Family-friendly holiday rentals in Windham

The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.

Brad was very friendly and helpful. Beautiful home!

This is one of the best Air B&B experiences that we’ve had…beautiful place and surroundings, great amenities and personal touches, wonderful recommendations. Couldn’t have had a better time.

Beautiful home! Thank you for sharing it with my family. We were in town for my daughter’s college graduation. This location was perfect for my family. Cozy. Family oriented. Clean. Well equipped. Highly recommend!

Dave was an amazing host and he provided the best possible get away for our first wedding anniversary. It was private there is so much beautiful outdoor art to look at and the hot tub was the perfect way to wind down after the day. If there was a 6 star option I would give it this was everything we wanted and needed and then some

The host communicated well and was very thoughtful. The bed wasn't very comfortable and the heating unit was a bit tricky to figure out, but overall, we had a great stay.

So lovely at this awesome house right on the lake. The view is amazing, the place was spotlessly clean, and Tom and Donna are gracious hosts. I highly recommend this Airbnb, this was our second stay and we will be back. Highlights were enjoying the hot tub, a lovely sunset cruise with Tom and Donna and of course, hearing the loons on the lake at night.

We needed a nice little place to stay while we visited family and friends. This was perfect. Cute and convenient, plus lots of fun amenities like a clubhouse, ball courts, kayaks and the lake. We went off season, so the pool was closed and it was too cold to boat, but it was still fun. We enjoyed walking the community, playing ping-pong and driving the golf cart.

Wonderful getaway in the woods, but close to restaurants and shop in Rockport. We loved being greeted by the dogs and the hiking trails right outside the front door are amazing.

We instantly felt at home! Everything we needed was there, including things that I often bring with me because they aren't usually provided. Erin has set up this house the way you would if you lived there yourself--extra pillows, blankets, bathroom and kitchen towels, kitchen and laundry detergent. Basic spices, coffee and tea, sugar and creamer, every kitchen gadget and utensil. Bath products, night lights, beach chairs and towels. Even a bluetooth speaker and use of their Netflix account! All we needed were a few groceries and some sunshine to enjoy the outdoor spaces and seasonal game room. The house is spacious and charming! Their check-in and check-out methods are easy and they left ample info on how things work in the house and local restaurant and activity recommendations. This is a great location and home. I almost wish we had brought the kids...

We absolutely loved staying here! It was only an overnight trip and we wished we could have stayed longer. Very friendly hosts, lots of room, nice character within the Airbnb- the main bedroom was beautiful and both bedrooms had great views of the farm on one side and the mountains on the other. They called down the cows so we could feed them bread and it was such a fun experience! Would definitely stay here again if in the area.

Amazing host who made sure we had everything we needed for a great weekend with our toddler and dog. I would book again in a heartbeat.

Our stay in Lionsgate cabin in Cohasset was heavenly abode for a week during our stay in the last week of May. The cabin is located in peaceful surroundings with beautiful bird watching areas. The bird feeder outside our cabin kept me and my toddler daughter occupied throughout our stay here. The lawn areas and seating outside are great areas to take a stroll and listen to nature’s music. The cabin is comfortable and cozy with enough provided even for a long stay. It is located within short travel distance from many good restaurants, grocery shops and metro. Very close to the beach, we visited Nantasket and Hull many times during our stay. We loved our stay here and will stay here again. Highly recommend this cabin.

We had a great stay! The space was nice, clean, and very quiet. Parking was convenient, and the location was fantastic— since it was just a short drive the Crane Estate (where we attended a wedding). Communication with the host was great—we received quick and helpful responses. Highly recommend to anyone looking for a peaceful, well-kept place in a great area!

Nice place, clean, comfy bed, very well stocked, had everything i needed for a month. I work from home, over the internet. My only recommendation to Alan and Martha is to fix the wifi which went down multiple times per day and disconnect me from my job and conference calls. The first 3 or so times it happened, i called & texted the 2 phone numbers that Alan provided (in a note on the fridge). I also left a voice mail and knocked on their front door. but i never heard back about my text or voicemail. Eventually I unplugged are re-plugged the antenna/router which fixed the issue most times. Sometimes you have to do it 2 or 3 times, but eventually it does work.

I’ve rented several places, and this was by far the best experience I’ve had. The home was immaculate and thoughtfully stocked with everything we needed—and more! The kitchen had all the essentials, plus extras like spices, condiments, and even butter, which we needed. The bathroom was equipped with shampoo, conditioner, and body wash, making our stay even more comfortable. The mattress was high quality and very comfortable, and having access to a washer and dryer was a huge bonus. Everything was perfect—highly recommend!

We love coming here. The beach is right across the street for me to look for rocks and sea glass and then right down the road is the beach for swimming. Perfect little getaway. Rachel is an amazing hostess.

This place is simply incredible. A vintage mid century modern gem overlooking a lovely farm with mountains on the horizon. The pictures don't do it justice. The kitchen is incredibly well stocked with everything you could desire to host large family get togethers. Philip was extremely responsive and friendly throughout. My only regret is not knowing how to play the piano. We can't wait to come back in the warmer months to see the farm and garden in full effect. 10/10 recommend.

Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones

Great stay. Nice clean place. Good view of fireworks from the balcony.

It's a beautiful back yard and working farm. It's peaceful & fun to hear the animals ( peacock & donkey). There is lots to do for kids. The place was clean with roomy main bedroom & livingroom. The kitchen had everything needed but lacked ample counter space or room to store unrefrigerated food. The dehumidifier ran all the time & had to be emptied every day. The patio has couch & chairs looked comfy but got wet in rain. The picnic table was nice & coukd be dried off. My grandkids had a blast using the pool, trampoline, hammock, see-saw & climbing structures. It's a very peaceful place. We hiked on 2 different Mass Rail Trails near by.

A nice private cottage in a quiet community that was super handy for us to stay until we secured our house in New England. Everything is in place for comfortable living. We lived there for a month long and the hosts were always responsible.

Beautiful setting in the woods, incredibly peaceful- yet minutes away from a lovely New England village with shops and cafes.

Good place to stay for Hampton Beach. Short walk to the water.