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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 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.88 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
16–21 Aug
4.96 out of 5 average rating, 293 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
Top guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 112 reviews
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
4.9 out of 5 average rating, 20 reviews
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.97 out of 5 average rating, 39 reviews
Home in Chester
Farmhouse by the Sea. Yacht Club Pool Pass!
4 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Top 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
Home in Chester
Island Blue Getaway
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest house in Stevensville
Private | Near BayBridge | Wedding Venue Proximity
2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 62 reviews
Superhost
Home in Stevensville
Island Life 2 2024 Remodeled Home
3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
New place to stay
Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
3 bedrooms, 5 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 50 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, 145 reviews
Guest favourite
Home in Stevensville
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
4 bedrooms, 7 beds, 2.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 353 reviews
Top guest favourite
Home in Stevensville
Charming Rancher | Bay Bridge | Near Wedding Venue
4 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest house in Stevensville
Private Guesthouse | 7-acres | Near wedding venues
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds, 2 bathrooms
16–21 Aug
4.95 out of 5 average rating, 307 reviews