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Search results; Over 1,000 homes in Chester

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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, 49 reviews
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Guest favourite
Home in Chester
Crab Alley: Bayfront Home + Hot Tub & Game Room
4 bedrooms, 5 beds, 2 bathrooms
26 Sept – 1 Oct
4.87 out of 5 average rating, 31 reviews
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Guest favourite
Home in Chester
200+ Feet of Waterfront on 3 Acres
4 bedrooms, 5 beds, 2 bathrooms
28 Sept – 3 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, 150 reviews
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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
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Superhost
Home in Stevensville
Island Life 2 2024 Remodeled Home
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 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
19–24 Sept
5.0 out of 5 average rating, 7 reviews
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Home in Chester
Kent Island 4 BR 2.5B Near Water
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 118 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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Top guest favourite
Home in Stevensville
Screened Porch | Near Bay Bridge & USNA | Big Yard
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Sept
4.98 out of 5 average rating, 55 reviews
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Superhost
Home in Chester
Waterfront Hot Tub, Fire Pit & Views
2 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.92 out of 5 average rating, 26 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
28 Sept – 3 Oct
4.93 out of 5 average rating, 364 reviews
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Guest favourite
Rooms in Stevensville
Private 2 bedroom suite
2 bedrooms, 2 queen beds, 1 bathroom
27 Sept – 2 Oct
4.98 out of 5 average rating, 81 reviews
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Guest favourite
Townhouse in Queenstown
Golf, Kayaks, Outlets, Water Access, Fire Pit!
3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 8 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, 302 reviews
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Guest favourite
Home in Grasonville
Your Bay Bridge Retreat
4 bedrooms, 4 beds, 2.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 8 reviews
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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
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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