House vacation rentals in Bennington

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!

Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!

Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

Great stay and was exactly what we needed for our entire family for a weekend wedding!

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

My family had a fantastic stay! The place was exactly as described—clean, cozy, and well-equipped with everything we needed. The location was perfect. The host was incredibly responsive and made check-in a breeze. All the details and amenities was so thought out made our stay so easy and convenient . We felt right at home and will definitely stay here again. Highly recommend!

Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

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.

This place was exactly what we needed to escape and unwind. So relaxing, cozy and comfortable.

Daniel's place was the perfect home base for our Berkshires getaway. We visited Mass MoCA and loved coming back to this quiet, peaceful retreat. The backyard was especially serene, I enjoyed my morning coffee outside and relaxing by the fire at night. One of my favorite parts was cracking the window open and falling asleep to the soothing sound of the brook out back, pure magic. Daniel was a gracious host, friendly, responsive, and thoughtful. The local charm added so much to the experience, including camels and other farm animals across the street, Farmer Dave is a gem. We'd happily stay here again!

This was our 2nd time stay at Delia’s place. Everything was as described and clean. Great spot and will stay again.

We were very grateful to find such a welcoming place that would accommodate our two (well-behaved) dogs. The place was lovely and we were happily surprised to find that the sofa bed was in a room that could be closed off, so it really made it easy for us four adults (two couples) to have our own space. Listening to the river across the street was melodious and beautiful. Such a peaceful stay. Thank you!

Nick says: We had a wonderful time. The school house is a product of love and dedication. It feels modern and expansive and at the same time maintaining the historical details of a charming old school house. Connie was responsive and professional and provided everything we needed. The house is near a beautiful hiking trail and provided a very relaxing stay.

We can’t say enough about the comfort and beauty of this home. Maura communicated with us regularly and provided coffee, tasty treats for breakfast, and snacks! The kitchen is fully stocked and was very helpful for our family to make our own meals. Sleeping on the porch was a joy! . I’m glad we got to briefly meet Maura; if we ever come back to the area, we hope to stay here again!

Great little house close to trails. Was perfect for our visit to the Mt Prospect Nordic center. The house was very comfortable and we enjoyed the games and books in our downtime. Would recommend a stay here!

My husband and I spent a long last winter weekend here. The condo was perfect for ski on/off and we enjoyed a day on the mountain. Though the weather wasn’t great the whole time, Brittany & Jen were quick to send recommendations for things to do, trails to hike and their favorite restaurants. So close to lots of great spots in this little mountain town. We would absolutely stay here again

Our stay at the lake was truly amazing! The house was impeccably clean and well-maintained, and the location was perfect for enjoying the lake. Lisa was incredibly responsive and helpful throughout our stay. Highly recommended!

We had a wonderful stay! We were able to snowmobile right from the house and enjoy the scenic views of the lake.

Wow, what a perfect country getaway. Our nine guests in the house had a lovely time. There is an outdoor dining area under a charming old tin roof where we had several meals. The setting was amazing. Old front porch looked out on a country road with fruit trees. Lots of room for various gatherings. The photos don't do it justice. Would come there again!

Gene’s house is a place of peaceful quiet and beauty. It’s well appointed and comfortable, with wireless and all the various conveniences, but it’s far more than that. The separation between the interior and the beautiful meadow and forest outside dissolves through Gene’s use of windows and glass doors, and the calming sound of falling water can be heard in every room. His use of color and symmetry create an environment that allows you to decompress, and as a result, you can’t help but to connect with the beauty of the forest. The waterfalls are wonderful to sit by; it was too early in the season for a swim in a cold mountain stream, but that’s just me. The design and setting of the home is a reflection of Gene. If you visit, I recommend that you get to know him a bit. His kind attentiveness makes him a first-rate host, but it’s part and parcel of his uncommon connection to the world around him. Gene was more than a host to us- he became a true friend. We will be back.

Andrew’s place is great, right on the river, lots of light and plenty of room to spread out. Hope to come back soon.

I really enjoyed my stay. The house was very peaceful with a great view out the front window. A very nice country home to stay at.

I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

This is a delightful place! It's very near town but off the road so it's quiet. The house is larger than I expected and extremely tranquil and restorative. The sound of the creek just outside the porch is incredible! And Marin was a lovely and responsive host. Highly recommend.