Skip to Main Content.
Canada
Trip Planner
List your property
Help
My trips
Sign in
It's easy to contact hosts and keep track of all your messages when you have a Vrbo account
Traveller login
Sign in as an owner
Create a free account
Feedback
Going to
Going to
Dates
Dates
Travellers
Adults
Adults
Decrease the number of adults
Increase the number of adults
Children
Ages 0 to 17
Decrease the number of children
Increase the number of children
I am travelling with pets
If checked, only properties that allow pets will be shown
Done
Search
Filters (1)
Popular (1)
Price
Rooms & spaces
Sort by recommended
36 properties
How our sort order works
Opens in a new window
Search results showing properties in Kent County, Maryland, United States of America
Google map showing 36 properties
Photo gallery for First Floor Studio Apartment in Historic Chestertown
Back Yard
Show previous image for First Floor Studio Apartment in Historic Chestertown
Show next image for First Floor Studio Apartment in Historic Chestertown
Premier Host
Apartment · 2.2 mi (3.5 km) to Chestertown center
First Floor Studio Apartment in Historic Chestertown
Sleeps 3 · 1 bedroom · 1 bathroom
9.8
9.8 out of 10
Exceptional
exceptional
60 reviews
(60 reviews)
Unavailable
More information about First Floor Studio Apartment in Historic Chestertown, opens in a new tab
Photo gallery for Historic Downtown Garden Oasis with Private Patio
Outdoor dining
Show previous image for Historic Downtown Garden Oasis with Private Patio
Show next image for Historic Downtown Garden Oasis with Private Patio
Premier Host
Apartment · 0.6 mi (1 km) to Chestertown center
Historic Downtown Garden Oasis with Private Patio
Sleeps 3 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
15 reviews
(15 reviews)
Unavailable
More information about Historic Downtown Garden Oasis with Private Patio, opens in a new tab
Photo gallery for Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Welcome to Sharp Street Apartment!
Show previous image for Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Show next image for Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Apartment · 0.2 mi (0.3 km) to Rock Hall center
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Sleeps 4 · 1 bedroom · 1 bathroom
Unavailable
More information about Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!, opens in a new tab
Apartment · 0.8 mi (1.2 km) to Chestertown center
Newly restored apartment in the heart of Chestertown
Sleeps 4 · 2 bedrooms · 1 bathroom
9.8
9.8 out of 10
Exceptional
exceptional
15 reviews
(15 reviews)
Unavailable
More information about Newly restored apartment in the heart of Chestertown, opens in a new tab
Condo · 3 min walk to Betterton Beach
BEACH WITHOUT THE BUSTLE
Sleeps 6 · 2 bedrooms · 2 bathrooms
10
10 out of 10
Exceptional
exceptional
21 reviews
(21 reviews)
Unavailable
More information about BEACH WITHOUT THE BUSTLE, opens in a new tab
Apartment · 0.2 mi (0.3 km) to Rock Hall center
Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4
Sleeps 2 · 1 bedroom · 1+ bathroom
9.8
9.8 out of 10
Exceptional
exceptional
31 reviews
(31 reviews)
Unavailable
More information about Victorian on Main Street, Rock Hall MD. Walk to everything! Sleeps 2-4, opens in a new tab
Apartment · 3.5 mi (5.7 km) to Worton center
Waterfront Retreat with Private Dock and Beach
Sleeps 4 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
2 reviews
(2 reviews)
Unavailable
More information about Waterfront Retreat with Private Dock and Beach, opens in a new tab
Apartment · 0.1 mi (0.2 km) to Rock Hall center
Knot's Landing, spacious Apt. downtown Rock Hall
Sleeps 8 · 2 bedrooms · 2 bathrooms
Unavailable
More information about Knot's Landing, spacious Apt. downtown Rock Hall, opens in a new tab
Apartment · 1.2 mi (1.9 km) to Rock Hall center
Cute waterfront apartment -- 8 min from the beach!
Sleeps 3 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
5 reviews
(5 reviews)
Unavailable
More information about Cute waterfront apartment -- 8 min from the beach!, opens in a new tab
Condo · 2 min walk to Betterton Beach
Unobstructed view of the Chesapeake Bay, w/ a beach!
Sleeps 6 · 3 bedrooms · 2 bathrooms
10
10 out of 10
Exceptional
exceptional
16 reviews
(16 reviews)
Unavailable
More information about Unobstructed view of the Chesapeake Bay, w/ a beach!, opens in a new tab
Apartment · 0.5 mi (0.8 km) to Chestertown center
Carriage House Hideaway in Middle of Chestertown
Sleeps 2 · 1 bathroom
10
10 out of 10
Exceptional
exceptional
76 reviews
(76 reviews)
Unavailable
More information about Carriage House Hideaway in Middle of Chestertown, opens in a new tab
Condo · 3 min walk to Betterton Beach
3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!
Sleeps 6 · 3 bedrooms · 2 bathrooms
10
10 out of 10
Exceptional
exceptional
1 review
(1 review)
Unavailable
More information about 3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!, opens in a new tab
Condo · 3 min walk to Betterton Beach
BEAUTIFUL BAY FRONT VIEW
Sleeps 6 · 3 bedrooms · 2 bathrooms
10
10 out of 10
Exceptional
exceptional
37 reviews
(37 reviews)
Unavailable
More information about BEAUTIFUL BAY FRONT VIEW, opens in a new tab
Apartment · 0.2 mi (0.3 km) to Rock Hall center
The Lodge on Main Street, a Victorian Apartment, walk to everything!
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.8
9.8 out of 10
Exceptional
exceptional
27 reviews
(27 reviews)
Unavailable
More information about The Lodge on Main Street, a Victorian Apartment, walk to everything!, opens in a new tab
Apartment · 10 min drive to the beach
Private Cozy Basement Apartment
Sleeps 2 · 1 bedroom · 1 bathroom
Unavailable
More information about Private Cozy Basement Apartment, opens in a new tab
Apartment · 3.6 mi (5.9 km) to Earleville center
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Sleeps 3 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
20 reviews
(20 reviews)
Unavailable
More information about WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD, opens in a new tab
Apartment · 3.2 mi (5.1 km) to Millington center
Eastern Shore Get Away
Sleeps 5 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
84 reviews
(84 reviews)
Unavailable
More information about Eastern Shore Get Away, opens in a new tab
Apartment · 0.1 mi (0.2 km) to Middletown center
Historic & Quaint Room downtown Middletown, DE awaits you!
Sleeps 2 · 1 bedroom · 1 bathroom
4.0
4.0 out of 10
1 review
(1 review)
Unavailable
More information about Historic & Quaint Room downtown Middletown, DE awaits you!, opens in a new tab
Tell us how we can improve our site
Share feedback