Family-friendly vacation rentals in Pioneer Valley

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Pioneer Valley family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A tranquil lake reflects a charming red house set against a backdrop of lush green trees and blue sky. The surrounding nature provides a serene atmosphere, inviting peaceful contemplation and relaxation.
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 favorite
A charming red farmhouse is set against a backdrop of rolling hills and blue skies. The property includes a separate red building nearby, surrounded by lush green grass and a landscaped stone garden featuring colorful flowers and greenery.
Home in Colrain
4.94 out of 5 average rating, 179 reviews

Secluded Farmhouse Retreat - stunning views

ColinRating, 5 stars2 weeks ago
We were four retired couples. Worldly travelers used to very comfortable surroundings. No TV was fine for this occasion. The farmhouse is designed with furniture comfortable for all, appointed in a farmhouse motif, of course, but the design aesthetic is of a quality respectful of its guests. "Good enough", never is. Obviously, the quality of consideration our Host has for the farmhouse presentation is treat your guest with respect and it will be reciprocated. One of the individuals commented, prior to even unpacking: "Perfect Place!" While it rained, we did not have the opportunity to enjoy the firepit, but some enjoyed the Hot Tub, as we all talked late into the night. This is located "close enough", 10 min drive to "civilization", to sites and shopping but it's really a more slightly secluded, private environment whereby a large family or, like us, distinct families can share comfortably, "come and go" separately together or stay together, together. We enjoyed ourselves.
Guest favorite
The exterior of the home features a classic design with a large front porch and expansive lawn. Surrounded by mature trees, the property showcases a blend of natural beauty and inviting architecture under a clear blue sky.
Home in Hadley
4.94 out of 5 average rating, 62 reviews

Large Family Home Near Five Colleges

AnnieRating, 5 stars3 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 favorite
The spacious A-frame home is set against a backdrop of vibrant trees and lush greenery. A well-manicured hill leads to the house, which features large windows allowing natural light to fill the interior. The bright blue sky complements the tranquil outdoor scenery.
Chalet in Dover
4.97 out of 5 average rating, 113 reviews

Grey Wolf's Den: 5 miles to Mount Snow w/HOT TUB

CaterinaRating, 5 stars3 months ago
Great location! This was a two family trip up to Mt Snow. We had a wide range of ages and 2 dogs. The house had plenty of toys and things for the kids to do - their favorite was the scavenger hunt! The kitchen is one of the best stocked kitchens compared to other Airbnbs we have used. The beds were comfortable - plenty of extra pillows and blankets. The couch and chairs in the living area were also very comfortable. The hot tub was very nice and enjoyable after everyone went skiing.
Superhost
A charming farmhouse is depicted, featuring a white exterior and a welcoming red front door. Windows provide natural light, and a wood pile is neatly stacked beside the entrance. Lush greenery and seasonal foliage surround the home, set against a clear blue sky.
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.
Top guest favorite
An open-concept kitchen features a central island with bar seating for two, surrounded by wooden cabinetry and ample natural light from large windows. A dining area with a table for six is visible, complemented by wooden chairs and a cozy living space in the background, showcasing a comfortable setting.
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars3 months ago
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.
Top guest favorite
A cozy living room features a brown sofa positioned centrally, paired with an ottoman. Striped armchairs flank the space, with two lamps providing soft illumination. Warm wood paneling and large windows contribute to a welcoming ambiance, complemented by a decorative area rug underneath.
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.
Guest favorite
Home in Dover
4.97 out of 5 average rating, 93 reviews

Wonderful House! Rec Room HotTub Firepit Garden!

KevinRating, 5 stars3 months ago
Celine’s place was great! Plenty of room for our party of 4. We felt right at home with all the amenities at the property. The kitchen was fully stocked with everything you’d need to cook but we opted to go out for dinner during our stay. We’ll def book again when in the area.

Family- and pet-friendly home rentals

Guest favorite
A circular stone entryway frames a winding path leading to a quaint cabin nestled among tall trees. Sunlight filters through the forest canopy, casting a gentle glow on the surrounding greenery.
Guesthouse in Lenox
4.93 out of 5 average rating, 105 reviews

The East Street Cabin

PeterRating, 5 stars8 months ago
We were in Lenox to attend a reunion for the Lenox School for Boys ( Grad “66” ). The cabin was perfect for our needs especially because we could have our dog with us. Most of our time was spent with activities scheduled for the reunion so we didn’t really get to enjoy the peaceful atmosphere surrounding the cabin. There will be another reunion in 2026 so we will be looking forward to another stay at the Luv Shack. Thanks for sharing your abode. Pete & Becky Davis Mechanicsburg PA
Top guest favorite
A serene pond reflects the cloudy sky, surrounded by lush greenery and tall grasses. The still water enhances the tranquil atmosphere of the landscape, with distant buildings nestled among the trees, completing the rural setting.
Guesthouse in Stephentown
5 out of 5 average rating, 416 reviews

Dog Friendly Studio

LilyRating, 5 stars3 weeks ago
We absolutely loved Maple Hill Farms. It's a wonderful place and a perfect choice for a trip to the Berkshires if you're an animal lover. The best part of our weekend was bonding with Philip's sweet and friendly donkeys! The studio is well laid out with everything you need, the farm is beautiful and peaceful (except for the roosters, haha!), and the location is great for visiting local sights like Mass MoCA and The Mount. We hope to be back!
Guest favorite
A charming exterior is visible with a well-maintained pathway leading to a covered porch. The porch features colorful seating options, and greenery surrounds the area, including shrubs and small trees. A flag hangs proudly from the porch, while a mailbox is positioned near the driveway.
Loft in Wilmington
4.91 out of 5 average rating, 202 reviews

Walk to Village/Lake Whitingham

JuliannRating, 5 stars4 weeks ago
Great little studio apartment attached to Emily’s house, very peaceful yet walkable to downtown Wilmington!!! Easy to get to the Hoot and Toot trail, and about a mile from the boat launch/picnic grove at the lake!! Absolutely would recommend and stay again!!
Guest favorite
The entrance to the private suite features a wooden deck leading to a purple door. Large windows on either side allow natural light to illuminate the entryway. Surrounding greenery and a gravel pathway create a welcoming approach to the suite.
Home in Feeding Hills
4.89 out of 5 average rating, 977 reviews

Farm Fresh Feeding Hills

KaitlynRating, 5 stars1 week ago
A lovely place to stay. Beautiful view of the animals and mountains. Host was nice and accommodating.
Top guest favorite
Barn in Guilford
4.99 out of 5 average rating, 126 reviews

The Carriage Barn

AristidesRating, 5 stars3 weeks ago
We really enjoyed our stay here. The place is incredible, you’ll have everything you’d need. Full of very thoughtful details. Very cozy, confortable and charming. The surroundings are beautiful and in a short drive you’d find anything you may need in Brattleboro. From dining to great coffee, groceries and more… I loved how simple and easy where the instructions for check-in and Out. Katherine was very friendly and responsive. Would definitely stay there again.
Guest favorite
A calming room features a spacious bed covered in soft linens beneath a skylight. A wooden bookshelf filled with books sits against the wall. Two lamps provide ambient light, while a cozy chair and a low coffee table complete the inviting space.
Loft in Northampton
4.97 out of 5 average rating, 273 reviews

Light-filled Studio Apt. Near Smith

CarrieRating, 5 stars2 weeks 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 favorite
A view from above displays a cozy sitting area beneath exposed wooden beams. A rich, patterned rug covers the floor, while a plush armchair and a small table are positioned nearby. Natural light filters in through the adjacent windows, illuminating bookshelves filled with items.
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.
Top guest favorite
A quaint colonial home is surrounded by lush greenery, with a vibrant rainbow arcing across the sky in the background. The well-maintained garden features blooming daffodils, and the soft grass invites relaxation and exploration.
Apartment in Newfane
4.97 out of 5 average rating, 455 reviews

Rock River Retreat: VT Oasis Pet Friendly

Kate-LynnRating, 5 stars2 weeks ago
It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.

Family-friendly home rentals with a pool

Top guest favorite
A cozy bedroom features a bed dressed in a floral comforter with a decorative pillow. A soft glow from a floor lamp illuminates the space, complemented by a window that offers natural light. A mini-fridge is present in the corner, adding convenience.
Guest suite in Mansfield
4.96 out of 5 average rating, 208 reviews

Cozy private apt 8 mins from UCONN - solar powered

BillRating, 5 stars1 month 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 favorite
An outdoor heated pool is surrounded by a stone patio, furnished with lounge chairs and umbrellas. Lush green grass and neatly trimmed shrubs outline the pool area, complemented by trees and well-maintained landscaping in the background.
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

Bear's Den - Mt Snow Townhome w/ Heated Pool!

NikkiRating, 5 stars4 months ago
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.
Guest favorite
A sunny outdoor area features a clear swimming pool surrounded by a well-maintained patio. Lounge chairs and umbrellas are arranged near the pool, while a tranquil pond and lush greenery form the serene backdrop.
Home in West Dover
5 out of 5 average rating, 45 reviews

The Manor-Stunning Modern Farmhouse with Hot Tub

SarafRating, 5 stars6 months ago
Amazing experience! Everything was prepared and fully equipped for us, from towels, soaps and shampoos, even spices and oil in the kitchen! Definitely recommended, and we will be happy to visit there again! summer or winter!
Guest favorite
A clear blue pool is surrounded by a sunbathing area featuring white lounge chairs. Lush greenery and trees are visible in the background, providing a natural setting. A fenced area with tall trees enhances the outdoor space for relaxation.
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars2 months ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favorite
A circular pool is set within a grassy area, surrounded by lush greenery. A shaded picnic area features a large table beneath a white umbrella. Colorful inflatables are visible on the water's surface, adding a playful touch to the serene outdoor setting.
Bungalow in Easthampton
4.92 out of 5 average rating, 505 reviews

The Creation Station

ErinRating, 5 stars2 weeks ago
John went out of his way to ensure we had a great stay. It was a great place that accommodates many and the hot tub was relaxing after a long day of golf.
Top guest favorite
The living room is furnished with a blue sofa and a light armchair, complemented by wooden side tables and lamps. A coffee table is positioned centrally on a carpeted floor. Walls are adorned with wood paneling and artwork, enhancing the space's rustic charm.
Townhouse in Dover
4.94 out of 5 average rating, 81 reviews

Cozy Bear- 1 mile to Mt Snow Ski Home

KimberlyRating, 5 stars1 month ago
We really loved staying here. The location was perfect and the accommodations were fantastic. Our host was exceptional in making sure we were comfortable and informed. We will definitely try to book again.
Superhost
The spacious room features a king bed with crisp linens, complemented by two bedside lamps. A cozy sitting area includes a wingback chair and a small table. Natural light floods the space through large windows, and warm wood flooring enhances the inviting atmosphere.
Cottage in Dover
5 out of 5 average rating, 14 reviews

Luxury King, fireplace, pvt entrance- Farmhouse 1

JeannieRating, 5 stars26 months ago
Wonderful stay at Farm Road Estate! Clean, private, with a peaceful vibe and gorgeous area. The room itself was amazing and spacious, and lighting the fireplace at night in our room was an added bonus. The bar/restaurant on the grounds wasn’t open when we stayed, so looking forward to staying here again when it is open! Definitely need a car to travel and explore the town/surrounding towns. There are some good restaurants and bars within a less than 10 minute drive! 5/5 stars!
Guest favorite
A serene swimming pool is surrounded by tall greenery, offering a tranquil escape. The crystal-clear water reflects sunlight, inviting relaxation. A decorative statue is visible in the background, enhancing the peaceful atmosphere of the outdoor space.
Apartment in Northampton
4.96 out of 5 average rating, 371 reviews

1880s sun-bathed beauty in best downtown location

EmilyRating, 5 stars2 weeks ago
I got a great last minute deal on this place and am so so happy I stayed here! Fantastic location and truly such a lovely space. Felt right at home when I found our welcome gift of a bottle of wine, some cheese and crackers upon arrival! Thank you for having us Susan, we loved your home!

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