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

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
Guest suite in Mansfield
4.96 out of 5 average rating, 207 reviews

Cozy private apt 8 mins from UCONN - solar powered

ShinjiRating, 5 stars1 month ago
The place was quiet, surrounded by beautiful woods, and truly relaxing—it was exactly what I needed. The bed was incredibly comfortable, and I slept so well each night. I also appreciated how responsive the host was to my questions via text. I would love to stay there again in the future. Thank you so much!
Top Guest favourite
Home in Colebrook
4.99 out of 5 average rating, 223 reviews

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

DaveRating, 5 stars1 month ago
We really enjoyed staying here, only wish we booked it for longer! Our son and our dog enjoyed going for walks on the trails behind the brewery. The beers and pizza from the brewery were excellent, the house is really charming and relaxing. Also got out to enjoy the disc golf course which was a fun way to spend the afternoon. I would love to come back and try out the mountain bike trails. The surrounding area was fun to explore, really can't think of any negative points to this place!
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!
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!
Superhost
Cottage in Becket
4.65 out of 5 average rating, 164 reviews

A Magical Spot on Little Robin Lake

SebastianRating, 5 stars7 months ago
Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.
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!
Top Guest favourite
Cabin in Monterey
4.95 out of 5 average rating, 281 reviews

Amazing Berkshire Mountains Cabin

StephanieRating, 5 stars3 weeks ago
We had a wonderful stay at David & Nicki’s place and especially enjoyed the cozy cabin vibes, multiple gathering spots in the house and beautiful grounds! The cabin was outfitted with everything needed for a comfortable stay. We found it to be a great base for hiking and exploring Great Barrington. Our family was delighted to use the hot tub and kayaks at the lake, as well. Highly recommend and would definitely return!

Family- and pet-friendly home rentals

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
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.
Guest favourite
Apartment in Ashfield
4.87 out of 5 average rating, 253 reviews

Zachariah House Main St. Ashfield

MaryRating, 5 stars6 days 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, 486 reviews

Flamig Farm Staycation

CharlesRating, 5 stars1 day ago
What an awesome and unique air B&B! The space is comfortable and very quiet in the evenings and night. It is well outfitted for a family and the farm was lots of fun; we discovered our little one loves chickens. Thanks for sharing a cool experience at your farm. Highly recommended.
Guest favourite
Home in Dalton
4.93 out of 5 average rating, 194 reviews

Brooksong, the perfect Berkshires getaway

JoannaRating, 5 stars3 weeks ago
Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family
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
Apartment in Northampton
4.98 out of 5 average rating, 309 reviews

Sunny Inspirit Apartment in best downtown location

LauraRating, 5 stars2 weeks ago
very nice place! we slept very well! comfortable, quiet, relaxing! we would stay there again!
Guest favourite
Apartment in Deerfield
4.93 out of 5 average rating, 60 reviews

Nestled Inn

CatherineRating, 5 stars4 weeks ago
Great stay, had everything we needed. Host was very accommodating!
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.
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.
Guest favourite
Apartment in Northampton
4.96 out of 5 average rating, 368 reviews

1880s sun-bathed beauty in best downtown location

KatieRating, 5 stars2 weeks ago
This was definitely one of the cleanest, most convenient and most responsive Airbnbs I have stayed at! Will definitely return!
Guest favourite
Home in Northampton
5 out of 5 average rating, 14 reviews

Sun-drenched 6BR Victorian steps from downtown

KevinRating, 5 stars3 weeks ago
I wish I had known about this property sooner for my visits to Amherst College. It was better than advertised. Sunny, clean, comfortable and so close to walk to town. My whole family enjoyed it very much.
Guest favourite
Home in Williamstown
4.89 out of 5 average rating, 218 reviews

Hollywood Bungalow in the Berkshires #C0191633410

JohnRating, 5 stars3 months ago
We had a great stay at the Hollywood Bungalow. House was described accurately and had so many thoughtful touches to make us feel welcome. Diana met us upon arrival and walked us around the property and the house. Such a great host! She had generously provided snacks, treats and gave a thorough overview for our stay. We were primarily focused on skiing at Jiminy Peak which was a short 20 minute drive. We also brought our 5 year-old rescue who had the best vacation of her life. She was able to use the fenced-in backyard to run around off leash and even meet a new friend when Jackson's dog visited. Diana even shoveled walking paths in the yard throughout our stay so we could get around in the high snow. The Screening Room is awesome and provided hours of entertainment. Quiet street and picturesque location. We will definitely return.

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

  • Total rentals

    20 properties

  • Nightly prices starting at

    $198 NZD before taxes and fees

  • Total number of reviews

    1K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 properties include access to Wi-Fi

  • Popular amenities

    Kitchen, Wi-Fi and Pool

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