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Search results; Over 1,000 homes in Chester

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Guest favourite
Home in Chester
A waterfront Paradise with hot tub
3 bedrooms, 3 beds, 2 private bathrooms
9–14 Nov
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4.95 out of 5 average rating, 65 reviews
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Top guest favourite
Home in Chester
Island Blue Getaway
3 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Home in Chester
Crab Alley | Bayfront Hot Tub & Game Room
4 bedrooms, 5 beds, 2 bathrooms
19–24 Oct
4.88 out of 5 average rating, 32 reviews
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Top guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 119 reviews
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Guest favourite
Home in Stevensville
Island Life 2 2024 Remodeled Home
3 bedrooms, 4 beds, 2 bathrooms
8–13 Nov
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds, 2 bathrooms
13–18 Oct
4.96 out of 5 average rating, 26 reviews
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Top guest favourite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
3 bedrooms, 6 beds, 2 bathrooms
26–31 Oct
4.99 out of 5 average rating, 152 reviews
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Top guest favourite
Home in Chester
Waterfront home w/ HotTub, Dock, FirePit, GameRoom
4 bedrooms, 4 king beds, 3.5 bathrooms
17–22 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Houseboat in Grasonville
Cass-Away A Luxury Houseboat
2 bedrooms, 2 queen beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 215 reviews
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Top guest favourite
Home in Chester
The Fitz Inn
1 bedroom, 2 beds, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 84 reviews
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Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms, 5 beds, 2.5 bathrooms
11–16 Oct
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
1 bedroom, 1 queen bed, 1 bathroom
28 Oct – 2 Nov
4.96 out of 5 average rating, 304 reviews
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Home in Stevensville
Beautiful three bedroom Kent Island home.
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
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Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
4.89 out of 5 average rating, 27 reviews
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Guest favourite
Home in Stevensville
Charming Coastal/Country Home w/3 Acres & Sauna!
4 bedrooms, 7 beds, 2.5 bathrooms
17–22 Oct
4.93 out of 5 average rating, 367 reviews
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Superhost
Home in Stevensville
Kent Island Luxury Waterfront
4 bedrooms, 10 beds, 3.5 bathrooms
18–23 Oct
4.63 out of 5 average rating, 38 reviews
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Guest favourite
Home in Chester
Kent Island Escape
2 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
4.94 out of 5 average rating, 52 reviews
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Top guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
3 bedrooms, 5 beds, 2.5 bathrooms
17–22 Oct
4.98 out of 5 average rating, 55 reviews
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Guest favourite
Home in Queenstown
Gorgeous Creek Side Ranch-Style Estate With Dock
4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
4.98 out of 5 average rating, 63 reviews