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Search results; Over 1,000 places in Chester

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Guest favourite
Room in Chester
Stay with LisaHosting for 8 years,
Peaceful Waterfront retreat for Rest & Relaxation
20–25 Apr
4.98 out of 5 average rating, 206 reviews
Guest favourite
Home in Chester
Waterfront Farmhouse Meets Modern Luxury
Hosted by Kevin
3–8 Nov
4.98 out of 5 average rating, 57 reviews
Guest favourite
Home in Stevensville
Kent Island Waterfront Home
Hosted by Natividad
5–10 May
4.73 out of 5 average rating, 11 reviews
Home in Chester
The Fitz Inn
Hosted by Jennifer
1–6 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Chester
Chester Delight- Fireplace/Deck&Patio+fenced yard
Hosted by Julia
20–25 Apr
5.0 out of 5 average rating, 40 reviews
Guest favourite
Guest house in Stevensville
Kozy Kottage on Kent Island, mins from Bay Bridge
Hosted by a business
21–26 Apr
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Chester
*Waterfront Sunset Bayview* sleeps 6
Hosted by Jeremiah
5–10 May
5.0 out of 5 average rating, 11 reviews
Superhost
Flat in Chester
Coastal Kent Narrows Home on Bay
Hosted by Brandon
27 Apr – 2 May
4.93 out of 5 average rating, 15 reviews
Guest favourite
Guest suite in Grasonville
Heron's Haven
Hosted by Laura
12–17 May
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
Hosted by Micheal
20–25 Apr
4.85 out of 5 average rating, 48 reviews
Guest favourite
Guest house in Chester
Waterfront Guest Cottage: Sunsets, Pool, Pier
Hosted by Diane
20–25 Apr
5.0 out of 5 average rating, 39 reviews
Guest favourite
Flat in Chester
Cozy Waterfront Apartment Chester, MD
Hosted by Jordan
13–18 Jun
4.97 out of 5 average rating, 234 reviews
Guest favourite
Houseboat in Kent Narrows
Cass-N-Reel Luxury Houseboat
Hosted by a business
13–18 Jul
4.97 out of 5 average rating, 67 reviews
Guest favourite
Home in Stevensville
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Hosted by a business
2–7 Jun
4.94 out of 5 average rating, 191 reviews
Guest favourite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
Hosted by Kelly
22–27 Apr
5.0 out of 5 average rating, 79 reviews
Guest favourite
Houseboat in Grasonville
Cass-Away A Luxury Houseboat
Hosted by a business
6–11 May
4.99 out of 5 average rating, 115 reviews
Guest favourite
Home in Chester
Waterfront Paradise to Work or Rest
Hosted by Blanche
6–11 May
4.94 out of 5 average rating, 35 reviews
Guest favourite
Home in Stevensville
Kozy Kent Island Home w/screened porch
Hosted by a business
6–11 May
5.0 out of 5 average rating, 5 reviews