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 Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
May 5 – 12
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec 6 – 13
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 22 – 29
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
Apr 13 – 20
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Oct 2 – 9
Home in Millington
4.91 out of 5 average rating, 34 reviewsThe Peaceful Getaway (with private pool & hot tub)
Nov 8 – 15
Home in Rock Hall
4.92 out of 5 average rating, 24 reviewsRockfish Keeper
Oct 13 – 20
Home in Church Hill
4.94 out of 5 average rating, 47 reviewsPrivate Peaceful Waterfront House w/ Pool, Hot Tub
Aug 29 – Sep 5
Weekly house rentals
Home in Chestertown
4.86 out of 5 average rating, 28 reviewsBeautifully remodeled home in Historic Chestertown
Jul 14 – 21
Home in Chestertown
5.0 out of 5 average rating, 14 reviewsNEW Chestertown Retreat
Jul 24 – 31
Home in Chestertown
5.0 out of 5 average rating, 25 reviews125 High - Luxury Historical Brick Victorian
Apr 5 – 12
Home in Chestertown
5.0 out of 5 average rating, 38 reviewsWaterfront house with private dock & kayaks!
Nov 25 – Dec 2
Home in Chestertown
5.0 out of 5 average rating, 51 reviewsLovely, Recently-Renovated Home in Chestertown
Dec 22 – 29
Home in Chestertown
5.0 out of 5 average rating, 21 reviewsIn Town Chestertown Rancher (1 Block to College)
Feb 8 – 15
Home in Chestertown
5.0 out of 5 average rating, 76 reviewsRiver front cottage with private dock & water fun
Dec 10 – 17
Home in Greensboro
4.96 out of 5 average rating, 48 reviewsCozy 2 bedroom home on wooded private lane
Feb 16 – 23
Private house rentals
Home in Chestertown
5.0 out of 5 average rating, 18 reviewsGoose Haven, new waterfront house on Fairlee Creek
Sep 16 – 23
Home in Chestertown
4.96 out of 5 average rating, 24 reviewsRiver Cottage, Chestertown
May 18 – 25
Home in Chestertown
4.93 out of 5 average rating, 40 reviewsWknd Beach Access & Dive Bar w/ Grill & Firepit
Sep 24 – Oct 1
Home in Rock Hall
5.0 out of 5 average rating, 66 reviewsCozy 1920's Bungalow Near Water/Local Attractions
Dec 18 – 25
Home in Rock Hall
5.0 out of 5 average rating, 30 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Feb 24 – Mar 3
Home in Bel Air
5.0 out of 5 average rating, 57 reviewsSmall House on Gentleman’s Farm
Feb 5 – 12
Home in Millington
4.91 out of 5 average rating, 11 reviewsLark's Nest on the Chester River
Dec 10 – 17
Home in Rock Hall
5.0 out of 5 average rating, 63 reviewsIn Town, Rock Hall, Fenced-In Yard, 1 blk to Water
Nov 9 – 16
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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