Skip to Main Content.
Download the app button
Download the app button with download icon
Get the app
Singapore
Trip Boards
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
Opens in a new window
Beginning of main content
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
Popular
Price
Rooms & spaces
Sort by recommended
52 properties
How our sort order works
Opens in a new window
Search results showing properties in Chestertown, Maryland, United States of America
Google map showing 52 properties
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 centre
Historic Downtown Garden Oasis with Private Patio
Sleeps 3 · 1 bedroom · 1 bathroom
10
10 out of 10
Exceptional
exceptional
14 reviews
(14 reviews)
Unavailable
More information about Historic Downtown Garden Oasis with Private Patio, opens in a new tab
Photo gallery for Carriage House Hideaway in Middle of Chestertown
Living area
Show previous image for Carriage House Hideaway in Middle of Chestertown
Show next image for Carriage House Hideaway in Middle of Chestertown
Premier Host
Apartment · 0.5 mi (0.8 km) to Chestertown centre
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
Photo gallery for Chestertown's Pet-Friendly Little Red Cottage
Exterior
Show previous image for Chestertown's Pet-Friendly Little Red Cottage
Show next image for Chestertown's Pet-Friendly Little Red Cottage
House · 0.8 mi (1.3 km) to Chestertown centre
Chestertown's Pet-Friendly Little Red Cottage
Sleeps 4 · 2 bedrooms · 1 bathroom
9.8
9.8 out of 10
Exceptional
exceptional
43 reviews
(43 reviews)
Unavailable
More information about Chestertown's Pet-Friendly Little Red Cottage, opens in a new tab
Apartment · 0.8 mi (1.2 km) to Chestertown centre
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
House · 0.7 mi (1.2 km) to Chestertown centre
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Sleeps 6 · 4 bedrooms · 2 bathrooms
10
10 out of 10
Exceptional
exceptional
59 reviews
(59 reviews)
Unavailable
More information about Circa 1900 Home in the Heart of Historic Downtown Chestertown, opens in a new tab
House · 0.7 mi (1.1 km) to Chestertown centre
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
Sleeps 8 · 3 bedrooms · 3 bathrooms
Unavailable
More information about The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown, opens in a new tab
House · 0.5 mi (0.8 km) to Chestertown centre
Country Estate in Historic District
Sleeps 10 · 5 bedrooms · 3+ bathrooms
10
10 out of 10
Exceptional
exceptional
63 reviews
(63 reviews)
Unavailable
More information about Country Estate in Historic District, opens in a new tab
House · 0.7 mi (1.1 km) to Chestertown centre
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Sleeps 14 · 6 bedrooms · 5+ bathrooms
9.8
9.8 out of 10
Exceptional
exceptional
19 reviews
(19 reviews)
Unavailable
More information about Beautiful, spacious waterfront home, an easy walk to historic Chestertown, opens in a new tab
House · 0.9 mi (1.4 km) to Chestertown centre
Historic Stepne Manor on Maryland's Eastern Shore
Sleeps 15 · 5 bedrooms · 3+ bathrooms
10
10 out of 10
Exceptional
exceptional
38 reviews
(38 reviews)
Unavailable
More information about Historic Stepne Manor on Maryland's Eastern Shore, opens in a new tab
House · 0.5 mi (0.8 km) to Chestertown centre
Victorian Hideaway: Beautiful Exterior, Modern interior
Sleeps 8 · 4 bedrooms · 2+ bathrooms
9.8
9.8 out of 10
Exceptional
exceptional
24 reviews
(24 reviews)
Unavailable
More information about Victorian Hideaway: Beautiful Exterior, Modern interior, opens in a new tab
Cottage · 0.5 mi (0.8 km) to Chestertown centre
Owl Cottage
Sleeps 4 · 2 bedrooms · 2 bathrooms
10
10 out of 10
Exceptional
exceptional
10 reviews
(10 reviews)
Unavailable
More information about Owl Cottage , opens in a new tab
House · 0.6 mi (0.9 km) to Chestertown centre
2 Beds, 2.5 Baths, Perfect Downtown Location
Sleeps 4 · 2 bedrooms · 2+ bathrooms
10
10 out of 10
Exceptional
exceptional
4 reviews
(4 reviews)
Unavailable
More information about 2 Beds, 2.5 Baths, Perfect Downtown Location, opens in a new tab
Apartment · Chestertown, 3.51 km from Chestertown
First Floor Studio Apartment in Historic Chestertown
Sleeps 3 · 1 bedroom · 1 bathroom
9.8
9.8 out of 10
Exceptional
exceptional
59 reviews
(59 reviews)
Unavailable
More information about First Floor Studio Apartment in Historic Chestertown, opens in a new tab
Apartment · Millington, 15.34 km from Chestertown
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
House · Chestertown, 14.18 km from Chestertown
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Sleeps 8 · 3 bedrooms · 3 bathrooms
10
10 out of 10
Exceptional
exceptional
256 reviews
(256 reviews)
Unavailable
More information about Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities, opens in a new tab
House · Chestertown, 3.29 km from Chestertown
Harbor View Haven | Waterfront w/ Dock + HOT TUB!
Sleeps 10 · 3 bedrooms · 2 bathrooms
10
10 out of 10
Exceptional
exceptional
8 reviews
(8 reviews)
Unavailable
More information about Harbor View Haven | Waterfront w/ Dock + HOT TUB!, opens in a new tab
House · Chestertown, 1.93 km from Chestertown
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Sleeps 6 · 3 bedrooms · 2+ bathrooms
10
10 out of 10
Exceptional
exceptional
2 reviews
(2 reviews)
Unavailable
More information about Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest , opens in a new tab
Apartment · 16.79 km from Chestertown
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
Tell us how we can improve our site
Share feedback
