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65 stays · 1 guest

Stays in Chester

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SUPERHOST
Entire house in Chester
Kent Island Beautiful 4 BR home, central location!
12 guests4 bedrooms8 beds2.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.83 out of 5;72 reviews
Price:$392 / night
SUPERHOST
Entire house in Chester
Shore Harbor House on Kent Island
8 guests3 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.82 out of 5;17 reviews
Price:$525 / night
Entire house in Chester
Waterfront Getaway on Cox Creek
12 guests4 bedrooms8 beds2.5 baths
WifiAir conditioningKitchenFree parking
Price:$463 / night
Entire apartment in Stevensville
Waterfront Retreat
4 guests2 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 4.62 out of 5;39 reviews
Price:$60 / night
Entire house in Queenstown
Work from Home-Nature's Paradise! Private/Peaceful
14 guests4 bedrooms9 beds2.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.48 out of 5;32 reviews
Price:$491 / night
Entire house in Chester
200+ Feet of Waterfront on 3 Acres
8 guests4 bedrooms5 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$370 / night
Entire cottage in Stevensville
Cottage on the Bay - Kent Island
8 guests4 bedrooms6 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.86 out of 5;7 reviews
Price:$396 / night
SUPERHOST
Entire apartment in Kent Narrows
Chester Riverfront At Kent Narrows
4 guests2 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;161 reviews
Price:$163 / night
SUPERHOST
Entire guesthouse in Grasonville
Eastern Shore Charm on Winchester Creek
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.89 out of 5;99 reviews
Price:$115 / night
SUPERHOST
Entire house in Stevensville
Holiday on the Bay, Kent Island Beach House
10 guests4 bedrooms6 beds2.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.94 out of 5;16 reviews
Price:$500 / night
SUPERHOST
Entire guest suite in Stevensville
Kent Island Haven - A Waterfront Getaway
2 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.97 out of 5;93 reviews
Price:$156 / night
SUPERHOST
Entire house in Stevensville
The Kent Island House
6 guests2 bedrooms4 beds3 baths
WifiAir conditioningKitchenFree parking
Rating 4.97 out of 5;29 reviews
Price:$207 / night
SUPERHOST
Entire apartment in Stevensville
Boutique by the Bay
4 guests1 bedroom1 bed1 bath
WifiAir conditioningFree parking
Rating 5.0 out of 5;74 reviews
Price:$175 / night
SUPERHOST
Entire house in Queenstown
Wye Escape
6 guests2 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.92 out of 5;12 reviews
Price:$304 / night
SUPERHOST
Entire house in Stevensville
3BR/2BT/4PK Entire House By Chesapeake Beach Club
5 guests3 bedrooms4 beds2 baths
WifiAir conditioningKitchenFree parking
Rating 4.98 out of 5;128 reviews
Price:$235 / night
SUPERHOST
Entire apartment in Grasonville
Halcyon house. Lovely views on MD eastern shore.
3 guests1 bedroom1 bed1 bath
WifiAir conditioningKitchenFree parking
Rating 4.98 out of 5;52 reviews
Price:$125 / night
Entire house in Grasonville
Serenity on the Shore
8 guests3 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
Price:$220 / night
SUPERHOST
Entire cottage in Queenstown
Wye River Cottage and Horse Barn
4 guests2 bedrooms2 beds1.5 baths
WifiAir conditioningKitchenFree parking
Rating 4.95 out of 5;37 reviews
Price:$155 / night
SUPERHOST
Boat in Stevensville
"Seafood" - The Original Caddyshack Movie Yacht
6 guests3 bedrooms5 beds3 baths
WifiAir conditioningFree parking
Rating 5.0 out of 5;15 reviews
Price:$400 / night
SUPERHOST
Entire house in Stevensville
Chesapeake Bay Home with Pool!
10 guests3 bedrooms4 beds4 baths
WifiAir conditioningKitchenFree parking
Rating 5.0 out of 5;5 reviews
Price:$750 / night
1 20 of 65 places to stay
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