Over 1,000 places in Chester

Home in Chester
The Fitz Inn
2 beds
Apr 7 – 12
New place to stay
Guest favorite
Home in Chester
*Waterfront Sunset Bayview* sleeps 6
4 beds
Apr 7 – 12
5.0 out of 5 average rating, 8 reviews
Guest favorite
Room in Chester
Stay with LisaHosting for 8 years,
Peaceful Waterfront retreat for Rest & Relaxation
Apr 2 – 7
4.98 out of 5 average rating, 205 reviews
Superhost
Apartment in Chester
Coastal Kent Narrows Home on Bay
3 beds
Apr 5 – 10
4.92 out of 5 average rating, 13 reviews
Guest favorite
Guesthouse in Chester
Waterfront Guest Cottage: Sunsets, Pool, Pier
6 beds
Apr 1 – 6
5.0 out of 5 average rating, 39 reviews
Guest favorite
Houseboat in Kent Narrows
Cass-N-Reel Luxury Houseboat
1 bed
May 19 – 24
4.97 out of 5 average rating, 63 reviews
Guest favorite
Home in Chester
Waterfront Farmhouse Meets Modern Luxury
6 beds
Apr 5 – 10
4.98 out of 5 average rating, 55 reviews
Guest favorite
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 beds
Apr 1 – 6
4.85 out of 5 average rating, 48 reviews
Guest favorite
Home in Chester
Chester Delight- Fireplace/Deck&Patio+fenced yard
6 beds
Apr 15 – 20
5.0 out of 5 average rating, 38 reviews
Guest favorite
Home in Stevensville
Kent Island Waterfront Home
4 beds
Apr 14 – 19
4.75 out of 5 average rating, 8 reviews
Guest favorite
Houseboat in Grasonville
Cass-Away A Luxury Houseboat
2 queen beds
Apr 26 – May 1
4.99 out of 5 average rating, 113 reviews
Guest favorite
Home in Chester
Waterfront Paradise to Work or Rest
3 beds
Apr 1 – 6
4.94 out of 5 average rating, 34 reviews
Guest favorite
Home in Chester
Kent Island Beautiful 4 BR home, central location!
8 beds
Apr 1 – 6
4.88 out of 5 average rating, 137 reviews
Guest favorite
Home in Stevensville
Kent Island Waterfront Home with Amazing Sunsets
5 beds
Apr 9 – 14
5.0 out of 5 average rating, 79 reviews
Guest favorite
Home in Stevensville
1969 Brick Rancher - Kent Island
3 beds
Apr 1 – 6
5.0 out of 5 average rating, 11 reviews
Guest favorite
Home in Chester
200+ Feet of Waterfront on 3 Acres
5 beds
Apr 3 – 8
4.93 out of 5 average rating, 15 reviews
Guest favorite
Home in Grasonville
Bay Breeze-Chester River Retreat
4 beds
Apr 3 – 8
5.0 out of 5 average rating, 19 reviews
Superhost
Home in Chester
A Shore Thing waterfront home with private pier
5 beds
Apr 1 – 6
5.0 out of 5 average rating, 6 reviews