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
7 – 14 Dec
Bungalow in Easthampton
4.92 out of 5 average rating, 430 reviewsThe Creation Station
21 – 26 July
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
2 – 9 Apr
Home in Northampton
4.87 out of 5 average rating, 566 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
8 – 15 Sept
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
7 – 14 Dec
Cabin in Monterey
4.95 out of 5 average rating, 250 reviewsAmazing Berkshire Mountains Cabin
5 – 12 June
Villa in Norwich
4.89 out of 5 average rating, 367 reviewsPeaceful Spa Escape minutes to Mohegan Sun Casino
14 – 21 Sept
Family- and pet-friendly home rentals
Apartment in East Haddam
4.78 out of 5 average rating, 260 reviewsThe Federal Suite at the Wisteria Rest
3 – 10 Apr
Apartment in Middletown
4.9 out of 5 average rating, 240 reviews3 bedroom near Wesleyan, downtown
26 Sept – 3 Oct
Cottage in Middlefield
4.93 out of 5 average rating, 230 reviewsLake Beseck cottage
10 – 17 Dec
Apartment in Southington
4.93 out of 5 average rating, 269 reviews#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*
1 – 8 Aug
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
22 – 29 Nov
Apartment in Northampton
4.99 out of 5 average rating, 724 reviewsNorth Street Nest, sunny downtown apartment
10 – 17 Mar
Guest suite in Goshen
4.75 out of 5 average rating, 214 reviewsRural Litchfield County Apartment Goshen CT
15 – 22 Jan
Apartment in Northampton
4.95 out of 5 average rating, 220 reviewsCedar Wet Room w Soaking Tub
25 Dec – 1 Jan
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
25 Dec – 1 Jan
Apartment in Northampton
4.97 out of 5 average rating, 243 reviewsSunny Inspirit Apartment in best downtown location
17 – 24 July
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
12 – 19 Sept
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
15 – 22 Aug
Home in New London
4.91 out of 5 average rating, 155 reviewsSUNSETS IN OCEAN BEACH PARK $1MIL VIEW OF ATLANTIC
2 – 9 Sept
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
7 – 14 May
Cottage in Litchfield
4.98 out of 5 average rating, 65 reviewsCottage on Litchfield Farm
20 – 27 Dec
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
$91 AUD before taxes and fees
Destinations to explore
- New City Accommodation & holiday rentals
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