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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
16–21 Aug
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4.96 out of 5 average rating, 296 reviews
Home in Chester
NEW I Waterfront, HotTub, Dock, Fire Pit, GameRoom
4 bedrooms, 4 king beds, 3.5 bathrooms
23–28 Aug
New place to stay
Guest favourite
Home in Chester
Crab Alley | Waterfront Home + Hot Tub + Game Room
4 bedrooms, 5 beds, 2 bathrooms
31 Aug – 5 Sept
4.88 out of 5 average rating, 26 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
9–14 Aug
4.91 out of 5 average rating, 113 reviews
Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 466 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
Home in Pasadena
Waterfront Retreat | Pool, Hot Tub & Creek Views
6 bedrooms, 8 beds, 4 bathrooms
24–29 Aug
New place to stay
Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 bathrooms
5–10 Oct
4.98 out of 5 average rating, 40 reviews
Home in Chester
Farmhouse by the Sea. Yacht Club Pool Pass!
4 bedrooms, 4 beds, 2.5 bathrooms
10–15 Aug
Guest favourite
Home in Stevensville
Cozy home with Screened Porch, Min from Weddings
3 bedrooms, 4 beds, 2 bathrooms
4–9 Aug
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Guest house in Stevensville
Private | Near BayBridge | Wedding Venue Proximity
2 beds, 1 bathroom
10–15 Aug
5.0 out of 5 average rating, 63 reviews
Superhost
Home in Stevensville
Island Life 2 2024 Remodeled Home
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
New place to stay
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
Top guest favourite
Home in Queenstown
Gorgeous Creek Side Ranch-Style Estate With Dock
4 bedrooms, 6 beds, 2.5 bathrooms
17–22 Aug
4.98 out of 5 average rating, 62 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, 308 reviews
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
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 358 reviews