House holiday rentals in Great Barrington

This house was perfect for our needs. We were in town for Berkshires graduation. It was 15 min from the school and 15 min from Great Barrington. Wish the weather would have been better for the pool! They were very available for any of our questions and needs. Definitely recommend!

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

It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

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.***

Stayed here with three others for work. The house was clean and well updated. We had no issues and will look to stay here again.

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!

This property is beautiful! The house and amenities are actually just as nice in real and every detail was so thought out. Arp really has good taste and communicated well throughout our stay.

Stayed at Amal's house with friends for a college reunion. Location was perfect for our needs, quiet, with great view, nature and lake access. Saw deer, geese, chipmunks. Tried to beware of bears, but never saw any. Lovely, luxurious, gorgeous, well-lit, clean and modern house, well fitted-out kitchen (even had ziploc bags), comfortable beds. Hosts were communicative and friendly. Absolutely would stay here again the next time the group of us are in the area.

We had a wonderful, restful stay in this beautiful home. The ambience is so peaceful and the home is spotless, with many thoughtful touches for guests. We'd definitely stay again!

My friends, family, and I have been coming to Great Barrington for more than 20 years. This is the most comfortable home we have stayed in. Everything was as described in the listing. The grounds are also very nice. The house has a beautiful yard, garden, and peaceful atmosphere. Everyone in our group remarked on the comfort, cleanliness, and good energy in the home.

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.

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!

Great stay! This is our second time staying at Bradley’s place and it was exactly the same as last time, in a good way. Place was clean, great neighborhood, very quiet!

Such a perfect house and a perfect stay! We did a midweek stay just to relax and couldn’t have had a better place to do so! The house is beautiful and so clean. The kitchen and everything you need to cook or grill (or make cheeseboards which is what we did). It’s super private and quiet and the back porch is the best. We loved having coffee on the porch every morning. Very close to downtown GB and plenty to do and see! Clear instructions and details about everything in the house and we got to check-in a little bit early. Hope to stay again!

We had an incredible stay. The owner was extremely responsive and checked in on us to make sure everything was ok. The house was very comfortable with a great kitchen and outdoor space.

We stayed for a ski weekend and found the house perfect fit for a group 3 kids skiing and snowboarding. There’s plenty of room in the kitchen in the living room all all we came away extremely satisfied.

Great place for a family walking distance to downtown great barrington but still quiet. Fenced in backyard is beautiful and nice for a dog.

We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).

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.

A beautiful, comfortable house right on the Hudson with stunning views. We loved watching all the life on the river, herons and loons and ducks, as well as boats from tiny crafts to massive barges. There are great hikes just a short distance away. It is a perfect place to rest, write, draw, and make music.

Karen was an excellent host, she had an open line of communication with me. she gave me a list of places in the area for our group to do early in which was helpful in our planning! Very responsive which made it very easy for me to reach out to her. The house was beautiful and amazing. We had rainy weather and this was a perfect stay still because of the pool table, the piano, the large TV in the living room. Kitchen is stocked with plenty of items for eating and cooking. The house location is excellent, you feel like you have privacy but you're still close to the center of town. If I am back in the area, Karen's house is the first place I'm checking!

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!

We had a wonderful 5 night stay at this large home in Great Barrington. The house is close to downtown Great Barrington and all Berkshire activities. The home is beautifully updated and decorated. We especially loved the kitchen which has all top of the line appliances. We also enjoyed the beautiful wrap around porch as well as the fire pit. Any time we had a question, we received an answer promptly from Shannon. Highly recommend!