bathrooms
15–20 Aug
Superhost
Home in Stevensville
Island Life 2 2024 Remodeled Home
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Guest house in Stevensville
Private | Near BayBridge | Wedding Venue Proximity
5.0 out of 5 average rating, 62 reviews, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Chester
Island Blue Getaway
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Home in Chester
Farmhouse by the Sea. Yacht Club Pool Pass!
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Rooms in Stevensville
Private 2 bedroom suite
4.98 out of 5 average rating, 81 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
Home in Chester
Kent Island 4 BR 2.5B Near Water
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
Top guest favourite
Home in Grasonville
Bay Breeze - 3BR Waterfront Chester River Retreat
5.0 out of 5 average rating, 86 reviews, 3 bedrooms, 4 beds, 3 bathrooms
16–21 Aug
Top guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
4.98 out of 5 average rating, 50 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
4.99 out of 5 average rating, 145 reviews, 3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Kent Narrows
Chester Riverfront At Kent Narrows
5.0 out of 5 average rating, 324 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Oct
Top guest favourite
Home in Stevensville
Charming Rancher | Bay Bridge | Near Wedding Venue
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 4 beds, 2 bathrooms
1–6 Aug