Holiday rentals with a patio in Pittsfield

The room was beautiful and it was such a cozy space. The kitchen was great, and I loved the bathroom! the pictures don't do it justice. It was so nice staying there, we were even considering extending out stay.

We enjoy old houses, so we found Emily's house a gem. It is a beautifully renovated space that includes modern conveniences but leaves the beautiful old doors and floors to give depth and beauty to the space.

We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

was communicative and friendly! Cute place and comfortable bed :)

Really clean and perfect for what we needed it for! We were there to move out our daughter from Williams College and it worked out perfectly.

We will never stay at a hotel again. For the price of a hotel we stayed in a cozy one bedroom apartment that was perfect for two. Bed was comfortable. We watched Netflix after seeing a show to wind down, and with one of us being a night owl and one being an early bird it gave us the space to relax without disturbing the other. We asked for a fan when we arrived as my husband liked a breeze and the owner delivered one very quickly. Highly recommend.

Jenna’s place worked well for our family reunion in Catskill village, convenient to Main Street shops. The shower set up (curtain in a tub) was a bit tricky.

Beautiful environment and super welcoming hosts. A great experience!

This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.

We only stayed one evening but found the living space to be perfectly laid out and spotless. The kitchen is fully stocked with about every utensil and appliance you can think of. We especially enjoyed the fresh eggs, treats, and flowers that welcomed us! The living room was especially comfortable. The unit is attached to the rear of the main house but it’s kept totally private. There aren’t many places to eat in Richmond — after all, it is pretty rural— but Stockbridge and Lennox offer many dining options.

We had a wonderful stay at James and Lissy’s house! It was perfectly located for getting around the Berkshires. The house was clean, beautiful, and cozy. When we needed to communicate with James and Lissy they were incredibly responsive and helpful. Every year, my friends from high school and I meet up for a reunion in the Berkshires (we have been doing this annually), and the hope is to stay in this very Airbnb next year, if possible/ available! It was an exceptional Airbnb experience!

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

What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!

Leslie's house was wonderful. Comfortable home with lots of space in a peaceful setting. Beautiful views and walking distance to a bird sanctuary with nice trails. We would love to stay here again.

Our company stayed at Deborah and Ashley’s for 10 days and we had a wonderful stay. We were incredibly comfortable and there was enough room in the house to find separate work space as well. Highly recommended would stay again and D and A were fantastic at communication. 5+!

Great stay here with 5 adults and a teenager. Plenty of room to be together or spread out. It has one of the best equipped kitchens ever! The location is perfect for skiing atJiminey, Bosquet or Catamount. Lots of options to pick from and plenty of good food in the area. Exceptionally clean place and very comfortable beds. Would stay again!

Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.

This place is so welcoming and tasteful. Lots of in-house activities for the evening, when it's raining, or just when you feel like staying in. An easy recommendation.

Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

Ashley has a great place!! It was a fantastic place to visit with my friends and reminisce. Weirdly, this rental turns out to be the place my great grandparents lived and did business as my grandma grew up. I did not have any ghostly contact with my relatives in the apartment (I was kind of hoping and not hoping to see them 😂), but I still had such a meaningful time sitting in the spaces they did so many years ago. Ashley is an excellent host and I will come here again next time I “come home”. 😊

Excellent location and central to all things fun in southern Vermont. Loved the sports center amenities. Very peaceful considering it was end of mud season and not busy at all. We used the pool, workout facilities and locker room. Even had a fireplace we could use ! Christine was incredibly responsive and welcoming. Would recommend to others and would stay again if in the area.

Our stay was excellent. Felt at home. Much recommended.

Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!