Pet-friendly holiday rentals in Berkshire County

Our group of 5 were very happy with our stay in Lenox. Location was perfect in that it was close to everything we had planned in the area. Everything went very smoothly in booking the rental and all the communication involved. The place was very nice.

Home is very beautiful. Jim and Susan were very responsive when needed we felt right at home everything was right at our fingertips when needed. We came for a weekend girls getaway and this home helped us achieve that peace we needed. Very spacious we will be back again.

Our friend group really enjoyed staying here on a rainy weekend in May. Hanging out by the wood burning stove and doing puzzles at the table was a highlight, and our dog loved being able to be outside on the dog run. The location was fantastic - right in between Lenox and North Adams - so we were able to access museums and hikes easily. Would highly recommend!

Jaclyn’s home is the perfect place to get away and relax. Being on the water with a wood burning fire place was absolutely lovely. The home was clean, well organized, and Jaclyn was always responsive when we had a question. The home was an easy 20min drive to a lot of fun small towns. There was a little traffic noise when we were outside from the highway, but it was peaceful otherwise

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!

Great stay! This is our second time staying at Bradley’s place and it was exactly the same as last time, in a good way. Place was clean, great neighborhood, very quiet!

Thank you, Salome, for a wonderful stay. Our extended family felt very relaxed and comfortable in your lovely home. It was a rainy weekend, so it was especially nice that there was a pool table, a fuzeball table, and lots of places in the house to hang out together. The bedrooms and bathrooms were lovely and the shared space was large and inviting. We enjoyed making meals together in the open kitchen. And the neighbor was so picturesque! We loved staying next door to the horses and donkeys, and taking walks on your beautiful farm-filled road. Thanks so much for making our stay such a special weekend. We all hope to ba back again! Very best to you and yours, Joanna and family

We loved staying here at Matthew’s Barn House. The location is not only peaceful and private, but we were able to completely unplug from our busy lives and enjoy time with our family.

Beautiful, cozy accommodations. Comfy bed. Upscaled shower products. Wonderful towels. My husband said great coffee! The pool was inviting, but the weather was not cooperative while we were there. The actual space in the room is on the smaller side, but cozy enough for us two and our cockapoo. It was ultra convenient to our daughter’s house only 10 minutes away. We were there for family time but great recommendations for the area were given.

I think this is the most beautiful air BNB I've ever stayed at. The property is super big and perfect for families. There are a ton of bedrooms and bathrooms and the living area is so beautifully decorated. The kitchen was well stocked and really modern. There's tons of stuff to do right in the home so you don't have to venture away, but if you do you're very close to everything you'd need. The pool was pristine. There were gorgeous fire flies putting on a show for us every night. The view was incredible. We even saw a rainbow on our last day. It was peaceful and private. I highly recommend this place and the hosts. They were super responsive and went above and beyond to accommodate us when we were dealing with some car troubles. Thanks for the incredible stay!

Melissa and Geoff's place is in beautiful surroundings and well within a short drive to excellent restaurants, museums and outdoor activities. We were there during an especially rainy and cool period, but the apartment kept us toasty and warm after a day of dodging the raindrops. The king size bed was lovely and a white machine lulled us to sleep. The deck attached to the house was wonderful and when the weather looked as if the blue skies were here to stay, Melissa asked if we wanted dry cushions for the chairs- just a lovely thought. The gardens were just beginning to bloom and the property is spotless. We will definitely return to Sweet Dreams; the apartment was a pleasure to be in. Andrea and Ray

Stayed here with three others for work. The house was clean and well updated. We had no issues and will look to stay here again.

We selected this amazing property as the location for our mini-wedding and we could not have been happier. The house is brilliant in every way. The floor plan, the furnishings, the decor, and the grounds are all thoughtful and stunningly beautiful. The property manager was always responsive and kind. This is truly a top property and you will not be disappointed. We cannot wait to visit again.

We had a wonderful stay at this adorable home in the Berkshires! The house was very comfortable and cozy, and the backyard with the deck and pool provided a wonderful space to hang out day and night. The house was situated 20-30 minutes from so many places - downtown Lenox, Miraval Spa and Ballderdash Winery. We can’t wait to come back!!

We had a wonderful stay at this beautiful property! The location is close to plenty to do and great dining but also feels very private. The home is absolutely beautiful as pictured. The pool was a real treat to have and half of the pool is a shallow end which was a bonus for us traveling with a child. The beds are very comfortable which is always a huge plus when traveling. The hosts were responsive with any questions that came up. We would happily stay 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.

Picturesque location! Beautiful and peaceful ! Thanks for a lovely getaway! The WiFi was great and perfect for a day of remote working.

Rachel’s carriage house is a charming and beautifully maintained property—just as described and shown in the photos. Even though the weather wasn’t ideal during our stay, we thoroughly enjoyed cozying up and relaxing in the warm, inviting space. One of our favorite features was the natural light streaming through the tall paned windows in the kitchen and dining area, overlooking the garden—a perfect setting for our morning coffee. The carriage house was thoughtfully stocked with everything we needed for a comfortable and restful getaway. It’s clear that Rachel has put a lot of care into creating a welcoming experience for her guests. We truly enjoyed our time in the Berkshires and would happily return!

Lisa’s place was wonderful, and I highly recommend it. She was very responsive to questions, and I appreciated the helpful notes around the house. The space was thoughtfully made dog-friendly, with couch covers that kept things worry-free. The garden was beautiful, and the property offered great outdoor spaces—a back deck, a front grill with seating, and a creekside trail (not fully cleared, but enjoyable). My dog and I loved it. We stayed on the top floor and loved the airy living room with high ceilings and skylights. Lisa’s nature-inspired decor on the desk and fireplace mantle added charm. The bedroom was spacious, and the extra-large bed was incredibly comfortable. The house having three bathrooms was a nice bonus.

Fin is an extremely warm and accommodating host. He goes out of his way to make his guests feel at home. Every time I stay at the Nest there are extra treats and goodies in the kitchen to personalize my arrival. I truly feel like family when I stay here. Fin adds a European bed and breakfast feel to this pristine 5 star retreat.

We stayed at Caroline and Nathaniel’s beautiful home over the winter and celebrated NYE’s. Their house is beautiful and perched on top of the hills overlooking a lake. The view is absolutely stunning in the mornings. The house was well maintained and clean. The hosts were very active in communicating with us where we needed anything or if we needed to be aware of any situations regarding the house. I would definitely stay here again.

Its a lovely airbnb..and a great location so close to many towns. We went to Tanglewood one night and it exceeded our expectations. I only wish we could have stayed longer. And such a gorgeous yard!!

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.

Nicely appointed and updated cottage for a quiet weekend get-away. The hosts think of everything, in terms of supplies, kitchen set-up, and nice decor. I couldn’t find a kitchen item and it was delivered quickly, which was very thoughtful. Bed was super comfy and the a/c window units came in handy! A little bit of road noise during the day, but it’s not bothersome. Wish I’d been there in a season to enjoy the local town beach, which looked nice. Definitely recommend!