
Family-friendly vacation rentals in Hampshire County
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Top-rated family-friendly rentals in Hampshire County
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Popular amenities for Hampshire County family-friendly rentals
Family-friendly home rentals with a hot tub

Riverfront Getaway
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!

Large Family Home Near Five Colleges
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!

The Farmhouse - Hot tub eclectic farmhouse 3 br
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.

The Creation Station
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

Escape To The Berkshires!
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.

Tranquil Lake Cottage on 3 Acres with Large Deck
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.

True Shangri-la, Country Retreat
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!

Serene New England Farmstead Retreat
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.

Light-filled Studio Apt. Near Smith
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!

Peace on the lake
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.

Zachariah House Main St. Ashfield
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.

Spring spectacular w fireplace, WiFi, BBQ & forest
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

Light-bathed 3br w porch in best downtown location
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.

Sunny Inspirit Apartment in best downtown location
Super comfortable apartment with thoughtful details left by host and great location - a perfect stay!

Sun-drenched 6BR Victorian steps from downtown
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.

Nestled Inn
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!!

Wood, sunshine & movies in best downtown location
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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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Six Flags New England
- TPC River Highlands
- Taconic State Park
- Mohawk Mountain Ski Area
- Bushnell Park
- Mount Sugarloaf State Reservation
- Mount Greylock Ski Club
- Hartford Golf Club
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Brimfield State Forest
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Rockledge Golf Club
- WIckham Park
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