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Search results; Over 1,000 homes in Chester

Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 private bathrooms
20–25 Oct
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4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds, 2 bathrooms
10–15 Sept
4.96 out of 5 average rating, 26 reviews
Home in Chester
Waterfront home w/ HotTub, Dock, FirePit, GameRoom
4 bedrooms, 4 king beds, 3.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chester
Crab Alley: Bayfront Home + Hot Tub & Game Room
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.9 out of 5 average rating, 29 reviews
Top guest favourite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
3 bedrooms, 6 beds, 2 bathrooms
4–9 Oct
4.99 out of 5 average rating, 149 reviews
Top guest favourite
Home in Chester
Island Blue Getaway
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 15 reviews
Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms, 5 beds, 2.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Stevensville
Island Life 2 2024 Remodeled Home
3 bedrooms, 4 beds, 2 bathrooms
14–19 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chester
The Fitz Inn
1 bedroom, 2 beds, 1 bathroom
2–7 Nov
4.96 out of 5 average rating, 83 reviews
Top guest favourite
Houseboat in Grasonville
Cass-Away A Luxury Houseboat
2 bedrooms, 2 queen beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 213 reviews
Top guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 116 reviews
Top guest favourite
Home in Stevensville
Beautiful Kent Island Getaway with Pool
4 bedrooms, 5 beds, 3.5 bathrooms
7–12 Sept
4.97 out of 5 average rating, 131 reviews
Top guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
3 bedrooms, 5 beds, 2.5 bathrooms
7–12 Sept
4.98 out of 5 average rating, 54 reviews
Guest favourite
Rooms in Stevensville
Private 2 bedroom suite
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 81 reviews
Top guest favourite
Home in Grasonville
Bay Breeze - 3BR Waterfront Chester River Retreat
3 bedrooms, 4 beds, 3 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Home in Stevensville
Charming Rancher | Bay Bridge | Near Wedding Venue
4 bedrooms, 4 beds, 2 bathrooms
10–15 Oct
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Queenstown
Gorgeous Creek Side Ranch-Style Estate With Dock
4 bedrooms, 6 beds, 2.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
17–22 Oct
4.96 out of 5 average rating, 301 reviews
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.92 out of 5 average rating, 24 reviews