House holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Chestertown
House rentals with a pool
Home in Stevensville
5.0 out of 5 average rating, 101 reviewsChesapeake Bay Waterfront ARTectural Home w/ Pool!
22–29 Aug
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
7–14 Dec
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
23–30 Nov
Home in Harwood
4.94 out of 5 average rating, 118 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
16–23 Sep
Home in Edgewater
4.95 out of 5 average rating, 120 reviewsHouse in Edgewater Maryland
19–26 Jan
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
28 Jan – 4 Feb
Home in Millington
4.91 out of 5 average rating, 34 reviewsThe Peaceful Getaway (with private pool & hot tub)
9–16 Apr
Home in Rock Hall
4.92 out of 5 average rating, 24 reviewsRockfish Keeper
17–24 Aug
Weekly house rentals
Home in Chestertown
5.0 out of 5 average rating, 14 reviewsNEW Chestertown Retreat
18–25 Mar
Home in Chestertown
5.0 out of 5 average rating, 25 reviews125 High - Luxury Historical Brick Victorian
7–14 Apr
Home in Chestertown
5.0 out of 5 average rating, 39 reviewsWaterfront house with private dock & kayaks!
25 Nov – 2 Dec
Home in Chestertown
5.0 out of 5 average rating, 51 reviewsLovely, Recently-Renovated Home in Chestertown
22–29 Dec
Home in Chestertown
5.0 out of 5 average rating, 21 reviewsIn Town Chestertown Rancher (1 Block to College)
9–16 Aug
Home in Greensboro
4.96 out of 5 average rating, 48 reviewsCozy 2 bedroom home on wooded private lane
21–28 Feb
Home in Chestertown
5.0 out of 5 average rating, 76 reviewsRiver front cottage with private dock & water fun
10–17 Dec
Home in Rock Hall
5.0 out of 5 average rating, 19 reviewsChesapeake Bay Retreat w/ Views!
13–20 Sep
Private house rentals
Home in Chestertown
5.0 out of 5 average rating, 18 reviewsGoose Haven, new waterfront house on Fairlee Creek
16–23 Jul
Home in Chestertown
4.93 out of 5 average rating, 40 reviewsWknd Beach Access & Dive Bar w/ Grill & Firepit
25 Sep – 2 Oct
Home in Rock Hall
5.0 out of 5 average rating, 67 reviewsCozy 1920's Bungalow Near Water/Local Attractions
31 Aug – 7 Sep
Home in Bel Air
5.0 out of 5 average rating, 59 reviewsSmall House on Gentleman’s Farm
2–9 Dec
Home in Millington
4.91 out of 5 average rating, 11 reviewsLark's Nest on the Chester River
3–10 Sep
Home in Rock Hall
5.0 out of 5 average rating, 30 reviewsEastern Neck Water Paradise w/Brick oven & Beach
10–17 Jan
Home in Centreville
4.86 out of 5 average rating, 14 reviewsHistoric Centreville Home
2–9 Jul
Home in Abingdon
4.95 out of 5 average rating, 63 reviewsAbingdonBB
20–27 Oct
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
1.3T reviews
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