House holiday rentals in 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!

Billy and Rhobin were so helpful and easy to communicate with. The house was so comfortable and peaceful. The property was lovely! 5 Stars all around! Thank you for a fantastic stay!

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

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!

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

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.***

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!

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!

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.

This cabin was an absolute dream come true and exceeded all my expectations! From the moment we arrived, we were enchanted by its charm and the serene beauty of its surroundings. The cabin itself was impeccably clean, cozy, and wonderfully decorated, making us feel instantly at home. Every detail seemed thoughtfully considered, from the comfortable furnishings to the well-equipped kitchen. We particularly loved the personal touches in the decor, i.e. the writing on the walls and all of the books. The location was simply perfect – as a city gal, being surrounded by nature in a peaceful setting was exactly what I was looking for. I enjoyed spending time in the yard in the morning with my breakfast and enjoyed driving to the Norman Rockwell Museum. Taryn was incredibly responsive and helpful with any questions I had and made the entire booking and check-in process seamless. We left feeling completely relaxed, rejuvenated and already have our next stay booked! This place is a true gem!

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 such a lovely country escape for us tired city kids. The pond was a beautiful backdrop for reading and drawing. We brought our binoculars and walked across to Dan B road, spotting gorgeous birds multiple times a day. Our host, Danielle, was extremely responsive and friendly. A fuse blew our second night there, and Danielle had an electrician out to fix it the next day so we could sleep with AC that night. One warning: if you're tall, there are some very low ceilings and doorways. My partner is 6'2 and hit his head repeatedly on the bathrooms' vaulted ceilings and the kitchen doorway. The house would be great for a big group, or a family with kids -- the playroom is delightful and the big, fun kitchen makes you want to fill with your friends and eat and talk for hours. We're very grateful for our quiet getaway there!

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!

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!

We had a great stay! Vinicius’s home was clean, conveniently located to explore the Berkshires and easily accommodated our party of four, plus a dog. The fenced-in yard came in very handy with the latter!

Very rustic, private, peaceful kind of like a camp but with air conditioning and excellent wifi. Bald eagle sat over the lake outside. Kayaks were fun. Tons of great hikes and historical things to see. Town of Great Barrington and Sheffield have great antiquing both high and low end. I would go back any time.

Fabulous location. Lovely, comfortable home. The two relaxation spaces - one off the kitchen and the other being a den - allowed me to read in peace while my husband watched tv. Room airconditioners in both bedrooms and one of the sitting rooms keep all the spaces except the bathrooms cool, and the bathrooms were fine. Susan responded to our one inquiry with lightning speed. One caution: if you are a very light sensitive sleeper, the bedrooms get light as soon as the sun comes up. The downstairs one has a shade for the window and curtains which help, but upstairs one has a bare skylight. We were there over the summer solstice, so the sun was up at 5:30am.

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!

Our stay here was fantastic! The house was beautiful and had everything you could need to feel right at home. Including a kitchen stocked with essentials, lots of fire wood and games. The location of perfect right between Hudson and Great Barrington and it felt super private. Would definitely stay here again.

Perfect location for a few friends that came for a birthday party. Was perfect. I didn’t worry about them at all, and I knew they had a quality stay

This is the second time we’ve stayed here and hope to return again. The house is peaceful and expertly restored. Plenty of screened in doors and windows to let in the breeze. Comfy sofas and beds. Very close to Old Chatham with a cute country store and restaurant or two. Leslie is a helpful and communicative host. The perfect spot for a Hudson Valley getaway.

What an amazing stay. The house is right on a peaceful pond and our kids had the best time exploring every day by canoe. We saw foxes, beavers, tons of birds, and ended each day with s’mores by the fire. Total magic! The house itself was super comfortable and had everything we needed. And the full-size arcade machines were a huge hit with the kids! We’d come back in a heartbeat!