Pet-friendly holiday rentals in Bennington

The host was extremely responsive and kind. The Airbnb its self was beautiful and private. It was peaceful and spacious. Everything in the description and pictures were accurate. I recommended this place to family who always come to visit the area. So happy we found this place and plan to rebook again in the future.

We loved our stay here!! It was the perfect getaway for a long weekend. The property is beautiful and private but close to anything that you might need. The kitchen was super well stocked, beds were comfy, and we really appreciated the firewood supply. Nikki & Topher were great hosts - extremely responsive to all questions we had and proactive about check in/check out instructions. Would definitely come back!

This home is certainly one that feels like home when you walk in the door! The warmth of the wood and decor, and little touches throughout, let us know how loved this home is. We had everything we needed for our 2-plus week stay, and our hosts were incredibly responsive and kind. It was lovely to hear the owls and running water at night, and I can imagine how lovely the fireplace would be to use during the colder months! Thank you for a lovely stay!!!

Fantastic property and great host. We loved our stay at this property, especially the view from the hot tub on the deck!

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.

Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.

Loved our stay ... We had a nice family dinner , could sit out on deck and enjoy the gorgeous view and our meal and then were able to take a short hike up the back trails and enjoy the gardens and store .... Hannah was awesome and very responsive and checking in to make sure that we were all set .. Thank you so much for allowing us to stay and enjoy our stay. We had a perfect weekend. Thank you, Garry and Family

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.

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!

We had a great stay. The apartment is peaceful and clean. I particularly loved the soaking tub! Jared was very responsive to all my questions and provided great coffee for the morning.

clean bathroom, cool shower.. bed was clean..loved the all 4 wall windows, and door to upper deck small fireplace, and charcoal grill..about 4 min drive to the main boardwalk

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

Very clean. Well furnished kitchen. Spacious. Good value.

This was my third time staying on Rosalind's property, but my first time in the "retreat" unit. The space is better in person than in the photos! It's a spacious two level unit with a huge bedroom/loft type area, perfect for setting up your yoga mat! The high ceilings and large forest facing windows in the bedroom were a highlight for me. Rosalind has always been a very responsive, thoughtful, and flexible host. I can't wait to stay again!

Lenore's place was very cozy. We felt right at home. We added guests (including a dog) after initially making our reservation and it was no problem with the host. Just a note, it costs a fee to add more guests on Airbnb. Overall our stay was lovely and our hosts were very nice, responsive, and welcoming. 10/10, would recommend.

Peaceful, Serene location just 10 minutes from Stratton. We enjoyed the use of the new hot tub, and roomy kitchen. This space is surrounded by nature with plenty of space for you and your group. Would definitely stay here again!

Very nice stay- Beverly was really friendly and helpful. The river nearby is lovely and the place has every amenity you could need. I wish I was a bit more prepared - I have Verizon and didn’t get service at the place or in the small town. I had to drive 10-15 mins towards Manchester. She communicated that there is WiFi at the library and a store which are super close but I didn’t try to access. It made directions or looking up restaurants a bit tricky

Chris's place is a beautiful cabin nestled in the woods, with birds singing, beautiful airy feel to the cabin, roomy, lovely second floor, most comfy bed I've ever slept in. Loved the colors - wood, tall glass windows and skylights, dark green comforters and pillow covers. It's up a dirt road, neighbors are far away, so if you don't like remote, this isn't your place. But if you do, it's perfect!

We had a wonderful visit with our family. The home is just as pictured on the website. We had everything we needed to cook good meals and relax together. The setting is beautiful. We enjoyed the views driving around the area. We were too early in the summer to do any water activities safely. We had some great walks in Molly Stark State Park and on the Valley Trail recommended by Danielle and Ben. Note there is little to no cell service at the site of the home. WiFi access was very stable. Cell service improves in town.

We LOVED our stay at Rebekah and Erik’s house in Bennington! It was the perfect location for walking into the town. The amenities were outstanding and the decor was beautiful! We highly recommend this home! Thank you for a wonderful stay!

I had a blast in the beautiful Chalet. Everything was what I was expecting and more. The review matched the property and vibes. From the beautiful views outside to the cozy vibes in the loft upstairs, it was amazing. I had a couple of questions for Jason and he answered insanely quick and was very helpful with his information. The Pac-Man was a great addition too. P.S 24,910 is my high score!! I totally recommend and might even come back some time in the future. The host, cabin, property, and area was delightful, nothing but love for this stay!!

A wonderfully quaint cabin that is a perfect landing spot for a weekend getaway with all modern amenities. Will definitely stay again when in the area.

Great place! We came for a wedding in Saratoga and it was conveniently located for us and there was a lot of places around even though the place was on a very secluded country road. It was clean and the bed was super comfortable and the kitchen was nice too. Thank you !!

It was a wonderful stay. Whether you’re just looking to relax or for a little adventure this stay offers it all. Even though it was a rainy stay they offer plenty of movies, books and games.