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 Windsor house rentals
House rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
15–22 Apr
Home in Litchfield
4.93 out of 5 average rating, 162 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
13–20 Aug
Home in Woodstock
4.93 out of 5 average rating, 207 reviewsCedar Ridge
24–31 Mar
Home in New London
4.89 out of 5 average rating, 131 reviewsOASIS @ OCEAN BEACH PARK: 6 QUEEN BEDS
30 Jul – 6 Aug
Home in Middletown
4.95 out of 5 average rating, 19 reviewsHot Tub and pool Home away from home
15–22 May
Home in New Hartford
4.91 out of 5 average rating, 11 reviewsMountain Serenity Lake View Pool & Hot Tub
18–25 Mar
Home in Morris
4.91 out of 5 average rating, 64 reviewsLuxury Compound, Pool, Gym, Tree House, Game Barn
7–14 May
Weekly house rentals
Home in Lyme
4.97 out of 5 average rating, 189 reviews“The Answer” Tidal River-Kayaks Fire pit Fireplace
9–16 May
Home in Middletown
4.88 out of 5 average rating, 266 reviewsHistoric Greek Revival Brick Home
12–19 Oct
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
8–15 Apr
Home in Windsor
4.86 out of 5 average rating, 21 reviewsQuiet 3 BRS home with garages
17–24 Oct
Home in South Windsor
4.85 out of 5 average rating, 20 reviewsGrampa Potatoes Homestead
12–19 Sep
Home in Windsor
4.8 out of 5 average rating, 5 reviewsAngel’s Guest Home . Three bedroom home/
31 Jan – 7 Feb
Home in Windsor
4.97 out of 5 average rating, 36 reviewsRelax By The Water
12–19 Nov
Home in Glastonbury
4.8 out of 5 average rating, 49 reviewsIdyllic Ranch, Centrally Located
31 Oct – 7 Nov
Private house rentals
Home in Manchester
5.0 out of 5 average rating, 19 reviews2-BR Simplistic Retreat Minutes from Downtown
13–20 Aug
Home in Windsor
5.0 out of 5 average rating, 9 reviewsBy The River
30 Aug – 6 Sep
Home in Bloomfield
4.94 out of 5 average rating, 88 reviewsSpacious Charming New England Cape
17–24 Feb
Home in Agawam
4.99 out of 5 average rating, 89 reviewsSunrise on the Water's Edge - Riverside Bungalow
15–22 Apr
Home in Haddam
5.0 out of 5 average rating, 77 reviewsCozy Comforts!
18–25 Aug
Home in Willington
4.82 out of 5 average rating, 22 reviewsLake house step from UConn
19–26 Jul
Home in West Hartford
4.97 out of 5 average rating, 36 reviewsSprawling Classic New England Home
14–21 Apr
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
16–23 Dec
Quick stats about house rentals in Windsor
Total rentals
40 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
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
1.2K reviews
Destinations to explore
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