Berkshire Rental Properties

Discover the Berkshires

Curated rental properties for every season.

Available properties

EXPERIENCE THE BERKSHIRES

More Than Just a Stay
Curated homes backed by local expertise and personalized service.

Curated Homes for Every Stay

Curated Homes for Every Stay

From cozy cottages to spacious estates, every home is carefully selected for location, comfort, and character.

The Rental-Ready Promise

The Rental-Ready Promise

Every home is professionally prepared for your arrival with clean linens, quality standards, and dependable support throughout your stay.

Your Local Berkshire Experts

Your Local Berkshire Experts

Serving the region since 2005, we connect guests with homes that match the best of the Berkshires — from ski season to summer escapes.

Find Your Perfect Stay

Tailored to your lifestyle

Reviews

5.0

917 reviews

5.0 / 5

Beautiful house and property, great location. The house was even better than the pictures. I would definitely stay here again.

Elisabeth
ElisabethStayed in July 2026
5.0 / 5

Lovely stay on the lake. The house had all we needed. The four paddle boards were a great bonus. All went smoothly.

Elana
ElanaStayed in July 2026
5.0 / 5

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

Marie
MarieStayed in July 2026
5.0 / 5

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!

Kevin
KevinStayed in July 2026
5.0 / 5

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!!

Marese Mary
MareseStayed in July 2026
5.0 / 5

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.

Guido
GuidoStayed in July 2026
5.0 / 5

Quiet . Peaceful . Lake is beautiful and nice large bass .

Nathan
NathanStayed in July 2026
5.0 / 5

Beautiful house, great for a large family or two smaller families! Great location! Hope to be back again next year!

Molly
MollyStayed in July 2026
5.0 / 5

The house had everything we needed and wanted. Would definitely stay there again!!

Marjorie
MarjorieStayed in July 2026
5.0 / 5

The lakeside home was refreshing for my mother, sister, my kids, and her children to stay in the Berkshires. It is very clean and homey. Two bedrooms are small/ not much walking space, so it is best to have only one large suitcase in those rooms or one small one. Stairs going up are narrow, so only good for older children and able bodied adults. My mother stayed in the first floor bedroom, which was perfectly suited for her. It was great to have access to kayaks and swimming mats. The views of the lake are very beautiful and the water was warm for swimming at the end of June.

Crystal
CrystalStayed in July 2026
5.0 / 5

Beautiful house and property, great location. The house was even better than the pictures. I would definitely stay here again.

Elisabeth
ElisabethStayed in July 2026
5.0 / 5

Lovely stay on the lake. The house had all we needed. The four paddle boards were a great bonus. All went smoothly.

Elana
ElanaStayed in July 2026
5.0 / 5

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

Marie
MarieStayed in July 2026
5.0 / 5

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!

Kevin
KevinStayed in July 2026
5.0 / 5

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!!

Marese Mary
MareseStayed in July 2026
5.0 / 5

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.

Guido
GuidoStayed in July 2026
5.0 / 5

Quiet . Peaceful . Lake is beautiful and nice large bass .

Nathan
NathanStayed in July 2026
5.0 / 5

Beautiful house, great for a large family or two smaller families! Great location! Hope to be back again next year!

Molly
MollyStayed in July 2026
5.0 / 5

The house had everything we needed and wanted. Would definitely stay there again!!

Marjorie
MarjorieStayed in July 2026
5.0 / 5

The lakeside home was refreshing for my mother, sister, my kids, and her children to stay in the Berkshires. It is very clean and homey. Two bedrooms are small/ not much walking space, so it is best to have only one large suitcase in those rooms or one small one. Stairs going up are narrow, so only good for older children and able bodied adults. My mother stayed in the first floor bedroom, which was perfectly suited for her. It was great to have access to kayaks and swimming mats. The views of the lake are very beautiful and the water was warm for swimming at the end of June.

Crystal
CrystalStayed in July 2026

Local expertise since 2005

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