Family-friendly holiday rentals in Berkshire County

Beautiful location. Perfect yard to sunbathe and enjoy the scenery in the mornings and evenings. Enjoyed all the amenities such as the hot tub and pool table with my group. The house was a perfect fit for my group of 7 + a dalmatian, there would have been room for 1-2 more people before it felt too tight. Didn’t have any trouble with cooking a steak and veggie dinner at this location, there were enough tools for us. Would recommend bringing your own spices and seasonings though as the spice cabinet was only stocked with salt, pepper, and a couple sprinklings of other basic things. The instructions to get to the house were a bit unclear and hard to follow after a long road trip up. Eventually found the house and was pleasantly surprised. The photos don’t do it justice! Definitely a hidden gem and would go back again!

This was our 2nd stay at this property. If you love the Berkshires and all the activities available, this house and property are perfect. It is very well maintained and the great room is perfect for our large family. Nothing like the hot tub and sitting around a fire after a busy day of hiking and Tanglewood. Wendy is an excellent host, never a problem.

Our stay was excellent. House was exactly as advertised and fit our needs perfectly. We were a large group including young children and everyone had plenty of space both for sleeping and recreation. Kitchen was well stocked with anything you needed to cook your meals. Host was responsive and very clear with instructions and answering questions. 5/5 stars. Would highly recommend. A quick note for future guests. If the weather is cold the kitchen floor gets cold. Would recommend packing slippers.

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!

Great resort. Very nice pools (indoor and outdoor). Nice quiet setting very relaxing

The place is spacious and clean. Small issues were fixed quickly. I recommend connecting to the host via text message, rather than the Airbnb app, because some Airbnb messages were not received. The house is located close to Jiminy Peak and sits on a secluded lot, quite a distance from the road, so you don't hear passing cars. I highly recommend using a car capable of 4-wheel drive if you arrive in the winter. Even after the host had the driveway plowed, it tends to be icy and very slippery in the winter, as it is very long and steep. The beds and living room were very comfortable. The wood fire stove is in the vestibule, when you take off your shoes. It is not like a fire place in the living room. We have a nice stay.

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!

We had such a great time at Rob&Julia's place. Very good communication, great location, the place was sparkling clean! I will definitely come back again with my family! One of my best experiences

Another perfect stay at Laurie's. This is our third stay over Thanksgiving week and we always are sad to leave. My family absolutely loves staying here. There is plenty of room to gather or to have some alone time. Beds are comfortable. Kitchen has everything you could need and is always pristine. Check in is stress free. Area is peaceful and serene. Lee is a lovely New England town. Downtown is less than a 5 minute ride. Many restaurants within a 5-20 minute ride. Outlets are 10 minutes away. Looking forward to our stay next year.

We had a great stay at Shiyrah’s home! We were a group of 2 families with three little ones with us. The house was perfect for us. Shiyrah was so accommodating, allowing us to check in early with all the kids, as we were arriving for a wedding weekend event a bit before the typical check-in time. She even messaged me the morning of our check-out saying to take our time and not to rush. She is a wonderful and thoughtful host, and her house is a beautiful place to stay. Thank you so much, Shiyrah!

Our friend group really enjoyed staying here on a rainy weekend in May. Hanging out by the wood burning stove and doing puzzles at the table was a highlight, and our dog loved being able to be outside on the dog run. The location was fantastic - right in between Lenox and North Adams - so we were able to access museums and hikes easily. Would highly recommend!

Highly recommend this lovely home. Beautiful and peaceful surroundings. It was so peaceful and relaxing. You shouldn’t miss out on a Great and Beautiful Place like this. Plus you’ll get to see Beautiful wildlife walking and running around.

This was our 2nd weeklong stay. The space is clean and bright. Heating details were clearly explained. It was quiet and peaceful but only a 7 minute drive for milk I forgot to bring for coffee. We saw a small bobcat in the front yard on our last morning. Beds were very comfortable. Hosts were friendly and responsive. I’d recommend this place to friends/family and hope to stay again.

Our family loved our stay at this house. It is a peaceful and serene setting in a beautiful wooded area. The host was very accommodating on short notice. The house has a very nice and inviting interior, it feels very homey and comfortable. There are many nice places for a hike and the view at the top of the hill on the property is quite scenic, we could see the Catskills to the south. There are all the modern amenities, and the (decorative) antique wood burning stove in the kitchen was a neat touch. I would definitely recommend this place!

Spacious and comfortable one bedroom + studio, lots of natural light, serene atmosphere, we had a great stay and would be love to visit again

The airbnb was close to town. The house was very clean and comfortable.

We had a great stay at Michelle’s place. It was very conveniently located to the base of Jiminy Peak, which made getting to and from the mountain very easy. The house was very well appointed and had everything we needed. We used the fireplace twice and it was super easy. Having access to the facilities at The Country Inn at Jiminy Peak was great as I am injured and can’t ski currently, so instead I went to the gym each day. My family didn’t want to leave and my kids are asking when we can go back!

Our group of 10 family members and close friends had a wonderful time at this lovely house. It's large, clean, comfortable, and well equipped for cooking and relaxing together. The instructions were clear and comprehensive. Jay is friendly, knowledgeable, and responsive - in short, an excellent host. Our whole experience gets a big thumbs up!

We had an amazing stay with our toddler. Dorothy’s place was large, clean and d peaceful. The pictures don’t do it justice. The outside space is fantastic. The kitchen was stocked with everything we needed and we really felt at home there. The location was close to shops and restaurants. Thank you for the fantastic week!

This was our second stay at the Queechy Lake house and it did not disappoint! The home is wonderfully maintained, fully equipped and cozy - we appreciated the new additions of the pool and backyard activities. It rained most of the weekend but we utilized Meredith and Jason’s local recommendations and had a blast.

This was a great place to stay as a family for a ski trip! Easy ski on/ski off access to the mountain with ski lockers was a huge plus. Easy enough to walk to a few restaurants. The kids love the movie theater, pool and game room. Very clean and friendly/helpful staff at front desk.

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.

Great stay. Bathrooms r small and outdated but the fireplace and hot tub and property outweigh the cons.

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.