Family-friendly holiday rentals in Windsor
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windsor
Guests agree: These family-friendly homes 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 family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
30 Jul – 6 Aug
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
21–26 Jul
Cottage in Ledyard
4.9 out of 5 average rating, 144 reviewsWaterfront cottage overhanging the water!
29 Jan – 5 Feb
Guest suite in Mansfield
4.95 out of 5 average rating, 193 reviewsCozy private apt 8 mins from UCONN - solar powered
14–21 Oct
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
1–8 Apr
Home in Northampton
4.87 out of 5 average rating, 566 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
8–15 Sep
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
1–8 Oct
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
20–27 Dec
Family- and pet-friendly home rentals
Apartment in Middletown
4.9 out of 5 average rating, 240 reviews3 bedroom near Wesleyan, downtown
26 Sep – 3 Oct
Guest suite in Charlton
4.86 out of 5 average rating, 380 reviewsBaker Pond Hideaway
30 Sep – 7 Oct
Farm stay in Southbridge
4.89 out of 5 average rating, 292 reviewsScandanavian Wigwam with Sauna and Forest Baths
11–16 Jun
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
12–19 Apr
Cottage in Middlefield
4.93 out of 5 average rating, 230 reviewsLake Beseck cottage
27 Mar – 3 Apr
Apartment in Northampton
4.99 out of 5 average rating, 724 reviewsNorth Street Nest, sunny downtown apartment
2–9 Apr
Apartment in Northampton
4.95 out of 5 average rating, 220 reviewsCedar Wet Room w Soaking Tub
13–20 Jan
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
8–15 Apr
Family-friendly home rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
15–22 Apr
Barn in Bethel
4.98 out of 5 average rating, 202 reviewsEscape to a Restored New England Antique Milk Barn
3–10 Sep
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
12–19 Oct
Apartment in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
17–24 Jul
Home in Woodstock
4.93 out of 5 average rating, 207 reviewsCedar Ridge
24–31 Mar
Home in Litchfield
4.93 out of 5 average rating, 162 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Apartment in Brooklyn
4.85 out of 5 average rating, 205 reviews5 Bedroom, 3.5 bath rural residence with 40' pool
26 Apr – 3 May
Home in New London
4.91 out of 5 average rating, 155 reviewsSUNSETS IN OCEAN BEACH PARK $1MIL VIEW OF ATLANTIC
2–9 Sep
Quick stats about holiday rentals that are family-friendly in Windsor
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
Total number of reviews
870 reviews
Nightly prices starting at
$101 NZD before taxes and fees
Destinations to explore
- New City Holiday rentals
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- Family-friendly rentals United States
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- Rentals with a patio Windsor
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