Family-friendly vacation rentals in Hampshire County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Hampshire County family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
A comfortable living area is displayed with a large television mounted on a wooden console. A light-colored cabinet holds decor items, while green plants add a touch of nature. Soft seating in neutral tones provides a welcoming space for relaxation.
Home in Chester
4.97 out of 5 average rating, 351 reviews

Riverfront Getaway

PeterRating, 5 stars1 month 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!
Guest favorite
Home in Hadley
4.93 out of 5 average rating, 61 reviews

Large Family Home Near Five Colleges

SusanRating, 5 stars6 months ago
I give this place 10/10. The house was amazing! It was immaculate and soo well stocked. The kitchen was free of any clutter but had everything we needed. The host was unbelievably responsive w/ anything we asked. We can’t wait to go back!
Superhost
Home in Northampton
4.88 out of 5 average rating, 632 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

KatherineRating, 5 stars2 weeks ago
A peaceful location with chill activities for all ages...we enjoyed the phonograph, the retro Atari, the hot tub, the window bird feeder, and watching birds in the spacious yard and conservation area. Herons, hawks, and songbirds viewed. The hot tub was sparkling clean, and the linen robes were a thoughtful touch. Wifi worked great. We arrived late but instructions for entry were crystal clear. Virginia answered my questions promptly and warmly. Definitely a winner.
Guest favorite
An 8-person hot tub bubbles gently under the night sky, surrounded by trees. A scenic trail, lined with colorful lights, winds through the woods leading toward a well-lit deck. The inviting ambiance is set for relaxation and exploration.
Bungalow in Easthampton
4.92 out of 5 average rating, 495 reviews

The Creation Station

SpencerRating, 5 stars2 weeks ago
We love the creation station! We stayed for one night and it simply wasn’t enough! What a cool and magical property. Inside is quite a trip. Surround sound for your listening pleasure, huge projection screen for watching tv. Comfortable beds, and the place was well kept up and clean. Outside is magical at night and the hot tub was just perfect after a long day. John was super nice and very helpful. We will certainly be back for some more fun. Highly recommend this place you will not be disappointed. Peace & Love: Spencer and Julie

Family- and pet-friendly home rentals

Guest favorite
A cozy living space is highlighted by a striped sofa and an olive green armchair. A marble-topped coffee table sits centrally, while large windows frame a snowy outdoor scene. A bookshelf filled with magazines adds a touch of warmth and invitation.
Home in Becket
5 out of 5 average rating, 29 reviews

Escape To The Berkshires!

LauraRating, 5 stars4 months ago
Escape to the Bershires is a true gem. We fell in love with the house and the location. The house is very spacious, we enjoyed the living room with the excellent entertainment center, the 2 other gathering rooms were great for private conversations. Each bedroom was comfortable and nicely decorated. The kitchen is large and well stocked with everything you would need to make your gourmet meals. I have been renting from Airbnb for 8 yrs and this home is by far our favorite. We will return.
Guest favorite
The serene lake is framed by lush greenery, with calm waters reflecting the clear blue sky. A small sandy area leads to the water's edge, where a dock can be seen anchored nearby. The tranquility of the setting is evident, inviting relaxation and exploration.
Cottage in Becket
4.78 out of 5 average rating, 163 reviews

Tranquil Lake Cottage on 3 Acres with Large Deck

SarahRating, 5 stars1 week ago
We had a wonderful long weekend at Michelle’s place. We woke to 8 inches of snow in April, so made good use of the fireplace. We enjoyed exploring the area, found several fun places to ride our mountain bikes and showed our daughter another part of Massachusetts away from her college.
Top guest favorite
A view of a modern home surrounded by vibrant autumn foliage, seen from a tranquil pond. The lush greenery and colorful leaves frame the property, creating a serene outdoor setting with a small animal by the water's edge.
Home in Ashfield
4.95 out of 5 average rating, 67 reviews

True Shangri-la, Country Retreat

HillaryRating, 5 stars5 months ago
This home is in the midst of beautiful trees and well off the beaten path. My parents accompanied me to visit my daughter at Smith College, and they said they felt “at peace” in this place and would gladly stay there again. My father marveled at the heating/furnace system (he went down to see the huge pellet bag in the basement and wanted to talk with Mary about how it all worked), which is state-of-the-art and makes the large house a constant comfortable temperature. Mary was very responsive and kept us informed, and my parents visited with her when I was in Northampton for a morning. (My father said he could have talked to Mary all day.) For them, the staircase leading up to the bedroom was a bit challenging, and that would be the only downside to our stay. We had everything we needed, and our mantra whenever we were looking for something was “Mary probably thought of that.” Thank you for everything!
A two-story farmhouse, reflecting a rustic charm with weathered green siding and red-trimmed windows, is surrounded by lush foliage in vibrant autumn colors. A gravel path leads to a nearby barn, and a car is visible nearby, integrating the home into the tranquil rural environment.
Home in Leverett
5 out of 5 average rating, 5 reviews

Serene New England Farmstead Retreat

AndrewRating, 5 stars6 months ago
Adam was such a great host. He was extremely communicative and met us when we arrived to welcome my family to his property. The house is a beautiful farmhouse with so much land to walk. My dog loved being able to walk the property. The house was very comfortable, the beds stood out as being extremely comfortable. Overall, it was a great space for my family. I unfortunately had to cut my stay short due to something coming up back home, but the next time I go back to visit the Amherst area, this will be at the top of my list of places to stay.
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, 270 reviews

Light-filled Studio Apt. Near Smith

IsaiahRating, 5 stars3 months ago
Anna, bubba (the cat), and I visited the crows nest for the second time (and my third). It was wonderful, we love staying at the crows nest! It feels like we’re right at home and our cat loves running up and down the stairs. Theres plenty of hiking to do around, which was super fun to do in the snow. Carol and Robin let us know about a possible parking ban and where to park if that occurred (in their driveway), which we really appreciated!
Guest favorite
A cozy house, nestled among trees, is presented with a grassy front yard. An American flag hangs from the side of the building. A stone border outlines the driveway, which leads to a gravel path lined with greenery, enhancing the home's natural setting.
Cabin in Becket
4.86 out of 5 average rating, 37 reviews

Peace on the lake

CalvinRating, 5 stars7 months ago
We had a blast staying here! It’s right on the lake, which made for great memories kayaking and watching the sun set. The kitchen was well-equipped and the screened-in back porch was a great spot to eat dinner.
Guest favorite
A charming antique house is framed by a vibrant maple tree displaying brilliant orange and red foliage. Fallen leaves blanket the ground, while the warm hues of the house complement the colorful autumn landscape.
Apartment in Ashfield
4.87 out of 5 average rating, 247 reviews

Zachariah House Main St. Ashfield

MeadRating, 5 stars2 months ago
This was our second stay at Laura’s place in Ashfield. Great communication from the host who went above and beyond to make us feel welcome. We love everything about this cozy, historic home and would recommend for a relaxing stay in the Berkshires.
A spacious living area is captured, featuring a comfortable gray sectional couch facing a vintage wooden harpsichord. Natural light floods through multiple windows, enhancing the light-colored walls adorned with framed artwork. A vase of flowers adds a touch of color to the scene.
Home in Plainfield
4.73 out of 5 average rating, 156 reviews

Spring spectacular w fireplace, WiFi, BBQ & forest

MariosRating, 5 stars2 months ago
We had a fantastic stay at this Airbnb! The place was cozy, well-equipped, and perfect for our group. The kids loved the games and toys, and the fireplace made for a great place to relax after skiing. The location, just 15 minutes from Berkshire East, was ideal. That said, winter travelers should be prepared for challenging road conditions. It snowed heavily during our stay, and while private plowing services arrived, it was usually around 11 a.m. If it snows overnight, expect to shovel the large driveway to get the cars out early in the morning. The roads are steep and not always well-plowed, so a four-wheel-drive vehicle, winter tires, or chains are highly recommended. On our last morning, a tree fell out front, blocking the road and knocking out power. These things happen, and it wasn’t the host’s fault, but the remote location means services may be limited. Despite that, we had a wonderful time!

Family-friendly home rentals with a pool

Guest favorite
A wooden play structure occupies the backyard, featuring a slide, swings, and a small climbing area. Surrounding the playset, a grassy area is scattered with fallen leaves, and wooden fencing provides privacy. A couple of outdoor chairs are positioned nearby, adding to the inviting space.
Apartment in Northampton
4.93 out of 5 average rating, 215 reviews

Light-bathed 3br w porch in best downtown location

AllisonRating, 5 stars1 month ago
Perfect location for walking downtown and exploring the surrounding areas. The home is inviting, and the couch and beds are very comfortable. Instructions are clear and easy, and Sue has a notebook full of wonderful local recommendations. Our family of four felt very much at home and would definitely return.
Top guest favorite
A child relaxes on a clear inflatable float in a sparkling swimming pool. Colorful bubbles and additional floats drift nearby, while sunlight reflects brightly on the water's surface. The pool's uniform depth is visible along the sides.
Apartment in Northampton
4.98 out of 5 average rating, 305 reviews

Sunny Inspirit Apartment in best downtown location

EmilyRating, 5 stars1 month ago
Super comfortable apartment with thoughtful details left by host and great location - a perfect stay!
Guest favorite
A wooden children’s play structure is featured in a yard setting, accompanied by swings and a slide. Surrounding grass is mixed with fallen leaves, and a fenced area creates a sense of privacy. Bright sunlight enhances the cheerful atmosphere of the play area.
Home in Northampton
5 out of 5 average rating, 12 reviews

Sun-drenched 6BR Victorian steps from downtown

HerveRating, 5 stars3 weeks ago
Just What We Needed We had a marvelous trip to Northampton MA and Sue's large Victorian house was perfect for our group's stay. Of course it was clean and comfortable, but in many ways it had more than what we needed, from parking to rooms and other amenities, I was especially pleased to find convenient outlets and USB ports, even by the bed (which is better than some hotels I've stayed at). Sue had a welcoming gift in the kitchen, communicated responsively and helpful with ideas about the area, as our 'home' was truly conveniently located just blocks from the trendy downtown area. An enjoyable stay in a charming city.
Guest favorite
A round wooden dining table is surrounded by four elegant chairs. Light filters through the sheer curtains, illuminating the space. On the table, a bowl of fruit and placemats are visible. Colorful bird-themed artwork decorates the walls, complementing a vintage wooden side table.
Apartment in Deerfield
4.93 out of 5 average rating, 59 reviews

Nestled Inn

LorraineRating, 5 stars8 months ago
Enjoyed our stay. Frank and Manon greeted us and were very friendly. The place was clean, quiet and very comfortable. The refrigerator was very well stocked!! Highly recommend!!
Guest favorite
A children's play area features a wooden play structure with a slide and swings, surrounded by colorful autumn trees. The ground is covered with leaves, and the space is bordered by a wooden fence, creating a safe and inviting environment for outdoor play.
Apartment in Northampton
4.93 out of 5 average rating, 235 reviews

Wood, sunshine & movies in best downtown location

BrittanyRating, 5 stars1 month ago
This is our third time staying in one of Sue's Northampton properties (a different place each time) and, as always, the apartment was great. It's spacious, comfortable, and thoughtfully appointed. The location is wonderful, with easy walking to everything, and Sue is an excellent host. Highly recommended!

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