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!
Sep 27 – Oct 4
Home in Harwood
4.94 out of 5 average rating, 117 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
May 8 – 15
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec 3 – 10
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 19 – 26
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
Dec 3 – 10
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Nov 9 – 16
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
Sep 16 – 23
Home in Millington
4.91 out of 5 average rating, 34 reviewsThe Peaceful Getaway (with private pool & hot tub)
Oct 10 – 17
Weekly house rentals
Home in Shady Side
5.0 out of 5 average rating, 117 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Dec 28 – Jan 4
Home in Chestertown
4.98 out of 5 average rating, 44 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
Jun 5 – 12
Home in Chestertown
4.89 out of 5 average rating, 27 reviewsBeautifully remodeled home in Historic Chestertown
Jul 14 – 21
Home in Chestertown
4.96 out of 5 average rating, 73 reviewsCozy 3-bedroom home w/ screened in porch & firepit
Dec 5 – 12
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, 25 reviews125 High - Luxury Historical Brick Victorian
Apr 3 – 10
Home in Chestertown
5.0 out of 5 average rating, 14 reviewsNEW Chestertown Retreat
Aug 5 – 12
Home in Chestertown
5.0 out of 5 average rating, 38 reviewsWaterfront house with private dock & kayaks!
Nov 25 – Dec 2
Private house rentals
Home in Chestertown
4.94 out of 5 average rating, 31 reviewsHarbor View Haven | Waterfront w/ HOT TUB + Dock!
Jul 13 – 20
Home in Rock Hall
5.0 out of 5 average rating, 18 reviewsChesapeake Bay Retreat w/ Views!
Dec 20 – 27
Home in Chestertown
5.0 out of 5 average rating, 16 reviewsDown by the River
Dec 31 – Jan 7
Home in Greensboro
4.96 out of 5 average rating, 48 reviewsCozy 2 bedroom home on wooded private lane
Jan 4 – 11
Home in Chestertown
4.92 out of 5 average rating, 39 reviewsWknd Beach Access & Dive Bar w/ Grill & Firepit
Sep 22 – 29
Home in Chestertown
5.0 out of 5 average rating, 18 reviewsGoose Haven, new waterfront house on Fairlee Creek
Jun 17 – 24
Home in Rock Hall
5.0 out of 5 average rating, 30 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Feb 22 – Mar 1
Home in Rock Hall
5.0 out of 5 average rating, 63 reviewsIn Town, Rock Hall, Fenced-In Yard, 1 blk to Water
Jul 19 – 26
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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