Family-friendly vacation rentals in Bennington County

Wonderful stay. The location was private and relaxing. The home was well stocked with all the amenities. Having the lake and kayaks available was perfect. Summer evenings under the stars and fireflies. Host was responsive and friendly. Look forward to staying again!

I have to say this is THE BEST Airbnb in the area if you’re skiing Stratton. The house itself was everything you need, spacious, clean, well stocked., designed and decorated with a beautiful taste. The beds were large and comfy, shower pressure perfectly strong, heater fast and functional. The location was convenient too, with easy access to the shops and restaurants in Manchester. Paul was a wonderful host and very helpful. We definitely would love to come back in the near future.

Our GPS took us to the other side of town first, but it only caused a few minutes delay and allowed us to drive through the beautiful Main Street in the evening and gave us a sneak peak. The airbnb is a cozy, private finished space above their 2 car garage. The view off the balcony was incredible in early October. Our hosts were very friendly and allowed us our space and respected our privacy. The queen bed was cozy, and the shower was clean. The mini fridge was stocked with some beverages, coffee and cream. It was a great space for a weekend getaway especially because of the hot tub.

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.

Great location. Beautiful views. Host was extremely responsive. Great fire place and living room.

Great space! Lots of space to entertain for our group of 10. We also had my four year-old niece with us, which worked out because is also a very family friendly house with games to play and things to entertain kids as well. The kitchen was a great size. Plenty of space from multiple people to be in doing their thing. The hot tub is also amazing, very spacious with the perfect depth and a variety heights for the seating inside the tub, the tub sits about 10 steps from the back floating door off of the living room/den area and has breathtaking mountain views! If you’re heading to this area of Vermont and to have a larger group with you this place is perfect for your trip!

Stayed with my family of four for Christmas week. Close to Shaw’s grocery and several restaurants. We went skiing at Mt. Snow and Okemo. The club house had a pool/jacuzzi, ping pong, pool table etc. and friendly staff. The house was very cozy and comfortable. Micheal responded quickly to any questions and was easy to communicate with. Would stay again if we return to the area.

I enjoyed staying there. It was extremely comfortable. Mostly quiet, though if someone was renting the upstairs (a little less than half of the time I was there it was occupied, I would say) the floors transmitted the noise a lot, being the nature of old buildings. Neighbors were very nice though and tried to be quiet. Overall it met and exceeded my expectations.

Daniel's cabin in the woods was comfortable and cozy, and only a 5 minute drive from the Sunbowl lot at Stratton Mountain. It was perfect for me and my kids for a weekend ski vacation, and the icing on the cake was the the sauna which was so relaxing each afternoon after skiing.

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.

Amazing views. Amazing privacy. A beautiful couples retreat! Fireflies at night and rainbows in the backyard made this stay very special.

Very responsive host who went above and beyond to display hospitality. Clear instructions and let us enjoy the place in peace. Space itself was warm and inviting and perfect for a couple's weekend away.

This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.

We had a lovely time at Maura’s house! Maura was friendly and responsive and clearly loves to share this beautiful area with guests. The house was spacious and well kept. (I would note for those who might mind that there were some family photos, magnets, etc. up, but that didn’t bother us at all!) The house is about 10 minutes from Mass MOCA and less than 20 minutes to Williams College.

We had a wonderful cozy weekend with friends. Leopold’s place was private and tucked away with beautiful snowy Vermont scenery. We went skiing at Okemo (30 min drive) and then relaxed in the cozy living room. The shower was great and the bed was super comfortable. Thank you Leopold!

Thank you Colleen for sharing your home! my sister and I truly enjoyed the peaceful location, and the sound of the bubbling stream right outside was super relaxing! You made it easy to use, and responded quickly when I messaged you. We didn't see any book to leave comments about our stay, but know that it was just what I needed to relax from my stressful job! THANK YOU!!!

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

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!

We were in town for a family wedding and this was the perfect place for 20 or so of us to spend the weekend. Everything was great. We were so comfortable and had so much fun! Thank you to Meiling, Martin, Mayra, and all the folks who assist them with housekeeping and logistics. Hope to find an excuse to return, as everyone was sorry when our stay came to an end. Highly recommend without hesitation.

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.

Husband and I had a great little ski getaway at Mt Snow. This cozy place was perfect for us! The view of the mountain is awesome. We did find the walk to the mountain (although short) with ski gear to be a bit much and highly recommend taking the Moover shuttle from the nearby parking lot.

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!

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.

Our stay at Carl’s listing was more than we could ask. The location is perfect to the mountain and the shops and restaurants in the village. Carl was very helpful for the check in process and was very responsive. The space was very large and clean. We had the best time and I would certainly stay here again in the future!! The amenities at the lodge were amazing and the lodge manager was so incredibly helpful and friendly as well. A happy and fun vacation!!