House vacation rentals in Chestertown
Find and book unique houses on Airbnb
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 Chestertown
5 out of 5 average rating, 21 reviewsChestertown Watson Family Farm
Home in Edgewater
4.92 out of 5 average rating, 138 reviewsHouse in Edgewater Maryland
Home in Queenstown
4.81 out of 5 average rating, 155 reviewsBay Breeze Retreat
Home in Rock Hall
4.94 out of 5 average rating, 35 reviewsRockfish Keeper
Home in Chester
4.99 out of 5 average rating, 80 reviewsWaterfront Farmhouse Meets Modern Luxury
Home in Perry Hall
4.99 out of 5 average rating, 81 reviewsGunpowder Retreat
Home in Shady Side
4.88 out of 5 average rating, 181 reviewsCattail Landing- Photographer's Waterfront Retreat
Home in Clayton
5 out of 5 average rating, 19 reviewsThe Hidden Gem•Heated pool•Pickleball Court
Weekly house rentals
Home in Chestertown
4.97 out of 5 average rating, 86 reviewsRiver front cottage with private dock & water fun
Home in Rock Hall
4.98 out of 5 average rating, 47 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Home in Chestertown
4.94 out of 5 average rating, 36 reviewsWaterfront Paradise w/ Pier - kayak to Chestertown
Home in Chestertown
4.97 out of 5 average rating, 29 reviewsRiver Cottage, Chestertown
Home in Millington
4.96 out of 5 average rating, 26 reviewsLark's Nest on the Chester River
Home in Greensboro
4.96 out of 5 average rating, 76 reviewsCozy 2 bedroom home on wooded private lane
Home in Chestertown
5 out of 5 average rating, 34 reviewsMagnolia House: walk to shops, restaurants, river
Home in Chestertown
5 out of 5 average rating, 33 reviewsIn Town Chestertown Rancher (1 Block to College)
Private house rentals
Home in Chestertown
4.96 out of 5 average rating, 24 reviewsQuiet, Shabby-chic home in downtown Chestertown
Home in Galena
4.95 out of 5 average rating, 21 reviewsConnection Pointe•River views•Quiet•Peaceful
Home in Rock Hall
5 out of 5 average rating, 26 reviews1-Particular Harbor: A Coastal Oasis!
Home in Betterton
5 out of 5 average rating, 35 reviewsRuby's Sea Glass Cottage near Betterton Beach
Home in Chestertown
4.92 out of 5 average rating, 51 reviewsEastern Shore Hideaway Deck, Kayaks, Grill, & Pit
Home in Kennedyville
4.93 out of 5 average rating, 54 reviewsComfy and Cozy on the Eastern Shore
Home in Rock Hall
5 out of 5 average rating, 90 reviewsCozy 1920's Bungalow Near Water/Local Attractions
Home in Rock Hall
4.97 out of 5 average rating, 35 reviewsEastern Shore Escape in the Heart of Rock Hall
Quick stats about house rentals in Chestertown
Total rentals
20 properties
Total number of reviews
1.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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