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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
13–18 Jul
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4.96 out of 5 average rating, 290 reviews
Top guest favourite
Home in Chester
Island Blue Getaway
5.0 out of 5 average rating, 14 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
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
Guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
4.91 out of 5 average rating, 110 reviews, 2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4.88 out of 5 average rating, 24 reviews, 4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
Home in Chester
Farmhouse by the Sea *Pool Pass*
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
Guest favourite
Home in Chester
Kent Island Escape
4.97 out of 5 average rating, 37 reviews, 2 bedrooms, 4 beds, 2 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, 143 reviews, 3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
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
19–24 Jul
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
11–16 Aug
Guest favourite
Home in Stevensville
Cozy home with Screened Porch, Min from Weddings
4.98 out of 5 average rating, 84 reviews, 3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
4.95 out of 5 average rating, 305 reviews, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Guest house in Stevensville
Private | Near BayBridge | Wedding Venue Proximity
5.0 out of 5 average rating, 60 reviews, 2 beds, 1 bathroom
13–18 Jul
Top guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
5.0 out of 5 average rating, 48 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Rooms in Stevensville
Private 2 bedroom suite
4.98 out of 5 average rating, 80 reviews, 2 bedrooms, 2 queen beds, 1 bathroom
26–31 Jul
Superhost
Home in Chester
Waterfront | Hot Tub, Fire Pit & Views
4.89 out of 5 average rating, 19 reviews, 2 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
4.99 out of 5 average rating, 352 reviews, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Cottage in Stevensville
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay
4.98 out of 5 average rating, 49 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Aug