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Search results; Over 1,000 homes in Chester

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, 14 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
Top guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds, 2 bathrooms
11–16 Aug
4.96 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
13–18 Jul
4.96 out of 5 average rating, 290 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, 143 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
Home in Chester
The Fitz Inn
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.96 out of 5 average rating, 80 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
Home in Chester
Farmhouse by the Sea *Pool Pass*
4 bedrooms, 4 beds, 2.5 bathrooms
18–23 Jul
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
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
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, 351 reviews
Top guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
3 bedrooms, 5 beds, 2.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 48 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
Guest favourite
Home in Grasonville
*NewHotTub*LuxuryCoastal*CloseToWeddingVenues
4 bedrooms, 5 beds, 3.5 bathrooms
12–17 Jul
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Guest house in Stevensville
22 Acre Waterfront Retreat.
1 bedroom, 3 beds, 1 bathroom
30 Jul – 4 Aug
5.0 out of 5 average rating, 62 reviews
Superhost
Home in Chester
Waterfront | Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
4.89 out of 5 average rating, 19 reviews
Guest favourite
Home in Grasonville
Private Waterfront Home W/ Hot Tub, Dock & Kayaks
3 bedrooms, 3 queen beds, 2 bathrooms
12–17 Jul
4.95 out of 5 average rating, 305 reviews