House holiday rentals in Lanesborough

My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

We had a great time at Natalia house, a very big house with a lot to do for my three years old daughter. Will definitely stay here again.

What a great spacious home. Plenty of room for the whole family. Clean and neat! Beds were super comfortable! Great water pressure. Beautiful back yard and three season porch. This was our second visit here and it was just as great as the first!!

Such a beautiful winter getaway, my bf and I came here for VDay weekend. We loved the private quiet area for just two of us the space was perfect. Can’t wait to come back in summer to utilize the natural pool.

Loved the house. Kitchen is great. Awesome living room with very comfortable couch and fireplace. Bedrooms perfect. Hot tub was perfect. Original Nintendo system upstairs was fun. Went skiing at Hunter which is 20-25 min away. Woodstock 15 min away. Really a great place. Jaime was responsive, friendly and helpful.

Derek's place is great for a family get together! So many beds/bedrooms and spread out for privacy! There are so many sitting areas throughout the house and a great pool and hot tub area. The backyard is beautiful. It is so peaceful and relaxing there. The owners give you a booklet of the many places to go nearby, which is a great reference. The town of Great Barrington has a wonderful farmer's market and unique stores. So much to look at. Can't wait to go back!!

Really enjoyed our stay. Host is very friendly. House is wonderful and so comfortable. Had a wonderful sleep both nights. Location is very convenient. Quick access to so many restaurants and then 15 minutes to downtown for a game. Would definitely stay here again

Beautiful space for a getaway! We loved the natural light and how beautiful the interior space was! Would love to come back again!!

This house was perfect for our girls’ weekend in Hudson! It was spacious, clean, and had so much character. The location was great—just a short 5-minute drive to Warren Street. We didn’t walk due to the cold weather but it was definitely close and convenient. Would definitely stay here again!

My family and I had a great time. We brought our dog and they are very dog friendly. It’s a great place to get away from city life which is exactly what we were looking got. Hoping to come again soon.

A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

In a world where all airbnbs are starting to look the same, this charming spot stands out like a welcome beacon of light. The decor was thoughtful and felt perfectly in tune with the home and surroundings. We came in the winter-and I can only imagine what their enviable plant collection looks like outside in the summer. You hear the water rushing by and can certainly appreciate the history of this home. The location is so convenient to downtown Hudson and the surrounding area, and is well stocked with anything you might need. There was a snowstorm while we were there and Jeffrey and Juan were amazing at being proactive about snow shoveling so that we could leave in time the next day. They live on property and It's clear they are very passionate about their home and community-as they are eager to share about the home's history, nuances and make suggestions about what you might most enjoy doing in Hudson.

Cute little A-frame cabin! This is our third trip here and it's always a fantastic, memorable experience. Jennifer is super friendly and accommodating. We definitely want to come back soon! :)

Our group of 3 felt right at home! Nice decorator touches - Dash and Albert linens and rugs & lovely soaps added a luxurious feel. We were too busy exploring Hudson to miss the TV, but if that’s important to you, take note. Hosts were super responsive. We can’t wait to return!

A truly cozy and thoughtful retreat. This house anticipated every need. The host created such a welcoming, hygge vibe—perfect for relaxation and feeling at home. I felt truly taken care of during my stay. A peaceful, well-thought-out getaway. (The vinyl ready to go was a lovely detail.)

Our group loved our stay at Emily's & hopes to come back someday during a different season! We were able to very quickly walk or drive to MASS Moca which has a wonderful James Turrell exhibition at the moment. Emily was very proactive with communication & send great local activity & food recommendations. The house itself was even cozier & more spacious than depicted in the photos. It had everything we needed & was immaculately clean when we arrived. We especially enjoyed the vintage bingo game set & record collection. While the weather was colder & rainy, we would have absolutely enjoyed the screened in porch & firepit had the weather been warmer. Hopefully we can take advantage next time! Thank you so much for a wonderful weekend Emily!

Second visit and it was just as nice as the first. We like this house inside and out. The pool and walking trail through the woods are great, and the living room is super comfy for family hanging out at night or on a rainy morning. Highly recommend!

Jason was an amazing host. He did amazing job on the renovations to the house and looked way better in person. His instructions was really great due to the fact that he did a video tour of the house explain what everything did. if we had any questions or concerns, he was there to answer them for us. He was very nice to let us check in early as well. When I told him that we were going to be there an hour early, he said that was completely fine and that we could check in early. If you are wanting to stay somewhere at an excellent price and in the area, would highly recommend staying here!

This was our second time staying at the Hupi House and loved it. House is perfect for 2 families with kids, super comfortable, spacious and cosy, well equipped and lots of things to do in the area. This time we went skiing at the Butternut resort just 10 mins away and was a great experience. Lucas a very friendly and responsive host.

We had an amazing stay at Mitch’s property! Mitch was an incredibly supportive and responsive host, making everything seamless from check-in to checkout. The house itself is beautiful—spacious, peaceful, and perfectly located right off the road while still feeling secluded. We were lucky to experience stunning snowy views during our stay, which made it even more special. The amenities were great, making it an ideal getaway with friends. Highly recommend this place for a relaxing retreat!

Becky’s house was exactly as listed with plenty of space to relax and enjoy the area. Her gardens are beautiful and the house is convenient to the Berkshires without the stress of the downtown areas. We are extremely appreciative of all that was provided!

My partner and I (and our pups) loved our stay at Mian and Anthony’s home! The home was in a perfect location for what we needed, clean and comfortable, and overall great vibe. ✨ Hosts were super friendly and helpful. We would definitely stay again next time we’re in town!

When I first pulled up to Kliment's, I literally teared up - that's how breath-taking his spot is. It was just what the doctor ordered... if doctors actually treated your mind, body, and soul and not just your body :) Seriously though, Kliment's place was an oasis for me: private, quiet, peaceful, with amazing views of the Catskill mountains. His home itself was beautifully decorated, simple yet super cozy, and had everything I needed and then some. (And the chickens were lovely company as well!) Kliment is one of the best Airbnb hosts I have ever had, hands down. With a very hectic schedule, Kliment was flexible, responsive, kind and patient with accommodating my many change requests and needs throughout my stay. Kliment is not just a wonderful host, but also a truly wonderful person - the world needs more people like him. In short: I can't recommend Kliment's home or him as a host enough! If you are hovering over the "Reserve Now" button, book it!!! You won't regret it! :)

An easy and comfortable stay! Their place had everything you might need and they had detailed instructions for anything you might have questions about. Ilze was quick to respond about check in questions and the house is within a 5 min walk of the chief diner and a cool old cemetery. While the weather didn’t cooperate for using the outdoor spaces, the fire pit and deck area were awesome. We didn’t use the downstairs TV area but the upstairs areas were cozy and perfect. Thanks!