Family-friendly vacation 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.
Vacation 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
Bungalow in Easthampton
4.92 out of 5 average rating, 431 reviewsThe Creation Station
Jul 21 – 28
Home in Colebrook
4.99 out of 5 average rating, 203 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
Nov 9 – 16
Guest suite in Mansfield
4.95 out of 5 average rating, 193 reviewsCozy private apt 8 mins from UCONN - solar powered
Sep 19 – 26
Cottage in Ledyard
4.9 out of 5 average rating, 145 reviewsWaterfront cottage overhanging the water!
Nov 27 – Dec 4
Home in Northampton
4.87 out of 5 average rating, 567 reviewsThe Farmhouse - Hot tub eclectic farmhouse 3 br
Sep 8 – 15
Cabin in Colebrook
4.94 out of 5 average rating, 197 reviewsAdorable, storybook log cabin
Jan 24 – 31
Cabin in Becket
5.0 out of 5 average rating, 254 reviewsWaldtreff - quiet grand cabin
Dec 24 – 31
Farm stay in Kent
4.87 out of 5 average rating, 263 reviews(°) The Wandering Peacock (°)
Mar 7 – 14
Family- and pet-friendly home rentals
Guest suite in Charlton
4.86 out of 5 average rating, 381 reviewsBaker Pond Hideaway
Oct 15 – 22
Guest suite in Waterbury
4.94 out of 5 average rating, 248 reviewsPrivate 1 bedroom apartment in central Connecticut
Sep 7 – 14
Apartment in Middletown
4.9 out of 5 average rating, 240 reviews3 bedroom near Wesleyan, downtown
Aug 7 – 14
Apartment in Southington
4.93 out of 5 average rating, 269 reviews#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*
Aug 6 – 13
Apartment in Northampton
4.99 out of 5 average rating, 726 reviewsNorth Street Nest, sunny downtown apartment
Feb 17 – 24
Cottage in Middlefield
4.93 out of 5 average rating, 230 reviewsLake Beseck cottage
Apr 1 – 8
Apartment in Sandisfield
4.92 out of 5 average rating, 227 reviewsSunny Berkshire Studio Apartment
Dec 20 – 27
Home in East Haven
4.88 out of 5 average rating, 196 reviewsBeach Cottage by the Sea
Feb 14 – 21
Family-friendly home rentals with a pool
Farm stay in Rutland
4.97 out of 5 average rating, 318 reviewsFarm Living
Jan 12 – 19
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Apr 1 – 8
Barn in Bethel
4.98 out of 5 average rating, 203 reviewsEscape to a Restored New England Antique Milk Barn
Apr 17 – 24
Home in Woodstock
4.93 out of 5 average rating, 209 reviewsCedar Ridge
Jan 22 – 29
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Apartment in Northampton
4.96 out of 5 average rating, 200 reviewsWood, sunshine & movies in best downtown location
Aug 2 – 9
Home in Montville
4.91 out of 5 average rating, 234 reviewsCasino Wine Down House***
Jun 25 – Jul 2
Apartment in Brooklyn
4.85 out of 5 average rating, 205 reviews5 Bedroom, 3.5 bath rural residence with 40' pool
Apr 15 – 22
Quick stats about vacation 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
$60 before taxes and fees
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Cambridge Vacation rentals
- Montauk Vacation rentals
- New Haven Vacation rentals
- Newport Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Boston
- Family-friendly rentals The Hamptons
- Family-friendly rentals Queens
- Family-friendly rentals Connecticut
- Monthly Rentals Windsor
- Rentals with a washer and dryer Windsor
- House rentals Windsor
- Rentals with a fireplace Windsor
- Rentals with a patio Windsor
- Rentals with a fire pit Windsor
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes