House holiday rentals in Windsor
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Top-rated house rentals in Windsor
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 Windsor
House rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
1–8 Apr
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Home in Montville
4.96 out of 5 average rating, 106 reviewsCasino Stay & Play House
3–10 Jun
Home in Woodstock
4.93 out of 5 average rating, 209 reviewsCedar Ridge
22–29 Jan
Home in New London
4.89 out of 5 average rating, 132 reviewsOASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
30 Jan – 6 Feb
Home in Middletown
4.95 out of 5 average rating, 19 reviewsHot Tub and pool Home away from home
31 Jul – 7 Aug
Home in Enfield
4.86 out of 5 average rating, 7 reviews3 bdrm house great neighborhood
27 Aug – 3 Sep
Home in New Hartford
4.91 out of 5 average rating, 11 reviewsMountain Serenity Lake View Pool & Hot Tub
3–10 Jan
Weekly house rentals
Home in Ware
4.89 out of 5 average rating, 112 reviewsLittle House Inn
11–18 Mar
Home in Lyme
4.97 out of 5 average rating, 190 reviews“The Answer” Tidal River-Kayaks Fire pit Fireplace
10–17 May
Home in Great Barrington
4.96 out of 5 average rating, 214 reviewsJaw dropping mountain & lake views
23–30 Apr
Home in South Windsor
4.86 out of 5 average rating, 21 reviewsGrampa Potatoes Homestead
24–31 Aug
Home in Windsor
4.87 out of 5 average rating, 23 reviewsQuiet 3 BRS home with garages
27 Aug – 3 Sep
Home in Windsor
4.8 out of 5 average rating, 5 reviewsAngel’s Guest Home . Three bedroom home/
11–18 Dec
Home in Windsor
4.97 out of 5 average rating, 36 reviewsRelax By The Water
21–28 Apr
Home in Glastonbury
4.8 out of 5 average rating, 50 reviewsIdyllic Ranch, Centrally Located
6–13 Jan
Private house rentals
Home in Springfield
5.0 out of 5 average rating, 10 reviewsQuiet 2 Bedroom - near Big E, Massmutual, Six Flag
20–27 Dec
Home in Windsor
5.0 out of 5 average rating, 10 reviewsBy The River
13–20 Aug
Home in Simsbury
4.98 out of 5 average rating, 88 reviewsNature House, water view, gazebo. 2 large decks
28 Aug – 4 Sep
Home in Bloomfield
4.94 out of 5 average rating, 88 reviewsSpacious Charming New England Cape
8–15 Nov
Home in Agawam
4.99 out of 5 average rating, 90 reviewsSunrise on the Water's Edge - Riverside Bungalow
28 Feb – 7 Mar
Home in Haddam
5.0 out of 5 average rating, 78 reviewsCozy Comforts!
14–21 Aug
Home in Bloomfield
5.0 out of 5 average rating, 14 reviewsGlobal Retreat
12–19 Jan
Home in Avon
5.0 out of 5 average rating, 29 reviewsUpdated easy living ranch-2 car garage.
13–20 Jan
Quick stats about house rentals in Windsor
Total rentals
40 properties
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.2T reviews
Destinations to explore
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