Holiday rentals with outdoor seating in Pittsfield

No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.

Erin’s place was absolutely lovely! We really enjoyed the location - so peaceful and conveniently close to Art Omi. The cabin was beautifully maintained, and we especially loved the interior design, which felt both stylish and cozy. We stayed for two nights but honestly wish we could have stayed longer. Highly recommend!

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.

Lawrence and Ilze are great hosts! They actually just live next to the house and they own a farm. We took our kid to visit their farms with lots of beautiful chickens and roosters. My son even has a chance to feed the chickens. We will definitely come back!

Adrian’s place was absolutely lovely. It’s beautiful, peaceful, and easy to relax into. The new “hedge” separating the driveway and the side yard is lovely. Having nature all around is gorgeous and restorative. We’ll definitely return!

Had a wonderful time at Granite ledge. Absolutely beautiful backyard. Very peaceful and comfortable. The bed was very comfortable and we slept like babies. Highly recommend and would definitely stay here again.

Edina and Glen's house was beautiful, spacious, and pristine. It was the perfect setting for a "girls weekend". The grounds were stunning, and made for a great setting. Very close to town, shopping, and wonderful restaurants. We really appreciated that our hosts were very proactive in reaching out and making all instructions clear. They were communicative and flexible. Thank you for having us in your beautiful home! Very memorable weekend.

Beautiful place! Great location and well kept/well maintained house.

Our stay couldn’t have been better. The listing matched reality perfectly—stairs and all—and the hosts stayed a step ahead with friendly, detailed messages and a useful house guide. The location is superb: an easy stroll to everything in North Adams and a great jumping-off point for exploring the Berkshires. The home itself was spotless, cozy, and wonderfully quiet. The hosts were extremely understanding of a minor issue (our fault) that occurred. We thoroughly enjoyed our visit and would gladly return.

Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy

We enjoyed our stay at Tom's place. It was spacious, well appointed and clean. The birds and squirrels in the nearby trees were entertaining. The location was excellent for exploring North Adams on foot and nearby towns/parks. Tom was helpful and responded quickly to all our questions. I would highly recommend staying here.

Easy checkin and the room was pristine. Bed was very comfortable and shower was great. Plenty to do in the area and restaurants were walkable. Many eateries to choose from. Also nearby hiking. Great place to stay.

We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)

Great spot, very well-appointed, with beautiful views. Frank was a great host and I highly recommend.

Brent's place was everything we were looking for! We were hoping to have a cozy base to explore Mt. Greylock, Mass MOCA, and Williamstown, and this spot couldn't have been better. Plus, the property itself was fantastic -- spacious, incredible views, and a wonderful outdoor kitchenette/sitting area. Brent is also a very responsive, very nice host.

Definitely a space with great level of thoughts and details makes you feel comfortable and relaxed. Surrounded by the nature, you can immerse yourself in the beautiful mountain view and bird chirps, very peaceful and tranquil. We saw deers walking by, rabbit hiding in bush from raining, and a little chipmunk busy around the house all the time. Thanks Katey for sharing her beautiful home and being a great host, super responsive and provides lots of useful information. We had an amazing time!

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.

Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.

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!

Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.

We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!

Perfect location to mt snow.. right across the street. It's an older complex but had everything we needed for a few days of skiing.. would rent again

Had an awesome stay here. The place was super clean, really cozy, and exactly what I needed. The host was great—quick to respond and super helpful the whole time. You can tell they put effort into making it a comfortable spot. Would definitely stay again!