Pet-friendly vacation rentals in Berkshire County

This was a beautiful and well kept home and was a delight to stay in. Natalia was also a lovely and communicative host. We had no issues and would happily stay there again.

Paul was very responsive, kind, and hospitable! Really lovely home and land. Very peaceful setting. Would definitely recommend!

Shiyrah is a fabulous host. She is extremely responsive. Her house is lovely, well situated, very clean, and spacious. This is an excellent home, nestled amongst trees and green space, if you are visiting the Berkshires. 2 thumbs up!

My friend and I spent 3 nights at Chamio's home while we were at a clinic with our horses at a nearby farm. It met all our expectations and would definitely recommend.

Had a lovely holiday week in Nancy’s home! We felt right at home. The home was cozy and beautifully sun lit in the mornings ! Nancy had decorated before leaving and it was adorable and sweet. The yard was amazing for my 2 large dogs - they ran around and found toys to play with. The area was walkable with sidewalks that were mostly cleared after the snow. Hilly for sure ! Good workout hehe Super close to MassMoCA and the center of North Adams. Walked a few times with the dogs. There’s a dog run near by as well. A short drive from Bennington, Pittsfield and a handful of ski resorts. We had a great stay. Friendly neighbors, communicative host and lovely surroundings :) would love to be back!

Niki and Adam’s place was wonderful! Space for everyone, well equipped, comfortable and clean. Communication responses were quick and clear. All 3 generations of my family thoroughly enjoyed their home and its surroundings. Highly recommend!

Our stay at Mian and Anthony ’s place was fantastic! The house was impeccably clean and well-stocked with everything we needed. Mian and Anthony were very accommodating and provided great local tips. If we ever find ourselves back in the area we will definitely stay here again.

Absolutely fantastic stay! (this is our third time staying here) Rob and Julia are excellent hosts—welcoming, responsive, and incredibly flexible. The house is impeccably maintained, clean, and looks great. We loved our walks and runs around Sherwood Forest and swimming in the lake. This is our third time staying here, and we can’t wait to return!

Our group of 6 couples had a very nice weekend at Evan’s place. Very spacious which made our stay so comfortable. 5.5 bathrooms is a great amenity. The house is very well stocked with the basic necessities needed just like our own home. We enjoyed our stayed very much!

Had a great stay at Anna’s place! The kitchen and living space was amazing, kitchen was spotless and well organized, rooms were tidy and beds were comfortable. Everyone in the group wanted to save this place to return again once the pool opened up. The library and choice of books were excellent - I’m not much of a reader but even I couldn’t resist skimming some of the amazing cookbooks on the shelves. Thanks for the pleasant stay!

We had a fantastic stay at this charming home over spring vacation! The house is spacious, with plenty of bedrooms and bathrooms to comfortably accommodate our group. The kitchen was well-equipped, making it easy to prepare meals, and we really enjoyed the game room and cozy TV room for relaxing together. Although the weather didn’t allow us to use the beautiful pool, the outdoor firepit was a great alternative—safe, easy to use, and stocked with plenty of firewood. The rural setting made for incredibly peaceful nights and stunning views of the night sky. The house itself has an old-style charm with a unique layout that added to the experience. The host was wonderful—very responsive and attentive, making sure we had everything we needed throughout our stay. Highly recommended for anyone looking for a relaxing getaway in a quiet, scenic location!

A group of nine old college friends met at this lovely location for a weekend reunion. The house is exactly how it is described and incredibly clean and charming. The hosts were very communicative and incredibly accommodating. The kitchen was well stocked and had everything we needed to cook and feel right at home. The dining room is a beautiful space to gather and the whole house is comfortable, clean and inviting. We love that everyone had their own room and the bathrooms were incredibly clean with lots of extra products on hand. The bedrooms were streamlined without a lot of clutter and very comfortable beds. Everyone in our group remarked that they had a great night sleep. The house has a very interesting history and although it is an older home the owners did a fabulous job with updates and still kept all the original charm and character. Although the weather didn't fully cooperate, we were able to take a beautiful hike close by. We hope to get the chance to stay again next year

A truly amazing experience. I wholeheartedly recommend staying at Amanda & John’s home. You won’t find a better, more cared for, more beautifully appointed home. Everything you could ask for and more. Super kind, responsive hosts and every detail is considered. Great WiFi, too. If you’re looking for an experience in a spacious landscape, in quietude, with stars up above, this is the place.

Had a great time at Kelsey’s place. Everything as shown in listing and very well stocked with towels, linens, dishes, etc. Even though it was 53 degrees the kids still jumped in the pool! Would stay here again.

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.

I have nothing but wonderful things to say about Teva and his lovely home. The house is spacious, tidy, comfortable, and the surroundings are beautiful and peaceful. The beds were comfortable and everything you would need is there. We skied at Catamount which was ~20 minutes away - super convenient. Finally, and most notable, the overall experience and Teva’s attention to his guests’ experience was outstanding. He promptly and proactively reached out with local recommendations, was accessible during our stay for any questions, and made us feel right at home. We hope to come back over the summer for a little getaway.

Very hospitable!

Easy check in and very peaceful. Road noise minimal and lots of fans to keep the air moving. Lots of parking.

amazing! both the host and the house. secluded feeling. magical!

This was my second time staying at Maureen’s beautiful lakeside home and it surely won’t be my last. It’s the coziest, peaceful and inspiring place. Looking forward to future visits!

What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

We had a brief but lovely stay! The house is centrally located on a quiet street near downtown North Adams. Jennifer's directions to the house were very clear, and everything exactly as described. Would happily stay again.

Cute little spot in Adams. Right next to the small downtown strip of a couple of a shops and close to hiking at Mt. Greylock. Paula was very sweet and the home is cozy.

This is a great stay! Peaceful and you feel as if You are one with nature. Very clean. Arthur and Julie are quick to respond. Kitchen and bath have everything you need, including starter and wood for the wood stove. Cozy place right on the river where you can listen to the rolling sound of the river. Close to CT where we had a nice dinner at an old Inn with delicious blueberry cobbler. Beautiful Drive to norman rockwell museum, great Barrington and other Berkshire towns. We would most definitely stay at this home again.