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 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!
3–10 Apr
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
15–22 Nov
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
4–11 Apr
Home in Edgewater
4.95 out of 5 average rating, 119 reviewsHouse in Edgewater Maryland
31 Jan – 7 Feb
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
28 Mar – 4 Apr
Home in Shady Side
4.88 out of 5 average rating, 174 reviewsCattail Landing- Photographer's Waterfront Retreat
8–15 Jan
Home in Millington
4.91 out of 5 average rating, 34 reviewsThe Peaceful Getaway (with private pool & hot tub)
28 Jan – 4 Feb
Home in Rock Hall
4.91 out of 5 average rating, 23 reviewsRockfish Keeper
16–23 Oct
Weekly house rentals
Home in Lutherville-Timonium
4.93 out of 5 average rating, 131 reviews* Lovely Gem w/ Perfect Combo of Flair & Class *
19–26 Jul
Home in Chestertown
4.98 out of 5 average rating, 43 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
10–17 May
Home in Chestertown
4.96 out of 5 average rating, 72 reviewsCozy 3-bedroom home w/ screened in porch & firepit
19–26 Mar
Home in Chestertown
4.89 out of 5 average rating, 27 reviewsBeautifully remodeled home in Historic Chestertown
3–10 Aug
Home in Chestertown
5.0 out of 5 average rating, 13 reviewsNEW Chestertown Retreat
18–25 Feb
Home in Chestertown
5.0 out of 5 average rating, 24 reviews125 High - Luxury Historical Brick Victorian
30 Mar – 6 Apr
Home in Chestertown
5.0 out of 5 average rating, 37 reviewsWaterfront house with private dock & kayaks!
11–18 Jul
Home in Chestertown
5.0 out of 5 average rating, 51 reviewsLovely, Recently-Renovated Home in Chestertown
22–29 Dec
Private house rentals
Home in Rock Hall
5.0 out of 5 average rating, 18 reviewsChesapeake Bay Retreat w/ Views!
28 Sep – 5 Oct
Home in Chestertown
5.0 out of 5 average rating, 24 reviewsMagnolia House ~Historic Downtown w/Private Garden
14–21 Feb
Home in Chestertown
5.0 out of 5 average rating, 15 reviewsDown by the River
3–10 Oct
Home in Chestertown
5.0 out of 5 average rating, 17 reviewsGoose Haven, new waterfront house on Fairlee Creek
21–28 Oct
Home in Chestertown
5.0 out of 5 average rating, 23 reviewsRiver Cottage, Chestertown
15–22 May
Home in Chestertown
4.92 out of 5 average rating, 39 reviewsWknd Beach Access & Dive Bar w/ Grill & Firepit
30 Aug – 6 Sep
Home in Rock Hall
5.0 out of 5 average rating, 65 reviewsCozy 1920's Bungalow Near Water/Local Attractions
10–17 Apr
Home in Rock Hall
5.0 out of 5 average rating, 29 reviewsEastern Neck Water Paradise w/Brick oven & Beach
21–28 Oct
Quick stats about house rentals in Chestertown
Total rentals
20 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
20 properties include access to Wi-Fi
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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