Family-friendly vacation rentals in Bennington

Nice place thanks Mike

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.

Had a great time at this beautiful home! Felt super peaceful and great for groups. Thanks so much!

Bob’s place is great for several families. Many bedrooms, multiple bathrooms, great amenities and close to skiing!

My friends and I had a great time at this place! The home was beautiful and very spacious - we were able to all hang out in the hot tub, kitchen, living room, and no place felt cramped.

Great house, location, and host! Eric was very helpful, communited timely, and is super organized. The house is in a great private location right near Okemo, plenty of restaurants, and a grocery store. The house felt bigger than the square footage states and was perfect for our two families (4 adults and 4 kids aged 9-12). We are usually disappointed in how clean rentals are upon our arrival, but this house was basically impeccable which especially isn't easy in the mountains! The upstairs is perfect for a kids room and the living space was nice and cozy, but didn't feel small. Plenty of room for everyone. I highly recommend this house, the hosts, and Okemo. It was our first time on this mountain and really enjoyed the family friendly atmosphere and terrain while also having plenty of advanced trails as well. Overall we had an A+ weekend.

This is a lovely home in a beautiful setting. It is quite close to Stratton and the hosts were all great communicators with a quick response time. I hope to stay there again sometime!

My family and I had a wonderful time! Larry is very sweet, gave us a tour, offered to help with docking our boat and even offered my husband the tools to fix the bunk on our trailer. The house is big and beautiful!! Very clean, the beds are comfortable, the kitchen has everything you need!! The hot tub is definitely a bonus as we used it everyday!! The dock was perfect, we had room for our pontoon boat and jet skis. All around the perfect place for some R&R!!! My family and I love Cossayuna Lake as we are semi local and it was our first experience with an Airbnb. Thank you Larry for sharing your home!! Highly recommend this for your next vacation!!

We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!

We were extremely pleased with our stay at Roberta’s place. This was our first visit to Saratoga Springs, and we wanted a quiet place that was convenient to downtown and that would allow us to fully experience the community. We felt at home from the moment we walked into the place. The neighborhood was quiet and peaceful, and the apartment was very comfortable. The unit was exactly as described and came with coffee for the coffee maker and even a package of scones for us to enjoy. It was a short walk to the restaurants and shops of downtown, and we felt safe walking at all times. Overall, we highly recommend Roberta’s place. We will definitely stay again the next time that our travels take us to Saratoga Springs.

Second time staying here to hike the area trails. The place was immaculate as was my first visit. The hosts are wonderful and helpful. They gave me check in flexibility that added a lot of time to my plans for the day that ended up being a big value. Highly recommend.

Nancy’s place was a great option for my stay in the area. The kitchen had everything I needed, and the couch was comfortable. As was the one bed I slept in. I was visiting for a work trip. Nancy was also incredibly responsive to any questions I had, and was offering suggestions for the area I found useful. I’m glad to have found this place. While on this trip, I did not bring my dogs, I will be sure to stay here on my next one to the area. I typically stay in hotels here, but I will do my best to stay at Nancy’s anytime visiting in the future.

We enjoyed our stay at Domenic with 2 kids on school break! The tiny house is just as described, colorful, well organized and very comfortable. We enjoyed making a fire outside on a beautiful spring evening and checking out the peacocks!

I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.

Dan’s place is wonderful for a quiet, romantic getaway. We loved the deck and the big green space to walk our dog. The apartment was spotless and smelled clean. Dan was very responsive and helpful. My wife and I are hoping to come back someday!

We really enjoyed our stay at this lovely house!! So many cozy nooks and Miles and Ruth were very responsive and helpful hosts! Would definitely stay again :)

A fun winter break/birthday getaway! Sarah’s house had plenty of bedrooms for all guests. The game room, pool table, and wood stove/fireplace were great to have on these cold February days. Everyone enjoyed the sunroom and large dining table. The hot tub and outdoor sleds were used as well. The history of the house and beautiful views from the property were an interest to all. I bet this house is a lovely spot in the summer as well!

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

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.

We had a lovely Labor Day weekend stay at Julie’s house. There was lots of space indoors and out. The hot tub, pool, fire pit, and grill were all put to good use and made our stay so homey and comfortable. The kitchen was well stocked with all the tools and appliances needed. The location is excellent with easy access to 87, SPAC, and the race track.

There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

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

Leo and Michelle were very responsive with any questions we had, and even reached out to offer us an early check in. The location was close enough to our places of interest, while still being slightly rural. The place looked just like the pictures and we felt right at home. We will stay there again when we return!

The house was beautiful and Rhonda was great, she was very responsive and helpful. We felt right at home and enjoyed the place more than Lake George :) , the hot tub and pool were great and i would recommend anyone coming to this area to definitely book the place if they get the chance.