
Family-friendly holiday rentals in Windham County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Windham County
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 Windham County family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury Penthouse Minutes to Yale
My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

Villa Flora @ Norwich Inn & Spa
Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again

Hopkinton Mass 3+ Bedrooms - Great location!
Brad was very friendly and helpful. Beautiful home!

The Creation Station
Very nice place, beautiful big deck, awesome creativity to the lighting around the property. A walking path, fire pit, hot tub, big deck to relax on, and a fully equipped stage. It is a step above camping but not quite glamping. A lot of fun, and Apple is a sweet bonus hostess.

Perfect New England Getaway has a pool/ hot tub
Went with family for a weekend trip. Tracy and Patrick’s home is lovely, very beautiful and well maintained. And everyone enjoyed including my kid who found a lot of toys to play.

The Farmhouse - Hot tub eclectic farmhouse 3 br
This is our second time staying in The Farmhouse, and our 5th or 6th time booking with Ginny. This property is very relaxing, we brought our three dogs and they loved the backyard. The house was clean and organized. We enjoyed breakfast on the farmers porch. The hot tub was nice. It’s a quick drive to downtown NoHo, Florence and EastHampton. So much to do in this area. We highly recommend.

Private Luxury Waterfront Home
We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

Peaceful Spa Escape minutes to Mohegan Sun Casino
Very cute tucked away villa, with pool/hot tub, close to Mohegan Sun. The host was very responsive and the villa was clean and nicely decorated. Would love to come again :-)
Family- and pet-friendly home rentals

Boutique Hotel Special pricing available
Super close to all the fun in Newport! Parking was great and convenient! Overall a great time!!

Room with a View on Spring Pond
Linda’s place was a perfect spot to visit Watch Hill, Westerly, Stonington, and Mystic. The pond view is beautiful and Linda was so welcoming and friendly. We brought our dog who was having a bit of separation anxiety and Linda was very understanding. The apartment is lovely and private and well appointed. Highly recommend!

The Federal Suite at the Wisteria Rest
Very nice apt and perfect for a quick weekend getaway.

The Landing
Exceeded expectations can’t wait to return! Great spending time with grandkids and sharing all the local spots- Jim’s and skips dock and snug harbor diner- they are all still open from my childhood time- 70’s….

Farm Fresh Feeding Hills
We really enjoyed staying at Nancy's little farmhouse. It was perfect for us. We especially loved the back porch room where we could relax and enjoy the beautiful view as well as seeing the variety of farm animals in the backyard. The house was as mentioned in her listing and had everything we needed. I would recommend this farmhouse to anyone looking for a comfortable, relaxing place to stay. I would love to go back someday.

Rustic Retreat,unique home, minutes to Newport, RI
This home is gorgeous and filled with timeless artifacts and family heirlooms. Beautiful spots to sit outside with a morning coffee. My partner and I made a point of staying in and cooking one night because we felt right at home and wanted to appreciate the ambiance. We enjoyed the privacy and proximity to Newport very much as well. Well outside any potential chaos of downtown yet only a couple minute drive to Easton Beach. Thank you so much!

The Cottage at Indian Cove
Cute and cozy home with lovely outdoor sitting area. Woke up to the sounds of the breeze and chirping birds! You can see the water from out the kitchen windows!

Unique apartment in former art gallery.
We loved our stay! It was one of the coolest Airbnb stays our family has enjoyed. Lots of art and ambiance while also being very comfortable with all the amenities you could need. It is an open space (the bedroom walls don’t extend all the way to the ceiling), which didn’t bother us at all but something to be aware of. Thank you Pam!
Family-friendly home rentals with a pool

Casino Wine Down House
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

Pool House
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

Townhouse Close to Downtown Newport & Beaches
Absolutely beautiful space! Very comfortable and cozy! We enjoyed every bit of our visit and felt so at home. It's also in the perfect location: close enough to downtown Newport that everything is very accessible and it's also in a quiet, peaceful neighborhood for a good night's rest. But wait--there's more! Kristin was by far one of the most proactive, friendly, and helpful host I've ever experienced with Airbnb! I highly recommend this listing!

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!

Luxury Home * Pool * Fireplace
We had a very nice stay for a family wedding. Sharing the house with two combined families in January and the house was great for this. There are rooms with 3-4 beds in each so if you are looking for bedroom privacy then this house probably isn’t it. That said, we are all family so was fun to bunk up! The area is beautiful and there r a great set of trails right at the end of the road for hiking, walking cross country skiiing etc. Overall, a great stay and Kimberly was very communicative with everything

Light-bathed 3br w porch in best downtown location
My family had a wonderful stay at Susan’s place! It was very clean, well stocked, spacious, and accurately described. My toddlers especially loved playing with the toy trains. There was also a welcome bottle of wine with cheese and crackers which was so thoughtful. The location was great and only a short walk to town. We were visiting for a college reunion and will definitely look to stay here on future trips.

Private POOL, Central AC, Walk to beach, king MBR
This place was beautiful! The kitchen was spacious and accommodated our larger group nicely. Hosts left clear instructions and proactively checked in. They were even nice enough to open their pool a little earlier so we could enjoy it. Highly recommend staying here if you are planning a girls’ weekend. Bedrooms were comfy, and everyone in my group had a lovely time. Thank you!

The Classic #1 @ Ocean Beach: 6 Queen 1 Sofa Bed
Absolutely perfect. The house provides everything we needed for a great visit. Easy walk to the local beaches. Would definitely return if given the opportunity.
Destinations to explore
- Boston Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Hudson Valley Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Jersey Shore Holiday rentals
- Pocono Mountains Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Montreal Holiday rentals
- Rentals with a fireplace Windham County
- Apartment rentals Windham County
- Rentals with pools Windham County
- Rentals with lake access Windham County
- Rentals with a fire pit Windham County
- Rentals with a patio Windham County
- Rentals with a kayak Windham County
- Pet-friendly rentals Windham County
- Rentals with outdoor seating Windham County
- Rentals with breakfast Windham County
- Waterfront rentals Windham County
- Rentals with a washing machine and dryer Windham County
- House rentals Windham County
- Kid-friendly rentals Windham County
- Family-friendly rentals Connecticut
- Family-friendly rentals 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
- Charlestown Beach
- Brown University
- Foxwoods Resort Casino
- Easton Beach
- Six Flags New England
- TPC River Highlands
- Point Judith Country Club
- Ocean Beach Park
- Roger Williams Park Zoo
- Oakland Beach
- Blue Shutters Beach
- Bushnell Park
- Quotonset Beach
- Ninigret Beach
- Groton Long Point South Beach
- Groton Long Point Main Beach
- Fort Adams State Park
- Second Beach
- Goddard Memorial State Park
- Pawtucket Country Club
- Clinton Town Beach
- Mystic Seaport Museum
- Burlingame State Park
- Attawan Beach