Family-friendly holiday rentals in Windham County

Find and book unique family-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Windham County family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Apartment in New Haven
4.75 out of 5 average rating, 141 reviews

Luxury Penthouse Minutes to Yale

AbiolaRating, 5 stars3 weeks ago
My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.
Superhost
Condo in Norwich
4.84 out of 5 average rating, 151 reviews

Villa Flora @ Norwich Inn & Spa

ChristianRating, 5 stars4 weeks ago
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
Guest favourite
Home in Hopkinton
4.95 out of 5 average rating, 155 reviews

Hopkinton Mass 3+ Bedrooms - Great location!

DeanneRating, 5 starstoday
Brad was very friendly and helpful. Beautiful home!
Guest favourite
Bungalow in Easthampton
4.92 out of 5 average rating, 504 reviews

The Creation Station

KennyRating, 5 stars1 month ago
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.
Top Guest favourite
Home in Stonington
4.97 out of 5 average rating, 227 reviews

Perfect New England Getaway has a pool/ hot tub

ApoorvRating, 5 stars1 day ago
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.
Superhost
Home in Northampton
4.88 out of 5 average rating, 638 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

AngieRating, 5 stars1 month ago
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.
Superhost
Villa in Guilford
4.91 out of 5 average rating, 11 reviews

Private Luxury Waterfront Home

VirginiaRating, 5 stars22 months ago
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.
Guest favourite
Villa in Norwich
4.89 out of 5 average rating, 403 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

MalloryRating, 5 stars1 week ago
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

Guest favourite
Condo in Newport
4.92 out of 5 average rating, 688 reviews

Boutique Hotel Special pricing available

AlyssaRating, 5 stars1 day ago
Super close to all the fun in Newport! Parking was great and convenient! Overall a great time!!
Top Guest favourite
Guest suite in Westerly
4.97 out of 5 average rating, 143 reviews

Room with a View on Spring Pond

RosieRating, 5 stars1 day ago
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!
Superhost
Apartment in East Haddam
4.79 out of 5 average rating, 284 reviews

The Federal Suite at the Wisteria Rest

DanRating, 5 stars1 month ago
Very nice apt and perfect for a quick weekend getaway.
Top Guest favourite
Home in Narragansett
4.96 out of 5 average rating, 135 reviews

The Landing

Melissa or MissyRating, 5 stars2 weeks ago
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….
Guest favourite
Home in Feeding Hills
4.89 out of 5 average rating, 976 reviews

Farm Fresh Feeding Hills

AndreaRating, 5 stars5 days ago
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.
Guest favourite
Home in Middletown
4.96 out of 5 average rating, 280 reviews

Rustic Retreat,unique home, minutes to Newport, RI

JamesRating, 5 stars1 week ago
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!
Top Guest favourite
Cottage in Guilford
4.94 out of 5 average rating, 268 reviews

The Cottage at Indian Cove

ChristineRating, 5 stars1 week ago
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!
Guest favourite
Loft in Essex
4.94 out of 5 average rating, 442 reviews

Unique apartment in former art gallery.

JenniferRating, 5 stars2 weeks ago
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

Guest favourite
Home in Montville
4.92 out of 5 average rating, 273 reviews

Casino Wine Down House

EsperanzaRating, 5 stars6 days ago
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
Top Guest favourite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars3 weeks ago
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!
Superhost
Townhouse in Middletown
4.97 out of 5 average rating, 35 reviews

Townhouse Close to Downtown Newport & Beaches

LydiaRating, 5 stars1 day ago
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!
Superhost
Condo in Farmington
4.81 out of 5 average rating, 53 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

DenisRating, 5 stars6 months ago
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!
Guest favourite
Home in Brimfield
4.88 out of 5 average rating, 73 reviews

Luxury Home * Pool * Fireplace

DanaRating, 5 stars4 months ago
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
Guest favourite
Apartment in Northampton
4.94 out of 5 average rating, 224 reviews

Light-bathed 3br w porch in best downtown location

RachelRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Middletown
4.92 out of 5 average rating, 63 reviews

Private POOL, Central AC, Walk to beach, king MBR

MarciRating, 5 stars1 month ago
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!
Guest favourite
Home in New London
4.85 out of 5 average rating, 172 reviews

The Classic #1 @ Ocean Beach: 6 Queen 1 Sofa Bed

ChristopherRating, 5 stars3 weeks ago
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