Kid-friendly vacation rentals in Berkshire County

This lovely home is in the heart of Lenox. In warmer weather, it is walkable to the shops and restaurants of Lenox, or is a two minute drive. It's well located to discover the best of the Berkshires. The bedrooms were spacious and the family space was cozy, including a large couch for lounging and a lovely eat-in kitchen for meals. Great set up for a family. We loved our stay and are already planning for more visits for summer hiking and more local mountain skiing next winter.

We were thrilled with our stay in this Lennox home. It was right in town close to the local restaurants and a 5 min drive to Canyon Ranch for our spa day passes. The home is ample with 5 bedrooms yet feels cozy. Kendra was a great host, proactively checking in on us, giving clear communication and quickly helping us extend our stay by a day when travel plans changed due to weather. Just perfect for our long weekend getaway!

Michelle was incredibly gracious and responsive when we called late after our check in with a question about the heater. The place is gorgeous and you can tell that she pays attention to every detail and is doing all she can to make it a pleasant stay. The decor is perfect, the amenities are perfect. We had plenty of room to cook and host a dinner with four adults and two kids. We lit a fire, played games and relaxed. The bedding is so comfortable and we all slept so well.

fantastic and cozy, nice backyard, well equipped with amenities as well

Great stay at Mian and Anthony's place. Kitchen was well stocked with everything we needed, there was tons of space, and comfy beds. We are grateful that they allowed us an early check in too. Would stay with them again gladly!

The place was incredibly beautiful. The photos did not do it justice. It is in the middle of nowhere. Tina was very detailed in her instruction and one of them was that you must bring groceries because the closest grocery store is 30 minutes away. If you decide to book this place, read her detailed instructions. They are very helpful. The home offered a full kitchen which made it so easy for us to prepared our family's meals without struggling. The hot tub was such a treat. The basement had lots of games, a couch to launch and another TV. Perfect if you come with children. We were seven adults and we did not feel that we where on top of each other. The high ceiling truly made one of our boys (the giant) feel at home. Even the basement had a high ceiling. Pretty cool. Tina was incredibly nice and flexible. Check in is at 4 pm and we arrived earlier. We decided to contact her to see if it would be okay to check in earlier and she accommodated us. Thank you soooo much.

We stayed for a few days and the place worked out great! The kitchen is stocked with everything you’d need to include various paper products. Plenty of towels and linens for our family of 6. The entire home was very clean and well maintained. Great communication with Mike, and he even checked in on us to make sure we got settled without issue. We will definitely be staying here again when we travel back to North Adams!

had a great family get together with our kids and grandkids! The space was perfect for all of us and a great location for skiing at both Bousquet and Butternut! Many restaurants in the area and kitchen well stocked for making family dinners. - easy access to everything - Thank you Jon for the use of your house - made our weekend great!

Excellent location and decor, responsive host, off street parking, beautiful beds. Lots of art, all genres and media, an eclectic style with loads of personality. Our second time staying and we will be back again.

Mike and Wendy's space was exactly what we were looking for. it was comfortable with all the amenities of a personal home, it was very clean and welcoming. The fridge was stocked with drinks and condiments and the bathroom had extra toiletries! Great restaurants close by.

Beautiful, clean home just a few minutes away from the centers of Lenox or Lee in either direction! We had a great time relaxing and enjoying the food nearby :)

Everything you want in an Air-B-B . Clean and charming , right in downtown . We walked to restaurants every night. Lots of thoughtful snacks. Fresh Pint of whole milk and stick of butter in fridge. Host lived on site and was there to help with any situation. Great bedding and water pressure too.

Wonderful, conscientious hosts, great space - very comfortable, well furnished and fun, and great location to downtown.

The stay itself was wonderful! As advertised, it was well within walking distance from the downtown area, was cozy, and looked exactly like the pictures showed. 5/5 stars What pushed it over the edge from a good Airbnb to GREAT, was the attention Jennifer paid to small additional details - little chocolates to welcome us, snacks intentionally set out for us, water bottles, and a few other things speak to how good of a host she is. 6/5 stars 5/5 stars for Jennifer and her lovely apartment, 3/5 stars for Airbnb: we didn't get a message from Airbnb until we were checking out that her messaging wasn't working, so a couple messages went unanswered. Jennifer had put her number in 3 different locations explaining this, so she was super proactive, we were just a little unobservant in seeing that.

Very happy with our stay at Frank’s in North Adams. Super friendly host and perfect place to enjoy a mixed bag of weather, mostly decent for early April, easy and content to both go out to see the city and just stay in to hang out in the three season porch or watch a movie. Great recommendations from our host for outdoor places to check out. Walkable. Peaceful. Would hope to stay here again

The apartment was a clean and cozy space near Williamstown and exactly as described. We appreciated the flexibility with check out.

We had a wonderful stay at the condo - ideally located, spacious and comfortable and had everything we needed ! Definitely will be back! Elisabeth was generous, responsive and super friendly and excited for us for our trip!

Beautiful apartment with lots of rooms-comfy sitting areas and lots of light. It was very nicely appointed and the checkin was simple. We will definitely be back as the location is ideal.

We had a wonderful stay at Jiminy Peak.. hosts were super quick to respond with any questions. Very easy check in and check out. Will definitely be staying again in the future!

This is our second time staying and we loved it even more the second time. Christina was lovely to book with and the unit we were put in had recently been renovated so it was in great shape. You really can't beat this place for a winter family vacation. The space was clean and well appointed. I'm very finicky when it comes to hotel cleanliness, there were a few notes I'd give on the space but overall I was very happy with the space and our overall stay. The staff at Wyndham were very helpful and friendly. We will definitely return again!

As described and walkable to local coffee houses and rail trail with Mass Moca a 10 minute drive away. The host was very communicative and helpful with clear directions inside the unit.

Our second year staying here and making wonderful family memories. The condo was clean and cozy. Gorgeous view of the mountain and easy ski in/ski out. Everything you need is stocked and ready. We look forward to rebooking for next year.

We loved staying for the weekend at Katie’s place. We walked to great restaurants and Mass MOCA museum. So cozy and relaxing all around!

Had a great stay at Jo-Anne’s for a wedding as MASS MoCA. Space was clean and cozy. Bed and pillows were comfy. Very walkable to places around town. The cars driving by were a little loud for a light sleeper, but with some earplugs it was fine. Jo-Anne was very helpful and responsive.