Family-friendly holiday rentals in Windham County

My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

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

We thoroughly enjoyed our time at the cottage. It was so very peaceful and we loved being literally right around n the water! Slept amazingly well and the cottage was just lovely! Robert was also a great host. 5 stars all around and we hope to return again!

Brad was very friendly and helpful. Beautiful home!

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.

Had booked a girls getaway at Tracy and Patrick’s place and it was perfect, even with gloomy weather! The house perfectly matches all pictures and descriptions and has everything you’ll need and more for the perfect relaxing and fun getaway! We even got a cute surprise visit from their furry friends which is always loved!! There are also shops and beaches a short drive away, we just didn’t happen to go visit because we were enjoying our cozy time at the home. Thank you again Tracy and Patrick:) we would totally recommend and want to come back!

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.

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.

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!

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….

The house was very nice and comfortable for 5 adults, a child, and 2 dogs. Being able to walk down the stairs from the deck and literally be on the beach was incredible. Fantastic space, gorgeous views, and luckily the perfect weather to enjoy it all! Can't wait to rent again next year!

Cabin on Little River met our expectations and more. Myself, 2 sisters and my daughter wanted a quiet getaway. A charming open concept post and beam, pine floors and wood trim, woodstove for winter, deck with charcoal grill. It's very rural and IN the woods ( so bring bug repellant). Even though the host's home is visible you still feel tucked away. Kitchen and bath are modern and clean and the beds and livingroom were very comfortable. The soothing sound of the river is always present. It was relaxing to sit down in the adirondack chairs near its bank. The woods provide a place to walk. Lake is across the road. Glenn informed us of several events nearby that we were really interested in...but we never felt like leaving the cabin! There's a big firepit nearby and wood provided. Glenn is a wonderful host. A fellow artist, I asked to see his studio on the ground level. Even bought a couple small paintings. Do not hesitate to book this place if you are looking for a quiet respite!

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!

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!

We stayed at Monica's place multiple times when visiting my son at Wesleyan. We loved it! We appreciated the convenience of the location and ease of parking. We wish we had found it sooner because we had been staying at hotels 15-30 minuets away. The apartment is as shown and has always been clean. Its comfortable, has everything needed and is no fuss. We enjoyed inviting people over between activities on campus. Monica is very responsive and helpful and kind. She has a beautiful garden and a sweet sitting area outside for when the weather is nice!

We stayed at South Quarter House for a week with our dogs while competing in a national agility event in the area. It was a great and quiet place to stay and rejuvenate before each day’s events.

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

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!

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!

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

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.

Our family had a very nice time! Kids loved it. I definitely recommend it.

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.

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.