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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
8–13 Jul
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4.96 out of 5 average rating, 289 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, 80 reviews
Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.88 out of 5 average rating, 24 reviews
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 bathrooms
30 Aug – 4 Sept
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Chester
Island Blue Getaway
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Home in Grasonville
Bay Breeze - 3BR Waterfront Chester River Retreat
3 bedrooms, 4 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 85 reviews
Top guest favourite
Guest suite in Grasonville
Heron's Haven
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 131 reviews
Guest favourite
Home in Stevensville
Big Yard | Porch | Guesthouse | Near Bay Bridge
4 bedrooms, 7 beds, 3 bathrooms
26–31 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
3 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 142 reviews
Home in Stevensville
Eastern Bay Breeze Retreat
4 bedrooms, 5 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest house in Stevensville
Private | Near BayBridge | Wedding Venue Proximity
2 beds, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 59 reviews
Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
4.91 out of 5 average rating, 110 reviews
Top guest favourite
Room in Stevensville
Rustic & Elegant Private Bed & Bath
1 bed, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 298 reviews
Top guest favourite
Cottage in Stevensville
Chic 3 BR / 2 BA Cottage Near Chesapeake Bay
3 bedrooms, 4 beds, 2 bathrooms
20–25 Jul
4.98 out of 5 average rating, 48 reviews
Guest favourite
Room in Queenstown
The Logan
3 beds, 3 bathrooms
7–12 Jul
4.9 out of 5 average rating, 51 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds, 2 bathrooms
27 Jul – 1 Aug
4.96 out of 5 average rating, 26 reviews
Guest favourite
Home in Stevensville
Cozy home with Screened Porch, Min from Weddings
3 bedrooms, 4 beds, 2 bathrooms
12–17 Jul
4.98 out of 5 average rating, 84 reviews