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
14–21 Oct
Guest suite in Mansfield
4.95 out of 5 average rating, 193 reviewsCozy private apt 8 mins from UCONN - solar powered
25 Sep – 2 Oct
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
13–20 Nov
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
4–11 Oct
Home in Northampton
4.87 out of 5 average rating, 567 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
8–15 Sep
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
17–24 Dec
Cabin in Monterey
4.95 out of 5 average rating, 251 reviewsAmazing Berkshire Mountains Cabin
16–23 Sep
Villa in Norwich
4.89 out of 5 average rating, 367 reviewsPeaceful Spa Escape minutes to Mohegan Sun Casino
19–26 Sep
Family- and pet-friendly home rentals
Flat in East Haddam
4.78 out of 5 average rating, 260 reviewsThe Federal Suite at the Wisteria Rest
31 Mar – 7 Apr
Flat in Southington
4.93 out of 5 average rating, 269 reviews#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*
4–11 Aug
Flat in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
20–27 Dec
Cottage in Middlefield
4.93 out of 5 average rating, 230 reviewsLake Beseck cottage
30 Mar – 6 Apr
Flat in Northampton
4.99 out of 5 average rating, 724 reviewsNorth Street Nest, sunny downtown apartment
23–30 Apr
Loft in Essex
4.94 out of 5 average rating, 406 reviewsUnique apartment in former art gallery.
10–17 Mar
Flat in Northampton
4.95 out of 5 average rating, 220 reviewsCedar Wet Room w Soaking Tub
5–12 Mar
Flat in Middletown
4.9 out of 5 average rating, 240 reviews3 bedroom near Wesleyan, downtown
4–11 Aug
Family-friendly home rentals with a pool
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
21–28 Nov
Barn in Bethel
4.98 out of 5 average rating, 203 reviewsEscape to a Restored New England Antique Milk Barn
29 Dec – 5 Jan
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
9–16 Sep
Flat in Northampton
4.96 out of 5 average rating, 200 reviewsWood, sunshine & movies in best downtown location
2–9 Aug
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12–19 Sep
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
15–22 Oct
Home in New London
4.91 out of 5 average rating, 155 reviewsSUNSETS IN OCEAN BEACH PARK $1MIL VIEW OF ATLANTIC
6–13 Feb
Cottage in Litchfield
4.98 out of 5 average rating, 65 reviewsCottage on Litchfield Farm
22–29 Dec
Quick stats about holiday rentals that are family-friendly in Windsor
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
Total number of reviews
870 reviews
Nightly prices starting at
₹5,003 before taxes and fees
Destinations to explore
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