Family-friendly vacation rentals in Williamstown

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!

Place rules, hot tub is nice. Water pressure in shower could be a bit better but overall a great stay

Fantastic space for a large group. We had 10 people for a New Year’s Eve ski weekend, and this was the ideal spot for it. Hot tub was a great treat. Be warned - the floors are squeaky, so if you’re a light sleeper in a large group bring ear plugs.

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!

Beautiful farm stay. We loved watching the sheep and the local birds. A great dirt road to go for a walk on. Gorgeous views and a lovely property. The house is beautiful and the hot tub was great!

Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.

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.

This was my 2nd time staying here and yet again exceeded expectations! Absolutely love this place. It's comfy and cozy. Miriam is always quick to respond when needing anything. Place is very clean, beds are super comfy. The jacuzzi bath tub is amazing and so relaxing. Would Absolutely stay here a 3rd time!

Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!

Our stay at Maple Hill Farm was so peaceful and exactly what we wanted. We loved being amongst the animals and nature and it was such an incredible hidden gem that we will think about for a long time after our trip has finished. Philip was an incredible host and we loved meeting his sweet pups too. Can’t wait to come back again!

We loved our stay at this beautiful house! It felt like home when we arrived and we appreciated the opportunity to check in early. There are multiple sitting areas both inside and out. Three bedrooms and two full baths are upstairs with two separate stairways and provided privacy for our group. The kitchen had everything we needed and it was nice to have spices available for our use. We enjoyed the long trail just across the street, and easy access to local markets and restaurants. We'd love to return!

Nice stay in a comfortable apartment. Friendly hosts in a quiet neighborhood. Close to town and local attractions.

The place is ideal, even if the weather isn't great the house is really spacious and cozy. Laurence and Ilze were communicative and very sweet, would love to come back!

Mariann has a great space in a great location. Very accommodating and friendly, made you feel very welcome . Very responsive. Really nice area. Would highly recommend.

We had a great experience with Erin and our stay! Erin was incredibly friendly and welcoming. She made sure to respond promptly to all our questions and requests, which really made us feel at home. Erin went above and beyond to accommodate our needs, ensuring we had everything we required for a comfortable stay. Her genuine care made our experience truly special. If you're looking for a wonderful host and a cozy place to stay, I highly recommend booking with Erin.

Donna's place was a wonderful weekend stay! Beautiful property and guest house. Well appointed and care for. Just a few improvements that would have made our stay even better--a small microwave for quick reheating of coffee/leftovers, a luggage rack and place to store/hang clothes, and ensuring the driveway and a walking path are cleared of snow even when out of town (with thawing and refreezing, we had to navigate two inches of solid ice, which was terrifying both on foot and in the car).

Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!

Large house in a very remote area. Approximately 70 acres. It was very relaxing and was nice to enjoy the pool which was professionally cleaned before arrival. The master bath has an incredible view of the mountains and an enormous shower. Pool table was fun and well taken care of. We stayed on probably one of the hotter weekends and the house cooled down at night pretty well just by opening the windows. Most rooms had ceiling fans if no other fans were provided. I can imagine this house would be amazing in the winter or fall too. With the screened in fireplace room and additional fire place inside the main house. You’re also close to 2 ski mountains each about 18 miles away. I could see myself renting again in the future. Thanks again

We absolutely loved staying here- beautiful and laid out perfectly for 2 families, each with 2 little kids. Super convenient location to Mt. Snow. We look forward to staying here again!

there was lots to do inside the house as well as outside. everything was amazing

Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!

We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.

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.

Nice, private, large room. We loved the real flame of the franklin stove. Little mini-kitchen. Nice duvet on good queen-size bed. Very private, separate building. There is a swimming pool, but that's summer-months only. We liked that it was just a 5 minute drive to Williamstown and the Clark. Not really enough hot water for two showers in a row, but other than that, great. Well appointed, with shampoo, Q-Tips, salt, sugar, etc.