Holiday rentals with outdoor seating in West Stockbridge

Beautiful home in a peaceful setting a short drive to Berkshires attractions. The house was cozy and inviting, with so many beautiful touches that made it feel like a real home instead of an Airbnb that was solely designed for income. Despite the size and many nooks and crannies it was impeccably clean. We were there during some chilly rainy days and it was a lovely place to curl up and read or chat, with plenty of room to spread out. One thing to be aware of, the full bath with shower is on the main level, so using it requires toting shower things up and down the stairs each time. Something to be aware of if there's a group member with less mobility. Very doable with assistance, and the shower is a walk-in which was great. I didn't think anyone in my party would mind the train. Little did I know it would turn out to be the highlight of the trip and best part of the stay. Everyone loved it!

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.

Alfredo's home was more peaceful than the photos could show. it was quiet, secluded and clean, inside and out. being close to stores and the town while having the feeling you're farther away from society was just what was needed for the stay.

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!

Great location with easy access to Great Barrington and other Berkshire destinations. Perfect house for families or larger groups, we had everything we needed with various sleeping arrangements. Nice open kitchen and decks. We would be happy to return.

For our fourth stay at Katie and Greg's, we were just as satisfied as the first x3 trips! And we're already planning our 5th! Truly a gem of a home and wonderful hosts. Highly recommend!

I had a wonderful long stay at the Sawmill. It’s a unique spot in a great location. Just a couple minutes to some cute restaurants and shopping in New Lebanon and only about 15 minutes to either Pittsfield, MA or Chatham, NY. It’s very roomy and comfortable. The hosts were very friendly and welcoming. The house was well provided. Everything I could think of, whether it was in the kitchen, bathroom or recommendations and reading material was close at hand. Only wish I could’ve stayed longer.

This was our second time staying in this home. Mark was a great host. His home is beautifully decorated and well maintained. The beds are comfortable and there is plenty of room to spread out. It is located on an amazing piece of forested property that is stunning. Mark was very responsive and went out of his way to our stay great. This is wonderful place to stay.

Loved this little apartment. It has everything you need and more.

Fantastisch!! Charming, comfortable, quite and close in. Love this old house with beautiful woodwork, kousa dogwoods in full bloom in the yard. Great stocked kitchen, although we ate out at the many yummy cafes and restaurants. Mooncloud was a favorite! Comfy, spacious living room. Nice large dining table. Trice was a wonderful host, quick to respond and let us enjoy our space! I am so glad I took a chance on airbnb again - this was one of my favorite stays on airbnb and my favorite in Great Barrington! Would definitely book again!

Went for a Berkshire School reunion the two of us, perfect spot. Charming quiet grounds, perfect location for accessing Berkshire School, clean, Keurig, comfortable bed, amenities as stated (and quick confirmations from host), super easy process for check in and check out. Asked many questions and host responded very quickly and was very friendly in her communications.

Wonderful stay! Beautiful home and so much to do in the area. We had a great time!

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 :)

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!

I’ve visited many, many AirBNB’s over the years and Elisabeth and Ricky’s was one of the best. The accommodation is beautiful, it’s a lovely little converted flat above the garage, settled into the woods and garden. We were greeted by their corgi and by Elisabeth who both made us feel at home. We were able to wander their gardens, drink gin and tonics in the sun and generally make ourselves at home. A lovely couple and a highly recommended Airbnb.

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.

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!

Perfectly set up and spotless. The unit is supplied with everything you could possibly need. By far the best organized, supplied and clean Airbnb we have ever stayed in.

This is my second stay at Daniel’s, and it was just as good as the first! I love the location of his place in relation to the mountain. It’s a quick walk up the parking lot to the trails/lifts. Most importantly, my pups feel right at home, and they know his place now! His home is always clean and the linens/towels always smell fresh! I told him I will be coming back multiple times throughout the snow season to go boarding. He is very responsive and helpful and would go out of his way if need be! Overall, 12/10 recommend Daniel’s spot!

A beautiful home. Felt comfortable and relaxing. Very well equipped. A nice small outdoor seating area to watch the creek and see wildlife.

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!!!

5 stars, 5 stars, 5 stars!! I would just like to say I’ve stayed in many Air B&Bs before, and this one is by far one of my favorites. The hosts are absolutely amazing. They are proactive in responding and really want you be be comfortable and making sure you have no issues. The price was 100% worth it. I love that they included board games as a part of the space, such a nice touch. The bathrooms and bedrooms were also so clean, and we enjoyed our stay. You can really tell the hosts put a lot of love and care into this place. I can’t say enough good things about them!