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Search results; Over 1,000 places in Chester

Guest favorite
Room in Chester
Stay with LisaHosting for 8 years,
Peaceful Waterfront retreat for Rest & Relaxation
Apr 19 – 24
4.98 out of 5 average rating, 206 reviews
Home in Chester
The Fitz Inn
2 beds
May 6 – 11
5.0 out of 5 average rating, 4 reviews
Guest favorite
Guesthouse in Stevensville
Kozy Kottage on Kent Island, mins from Bay Bridge
2 beds
Apr 21 – 26
5.0 out of 5 average rating, 5 reviews
Guest favorite
Home in Chester
*Waterfront Sunset Bayview* sleeps 6
4 beds
Apr 18 – 23
5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 beds
Apr 18 – 23
4.85 out of 5 average rating, 48 reviews
Superhost
Apartment in Chester
Coastal Kent Narrows Home on Bay
3 beds
Apr 27 – May 2
4.93 out of 5 average rating, 15 reviews
Guest favorite
Home in Chester
Chester Delight- Fireplace/Deck&Patio+fenced yard
6 beds
Apr 18 – 23
5.0 out of 5 average rating, 40 reviews
Guest favorite
Guesthouse in Grasonville
Eastern Shore Charm on Winchester Creek
1 queen bed
Apr 18 – 23
4.9 out of 5 average rating, 203 reviews
Guest favorite
Home in Stevensville
Kent Island Waterfront Home
4 beds
Apr 21 – 26
4.73 out of 5 average rating, 11 reviews
Guest favorite
Home in Chester
Waterfront Farmhouse Meets Modern Luxury
6 beds
Nov 3 – 8
4.98 out of 5 average rating, 56 reviews
Guest favorite
Guesthouse in Chester
Waterfront Guest Cottage: Sunsets, Pool, Pier
6 beds
Apr 18 – 23
5.0 out of 5 average rating, 39 reviews
Guest favorite
Apartment in Chester
Cozy Waterfront Apartment Chester, MD
1 queen bed
Jun 13 – 18
4.97 out of 5 average rating, 234 reviews
Guest favorite
Home in Chester
Waterfront Paradise to Work or Rest
3 beds
May 6 – 11
4.94 out of 5 average rating, 35 reviews
Guest favorite
Home in Chester
Kent Island Time-Waterfront
4 beds
Apr 18 – 23
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Stevensville
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
6 beds
Jun 2 – 7
4.94 out of 5 average rating, 191 reviews
Guest favorite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
5 beds
Apr 22 – 27
5.0 out of 5 average rating, 79 reviews
Guest favorite
Home in Grasonville
River Front, Private Single Family Home
3 queen beds
Apr 21 – 26
4.94 out of 5 average rating, 224 reviews
Guest favorite
Home in Grasonville
Bay Breeze-Chester River Retreat
4 beds
Jun 2 – 7
5.0 out of 5 average rating, 22 reviews