Family-friendly vacation rentals in Pioneer Valley

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!

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.

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!

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.

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.

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.

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.

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.

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

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!

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!!

A lovely place to stay. Beautiful view of the animals and mountains. Host was nice and accommodating.

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.

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.

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.

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.

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.

Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.

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!

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.

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.

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.

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!

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!