Family-friendly holiday rentals in Easthampton

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Easthampton family-friendly rentals

Family-friendly home rentals with a hot tub

Home in Lenox
4.74 out of 5 average rating, 77 reviews

Luxury Fox Hollow Home-Laurel Lake

TonyaRating, 5 stars1 week ago
Beautiful location. Perfect yard to sunbathe and enjoy the scenery in the mornings and evenings. Enjoyed all the amenities such as the hot tub and pool table with my group. The house was a perfect fit for my group of 7 + a dalmatian, there would have been room for 1-2 more people before it felt too tight. Didn’t have any trouble with cooking a steak and veggie dinner at this location, there were enough tools for us. Would recommend bringing your own spices and seasonings though as the spice cabinet was only stocked with salt, pepper, and a couple sprinklings of other basic things. The instructions to get to the house were a bit unclear and hard to follow after a long road trip up. Eventually found the house and was pleasantly surprised. The photos don’t do it justice! Definitely a hidden gem and would go back again!
Home in Pittsfield
4.81 out of 5 average rating, 182 reviews

Beautiful House By The Lake W/Jetted Hot Tub

AndrewRating, 5 stars2 months ago
Our stay was excellent. House was exactly as advertised and fit our needs perfectly. We were a large group including young children and everyone had plenty of space both for sleeping and recreation. Kitchen was well stocked with anything you needed to cook your meals. Host was responsive and very clear with instructions and answering questions. 5/5 stars. Would highly recommend. A quick note for future guests. If the weather is cold the kitchen floor gets cold. Would recommend packing slippers.
Superhost
Home in Lee
4.96 out of 5 average rating, 78 reviews

Spectacular Berkshire Retreat on Private Lake

SharonRating, 5 stars6 months ago
Our family (and dog) stayed for Thanksgiving weekend and we had an amazing time. There is a gorgeous 0.8 mile walk in the woods right from the back of the house. We loved the hot tub! And we made fires in the fireplace every day. The kitchen was well appointed and we were easily able to cook our Thanksgiving dinner. We were close to Great Barrington, Lenox, and Stockbridge. Great food. Great shopping. Guidos in Pittsfield was great for food shopping. The house and setting were perfect. We will definitely be back!
Top guest favourite
Home in Colrain
4.94 out of 5 average rating, 178 reviews

Secluded Farmhouse Retreat - stunning views

HerinRating, 5 stars1 month ago
Mark's High Pocket Bed and Barn was absolutely stunning and cozy. My friends and I stayed while attending a wedding nearby, and were so delighted by the home the minute we walked in. Thoughtful furniture and decoration through out the house, as well as beautiful yard and walking paths that were so nice to explore on a sunny spring day. The home was immaculately clean and well stocked. Mark was very communicative and responsive. We would all very happily stay at this home again!
Guest favourite
Home in Hadley
4.94 out of 5 average rating, 62 reviews

Large Family Home Near Five Colleges

AnnieRating, 5 stars2 weeks ago
Justin's house was perfect for our needs - a large family gathering for a memorial service. We loved being able to be together in one house with plenty of room and beds for everyone. We didn't use the outdoor space much but it was nice to have, and Justin was very generous with his instructions to use whatever we found. The house was clean and except for a few little issues that he warned us about (leaky freezer, wonky dishwasher), it was perfect!
Top guest favourite
Home in Chester
4.97 out of 5 average rating, 351 reviews

Riverfront Getaway

PeterRating, 5 stars3 months ago
Second time staying here, and we continue to love it! The location is great: pretty much anything in western Mass can be reached within about an hour or less from the house. At the house itself, you have a clean, comfortable, and ample space. The hot tub overlooking the river is definitely a highlight. The sounds of the river and the occasional rumble of trains passing by create a beautiful atmosphere. Highly recommended!
Top guest favourite
Home in Colebrook
4.99 out of 5 average rating, 224 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

MichaelRating, 5 stars1 month ago
Really nothing negative to say. We appreciate all extra personal touch the hosts left for us. I wish all ABNB locations had the same care and attention to detail for their guests.
Top guest favourite
Home in Goshen
4.91 out of 5 average rating, 69 reviews

Charming farmhouse retreat with post-hike hot-tub

EricaRating, 5 stars1 month ago
This is our second time renting this house and working with Anna and Victoria. They are wonderful and kind hosts and so easy to work with. The entire home was very clean and spotless. We ABSOLUTELY loved our stay and had the perfect girls weekend. The farmhouse is so unique, vintage and spacious. The bathrooms are a women’s dream with the fun designs, lighting and the fun floor tiles. Although we are from Connecticut, we love visiting the Goshen/Litchfield area to get a change of scenery, visit the local winery’s and vineyards in the area and check out downtown Litchfield for lovely dinners and cocktail hours. The book case collection also intrigued us every morning when we were sipping our coffee and looking out the back porch area. We enjoyed the fact that there were tons of board games which we played at least one every night during our stay. We will definitely be booking our next visit and be back to this gorgeous home!

Family- and pet-friendly home rentals

Guest favourite
Home in Feeding Hills
4.89 out of 5 average rating, 977 reviews

Farm Fresh Feeding Hills

KaitlynRating, 5 stars5 days ago
A lovely place to stay. Beautiful view of the animals and mountains. Host was nice and accommodating.
Guest favourite
Loft in Northampton
4.97 out of 5 average rating, 273 reviews

Light-filled Studio Apt. Near Smith

CarrieRating, 5 stars1 week ago
A great stay! The space was exactly as described and Carol and Robin were terrific hosts. East checkin and out and we loved the tea, milk and yogurt + homemade granola! It was very comfortable and cozy, surrounded by loads of books.
Top guest favourite
Home in New Salem
4.9 out of 5 average rating, 220 reviews

Stone n' Sky Lodge

RobertRating, 5 stars2 weeks ago
We needed a place for our family - 3 couples and 2 young children - to stay for the wedding of our daughter. Sarah's house was great. It had plenty of room for the kids to play inside as it rained a good part of our visit. (Fortunately the rain held off for the wedding.) Sarah provided eggs fresh from her chickens - they were delicious. She also gave us information about local restaurants. We saw wild turkeys walking outside the house. All in all a delightful stay.
Guest favourite
Flat in Ashfield
4.87 out of 5 average rating, 253 reviews

Zachariah House Main St. Ashfield

MaryRating, 5 stars1 week ago
We Minnesotans felt like we had a true New England experience during our delightful stay at Zachariah House! The decor made us feel like we had dropped into another century, yet we had all the modern conveniences, including cozy beds and delicious coffee. It was perfect for grandparents, parents, and baby.
Superhost
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars6 months ago
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Top guest favourite
Farm stay in West Simsbury
4.96 out of 5 average rating, 487 reviews

Flamig Farm Staycation

CassandraRating, 5 stars1 week ago
I almost didn’t want to write a review so people don’t book this place…. But I definitely have to. It was such a blast. We collected eggs in the morning, we tried peacock eggs for breakfast. They had an amazing playground, and awesome cats and dogs running around the farm. The fact that we got the farm to ourselves after hours was so memorable. My first airbnb and probably will put other airbnbs expectations high.
Top guest favourite
Home in Russell
4.96 out of 5 average rating, 265 reviews

South Quarter House

SheilahRating, 5 stars2 weeks ago
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.
Top guest favourite
Chalet in Peru
4.92 out of 5 average rating, 287 reviews

Swiss Chalet Style Timberframe Home in Berkshires

WilliamRating, 5 stars3 weeks ago
I had a wonderful stay at Laura’s place. The home is not only beautiful but thoughtfully constructed. Its exposed wood frame feels so natural and adds to the calming atmosphere. The backyard was clean, maintained, and offered a serene space to relax. Laura’s instructions were clear and made finding and settling into the house easy. The bedrooms and bathrooms were incredibly cozy and well-kept. Every detail made the space feel warm and welcoming. It’s also a fantastic spot for groups. Our group of six friends fit very comfortably, with plenty of space to relax and unwind. I’d absolutely recommend this home to anyone looking for a peaceful, comfortable getaway.

Family-friendly home rentals with a pool

Top guest favourite
Guest suite in Mansfield
4.96 out of 5 average rating, 208 reviews

Cozy private apt 8 mins from UCONN - solar powered

BillRating, 5 stars3 weeks ago
We have been staying here over the last 4 years, when we visit UConn, and will miss it now that our daughter has graduated. Keri is wonderful host, welcoming & accommodating. Her home in the woods is a refuge, comfortable, peaceful, and minutes from campus.
Guest favourite
Home in Hancock
4.88 out of 5 average rating, 49 reviews

Jiminy Peak Peaceful Home in Berkshires

EllenRating, 5 stars4 months ago
We had a great stay at Michelle’s place. It was very conveniently located to the base of Jiminy Peak, which made getting to and from the mountain very easy. The house was very well appointed and had everything we needed. We used the fireplace twice and it was super easy. Having access to the facilities at The Country Inn at Jiminy Peak was great as I am injured and can’t ski currently, so instead I went to the gym each day. My family didn’t want to leave and my kids are asking when we can go back!
Guest favourite
Flat in Deerfield
4.93 out of 5 average rating, 60 reviews

Nestled Inn

CatherineRating, 5 stars1 month ago
Great stay, had everything we needed. Host was very accommodating!
Top guest favourite
Home in Pittsfield
4.96 out of 5 average rating, 57 reviews

Berkshire Lakefront Home W/Pool-100%Renovated

Lesley-AnneRating, 5 stars3 weeks ago
Our group of 10 family members and close friends had a wonderful time at this lovely house. It's large, clean, comfortable, and well equipped for cooking and relaxing together. The instructions were clear and comprehensive. Jay is friendly, knowledgeable, and responsive - in short, an excellent host. Our whole experience gets a big thumbs up!
Guest favourite
Home in Ashford
4.87 out of 5 average rating, 78 reviews

Large secluded house in the Woods; Pool, hot tub!

TalRating, 5 stars9 months ago
We came as a group of friends with a baby to stay at Blake and Tracy's house, and we had a great stay. They were very communicative and accommodated all our requests to ensure our stay was excellent. They asked in advance if it would be okay for their child to stay in his room inside the house, and we agreed. We didn’t see him at all during our stay, and it didn’t disturb us in the slightest. The fact that Blake and Tracy live right next door was convenient, as they were readily available for anything we needed, but we never felt their presence. We will definitely come back!
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
Hotel room in Hancock
4.87 out of 5 average rating, 15 reviews

Wyndham Bentley Brook ** 2BR Deluxe

KateRating, 5 stars3 months ago
This was a great place to stay as a family for a ski trip! Easy ski on/ski off access to the mountain with ski lockers was a huge plus. Easy enough to walk to a few restaurants. The kids love the movie theater, pool and game room. Very clean and friendly/helpful staff at front desk.
Townhouse in Lee
4.67 out of 5 average rating, 18 reviews

Beautiful 2BD Villa in Berkshires Resort

Neil And KathyRating, 5 stars69 months ago
If you come to the Berkshires, this is a clean, comfortable, spacious place for two couples, with nice resort amenities. The kitchen is minimally equipped, but adequate for preparing simple meals.

Quick stats about holiday rentals that are family-friendly in Easthampton

  • Total rentals

    20 properties

  • Nightly prices starting at

    $154 SGD before taxes and fees

  • Total number of reviews

    1K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

Destinations to explore