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Over 1,000 places in Chester

Display total price
Includes all fees, before taxes
Home in Chester
Waterfront Farmhouse Meets Modern Luxury
6 beds
Nov 6 – 11
$569 per night
Superhost
Apartment in Chester
Cozy Waterfront Apartment Kent Island
1 queen bed
Jun 12 – 17
$106 per night, originally $138
Superhost
Home in Chester
Chester Delight- Fireplace/Deck&Patio+fenced yard
6 beds
Jul 8 – 13
$252 per night
Guesthouse in Chester
Waterfront Guest Cottage: Sunsets, Pool, Pier
6 beds
Sep 8 – 13
$474 per night
Superhost
Room in Chester
Stay with Lisa, Hosting for 7 years
Peaceful Waterfront retreat for Rest & Relaxation
Jul 22 – 27
$146 per night
Superhost
186
Reviews
4.98
Rating
7
Years hosting
Bungalow in Chester
Historic Island Home
2 beds
Jun 25 – 30
$250 per night
Superhost
Houseboat in Kent Narrows
Cass-N-Reel Luxury Houseboat
1 bed
Jun 16 – 21
$268 per night
Superhost
Home in Chester
Waterfront Getaway on Cox Creek
7 beds
Jun 19 – 25
$525 per night, originally $688
Superhost
Home in Chester
Kent Island Beautiful 4 BR home, central location!
8 beds
Jun 11 – 16
$475 per night
Superhost
Home in Chester
Bentons Pleasure- Cox Creek, Pier and Sunsets!
4 beds
Jun 11 – 17
$800 per night
Superhost
Home in Chester
Chester Getaway
3 beds
Jun 19 – 24
$246 per night, originally $273
Room in Chester
Stay with Donna
Kent Island Waterfront Suite I
Jun 11 – 16
$179 per night
Superhost
106
Reviews
5.0
Rating
2
Years hosting
Home in Chester
Kent Island Time-Waterfront
4 beds
Jun 5 – 10
$406 per night, originally $464
Superhost
Home in Chester
Kent island POOL luxury- pets welcome- sleeps 10
8 beds
Jun 8 – 13
$1,427 per night, originally $1,581
Superhost
Home in Stevensville
Cheerful & Spacious Shore Life Beauty!
2 beds
Jul 9 – 14
$225 per night
Superhost
Home in Stevensville
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
6 beds
Jun 26 – Jul 1
$299 per night, originally $379
Superhost
Room in Chester
Stay with Tony, Hosting for 5 years
Tony's place
Jun 5 – 10
$125 per night
Superhost
47
Reviews
5.0
Rating
5
Years hosting
Houseboat in Grasonville
Cass-Away A Luxury Houseboat
2 queen beds
Aug 13 – 18
$350 per night
Superhost