House vacation rentals in Chestertown
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Top-rated house rentals in Chestertown
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Chestertown house rentals
House rentals with a pool
Home in Saint Michaels
Miles Aweigh
Home in Queenstown
Bay Breeze Retreat
Home in Harwood
Luxury Home, Sleeps 15, Private Pool, Close to DC
Home in Edgewater
House in Edgewater Maryland
Home in Shady Side
Cattail Landing- Photographer's Waterfront Retreat
Home in Church Hill
Private Peaceful Waterfront House w/ Pool, Hot Tub
Home in Millington
The Peaceful Getaway (with private pool & hot tub)
Home in Chestertown
Private pier, pool at waterfront Chestertown home
Weekly house rentals
Home in Chestertown
2 Beds, 2.5 Baths, Perfect Downtown Location
Home in Chestertown
Beautifully remodeled home in Historic Chestertown
Home in Chestertown
Cozy 3-bedroom home w/ screened in porch & firepit
Home in Chestertown
Waterfront house with private dock & kayaks!
Home in Chestertown
125 High - Luxury Historical Brick Victorian
Home in Chestertown
NEW Chestertown Retreat
Home in Chestertown
Magnolia House: walk to shops, restaurants, river
Home in Bel Air
Small House on Gentleman’s Farm
Private house rentals
Home in Chestertown
River front cottage with private dock & water fun
Home in Chestertown
River Cottage, Chestertown
Home in Chestertown
Down by the River
Home in Chestertown
In Town Chestertown Rancher (1 Block to College)
Home in Rock Hall
Chesapeake Bay Retreat w/ Views!
Home in Chestertown
Beach Access, Dive Bar, Dock w/ Grill & Firepit
Home in Abingdon
AbingdonBB
Home in Rock Hall
Cozy 1920's Bungalow Near Water/Local Attractions
Quick stats about house rentals in Chestertown
Total rentals
20 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.3K reviews
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