House vacation rentals in West Stockbridge

The lakehouse looks exactly like the photos - stylish and cozy. The house looks small from the outside, but we were amazed by how well it fit our family of seven adults and two toddlers. The instructions/guide to the house was clearly written and super helpful, and Vincent was very easy to communicate with, usually responding right away. We were grateful for all the amenities the house comes with. In addition to enjoying the house itself and the gorgeous deck, we also made smores one night in the fire pit and went kayaking with the little ones. The owner provides guests with bracelets that give access to the community amenities as well. The community pool, playground, and little beach were all beautiful and very well maintained. Our little ones especially loved this weekend!

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!

The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !

Beautiful home! Extremely clean upon arrival and excellent communication. Everything in the house was clearly labeled and directions for check-in and check-out were very clear. Sadly it rained our entire stay so we could not enjoy the pool or the beautiful backyard, but we still had a lovely stay. We hope to come back soon!

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Red Cottage is absolutely beautiful, a great space for a girls' trip! The surroundings are gorgeous, hiking trails are less than 10 mins away, downtown is 15 minutes away, but we spent a lot of time at the house catching up by the fire. The hosts were very responsive and helpful and provided us with tons of recs. We are already looking forward to coming back next year.

The pictures don’t do it justice. A beautiful place for a peaceful retreat. The home is well equipped with everything you might need and more. And the decor! The more you look the more interesting the space gets. We loved our stay.

We had a wonderful time and this house is completely amazing. There is absolutely nothing missing! When Tiffany said, "all you need to bring are clothes" she wasn't joking. The person who designed the house was a genius with the master bedroom on one side of the house, the 2nd bedroom on the other side and the 3rd on the 2nd floor. Privacy inside as well as outside. It was a hiking trip for the family and included Kennedy Park, Olivia Outlook and the Great Monument Mountain. After spending the day hiking, the hot tub, playing pool and watching a movie in the theater just ended a perfect day. We didn't realize how close we were to MA and it was bonus to explore Western Mass as well. Thank you Tiffany for sharing your home with us.

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!

We were happy with this AirBNB and would stay here again. It was nice and quiet but a very short drive into Great Barrington. Close to lots of hiking. Updates have been made since some of the previous reviews. There are two couches in the living room and some of the stock items in the kitchen for convenience.

This was the perfect place to stay while vacationing in the Berkshires. It’s at the end of a quiet cul de sac and centrally-located to most attractions. Annie and Andrew gave very clear instructions and were very communicative before and during our stay. The house was extremely comfortable- my family didn’t complain about anything which is as scarce as hen’s teeth. I would highly recommend staying here!

I had the best stay at Lucas’s beautifully decorated home. The house is warm and inviting, and I felt right at home. The location is quiet and peaceful, surrounded by woods, and located within a beautiful walkable neighborhood perfect for taking my dog on walks. Lucas was very responsive and helpful when I needed to extend my stay a couple extra nights. I can’t say enough good things about this place and host. I’d love to stay here again during warmer months and enjoy the porches and outdoor areas, but it was also very cozy during the cooler weather when I was there. It’s a perfect home away from home.

We had an amazing stay at Bradley’s home. It is a perfect size with everything you need for a relaxing vacation. It is close to so many great restaurants and cute downtown areas for shopping. The beds were super comfortable and the air conditioning worked like a champ. The shower was huge with top notch water pressure. Star of the stay was definitely the hot tub, really strong jets and great temperature control. I did not want to leave at the end of our trip! Thank you Bradley for being a great host and welcoming us into your beautiful home!

We enjoyed our time for a girls weekend at Jill's place. The kitchen is well stocked for a weekend hanging inside to cook and catch up. And the space looks just like the pictures. The hot tub and fire place were great too. Jill is quick to respond to any questions.

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.

One of the cleanest Airbnbs I've stayed in. Perfect for a group of 5 women. Space was great, all had our own bed, and the two bathrooms worked well for us. Minutes to all attractions and restaurants in the Stockbridge/Lenox area. Large, beautiful deck that we wished we had been able to use more but for all the rain. Only thing to note is that if you have mobility issues, the back stairs on the deck to get into the house might be challenging. Other than that, would definitely recommend to others and would stay here again!

This was a perfect vacation home for our family trip. Spacious house with beautiful indoor and outdoor spaces, a well equipped kitchen, luxurious and extremely comfortable furnishings and a location that makes visits to surrounding charming towns so easy.

Nice place. Great layout. Easy to navigate. Host was very communicative. We would stay there again.

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!

Lovely stay! The place was spotless, beautifully decorated, and clearly designed with care. Everything felt thoughtfully chosen, and the amenities were great—comfortable bedding, quality toiletries, and a well-stocked kitchen. Would definitely stay here again!

This lovely, renovated barn is the perfect place to get away.  The space combines chic, sophisticated décor with a homey, comfortable ambiance (including luxurious linen sheets, amazingly comfortable beds and the extravagance of three bathrooms with showers!) The kitchen is well-stocked and there is a charming deck for sitting or eating outside.   The location is ideal, with easy travel to Chatham, Hillsdale, W. Stockbridge or Great Barrington and all the pleasures of both Columbia County and the Berkshires.  Ricky is a gracious host who responded to all questions quickly and with warmth.  All in all, highly recommended!

The house is absolutely perfect for a quiet, rural getaway that's in close proximity to Hudson and Great Barrington! The property is green and lush and there are numerous picture windows to enjoy the surroundings and stunning views. The wood floors and ceilings make the home feel incredibly cozy and there are numerous seating areas and a large kitchen. We had a fantastic time staying and would highly recommend it to anyone!