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Curated homes backed by local expertise and personalized service.
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From cozy cottages to spacious estates, every home is carefully selected for location, comfort, and character.
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Every home is professionally prepared for your arrival with clean linens, quality standards, and dependable support throughout your stay.
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Serving the region since 2005, we connect guests with homes that match the best of the Berkshires — from ski season to summer escapes.
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Reviews
5.0
920 reviews
We spent five wonderful weeks at the Lakeside Cottage in July - and, honestly, we could have stayed another five weeks! The house seamlessly combines the charm of a rustic lake cabin with the modern amenities necessary for a relaxing retreat (the central air conditioning, Smart TVs, excellent WiFi, gas grill and dishwasher were greatly appreciated!) Neil is a friendly, responsive and attentive host without being overbearing. We swam in the lake almost every day and used all the water toys. We especially enjoyed kayaking across the lake to The Cliff House restaurant for dinner and then paddling back under the moonlit sky. Heaven! We highly recommend the Lakeside Cottage and look forward to returning!
Everything I could say about staying at Laurel 11 would still not do it justice. It is an incredible home—warm, welcoming, and full of thoughtful details, with a wonderful connection to nature.<br/>The location of the house is privileged, adding even more value to an already exceptional stay. The house is very clean, and the owner’s attention and hospitality are outstanding. Sarah and Claudia were both incredibly attentive, responsive, and helpful throughout our stay.<br/>Without a doubt, we will be returning to this home next summer.
This place is excellent and exceeded my expectations. The host was proactive and made everything very clear and easy. The house was comfortable, clean, well-equipped, reasonably priced, and in a great location. We’d love to stay here again some time.
Beautiful house and property, great location. The house was even better than the pictures. I would definitely stay here again.
Lovely stay on the lake. The house had all we needed. The four paddle boards were a great bonus. All went smoothly.
The property I think was even more beautiful than the photos! LOVED this house and lawn, screened in porch etc. host was super responsive and very easy to communicate with
Really a great place to stay for a family gathering. This was a beautiful old house with plenty of space to gather and converse or find a quiet spot. The rear yard is fantastic for lawn games. A gem!
Such a beautiful, charming house in a quiet neighborhood. Easy access to downtown Great Barrington. My family thought it was one of the nicest houses we have rented. Every evening, we spent lots of time on the screened front porch enjoying board games, reading or catching up. The house is thoughtfully equipped with everything we needed. We will return!!
When we first checked in and opened the front door, somehow the handle fell off from the inside. We called the caretaker and within the hour he was there to fix the problem. Other than that, everything was perfect from beginning to end for the entire weekend. We loved the house, the backyard, the game room, etc.
Quiet . Peaceful . Lake is beautiful and nice large bass .
We spent five wonderful weeks at the Lakeside Cottage in July - and, honestly, we could have stayed another five weeks! The house seamlessly combines the charm of a rustic lake cabin with the modern amenities necessary for a relaxing retreat (the central air conditioning, Smart TVs, excellent WiFi, gas grill and dishwasher were greatly appreciated!) Neil is a friendly, responsive and attentive host without being overbearing. We swam in the lake almost every day and used all the water toys. We especially enjoyed kayaking across the lake to The Cliff House restaurant for dinner and then paddling back under the moonlit sky. Heaven! We highly recommend the Lakeside Cottage and look forward to returning!
Everything I could say about staying at Laurel 11 would still not do it justice. It is an incredible home—warm, welcoming, and full of thoughtful details, with a wonderful connection to nature.<br/>The location of the house is privileged, adding even more value to an already exceptional stay. The house is very clean, and the owner’s attention and hospitality are outstanding. Sarah and Claudia were both incredibly attentive, responsive, and helpful throughout our stay.<br/>Without a doubt, we will be returning to this home next summer.
This place is excellent and exceeded my expectations. The host was proactive and made everything very clear and easy. The house was comfortable, clean, well-equipped, reasonably priced, and in a great location. We’d love to stay here again some time.
Beautiful house and property, great location. The house was even better than the pictures. I would definitely stay here again.
Lovely stay on the lake. The house had all we needed. The four paddle boards were a great bonus. All went smoothly.
The property I think was even more beautiful than the photos! LOVED this house and lawn, screened in porch etc. host was super responsive and very easy to communicate with
Really a great place to stay for a family gathering. This was a beautiful old house with plenty of space to gather and converse or find a quiet spot. The rear yard is fantastic for lawn games. A gem!
Such a beautiful, charming house in a quiet neighborhood. Easy access to downtown Great Barrington. My family thought it was one of the nicest houses we have rented. Every evening, we spent lots of time on the screened front porch enjoying board games, reading or catching up. The house is thoughtfully equipped with everything we needed. We will return!!
When we first checked in and opened the front door, somehow the handle fell off from the inside. We called the caretaker and within the hour he was there to fix the problem. Other than that, everything was perfect from beginning to end for the entire weekend. We loved the house, the backyard, the game room, etc.
Quiet . Peaceful . Lake is beautiful and nice large bass .
Local expertise since 2005