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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

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

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

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

941 reviews

5.0 / 5

Great location, so close to everything we wanted to do and very communicative rental company. The house was kept very clean but it is an older home and some crevices for spiders. Overall it was a great stay. The only negatives were the full bed upstairs was not very comfortable and I wish they had blankets in the house.

Sarah
SarahStayed in September 2026
5.0 / 5

A wonderful home in a beautiful location. The kitchen was very well equipped. We enjoyed eating in the spacious dining room as well as outside on the lovely patio area. Hosts provided everything we needed and more. House was comfortable and immaculate.

Victoria
VictoriaStayed in September 2026
5.0 / 5

We had a blast at the Creamery property! Why? Super comfy spaces to hang out and talk. Beautiful outdoors and a hit tub. Beds were comfortable and bathrooms were clean and well appointed. Home is decorated simply but effectively. Great home for a family or friend get together. Plenty of parking and easy to find. Just a perfect spot for us.

Edith
EdithStayed in September 2026
5.0 / 5

Great weekend! Very cool place

Rebecca
RebeccaStayed in September 2026
5.0 / 5

This was such a wonderful spot for our annual girls trip. Plenty of space for 6 of us. The kitchen had everything we needed. The sunroom was fabulous for drinking our morning coffee and tea. The beds were super comfortable. The location was ideal. The vibe was warm and thoughtful. Highly recommend!

Jenny
JennyStayed in September 2026
5.0 / 5

Beautiful location, lakeside at the end of a road. Wonderful view! Quiet and peaceful. Had everything we needed.

Adele
AdeleStayed in September 2026
5.0 / 5

The house's owner, Tony, was very responsive to the few issues we had with the house. The house was great but is being sold, so won't go into details.

Randall
RandallStayed in September 2026
5.0 / 5

Our family loves this place! We’ve been there twice already and can’t wait to come back next year.

Giselle
GiselleStayed in September 2026
5.0 / 5

We had a wonderful stay! The house was extremely comfortable, perfectly clean, and very well equipped. We truly felt at home. The location is also ideal, just a short walk from Great Barrington. We love this area and absolutely loved the house. We would definitely stay here again!

Jennifer
JenniferStayed in September 2026
5.0 / 5

Amazing property with lake access and kayaks included! Great place to stay

Greg
GregStayed in September 2026
5.0 / 5

Great location, so close to everything we wanted to do and very communicative rental company. The house was kept very clean but it is an older home and some crevices for spiders. Overall it was a great stay. The only negatives were the full bed upstairs was not very comfortable and I wish they had blankets in the house.

Sarah
SarahStayed in September 2026
5.0 / 5

A wonderful home in a beautiful location. The kitchen was very well equipped. We enjoyed eating in the spacious dining room as well as outside on the lovely patio area. Hosts provided everything we needed and more. House was comfortable and immaculate.

Victoria
VictoriaStayed in September 2026
5.0 / 5

We had a blast at the Creamery property! Why? Super comfy spaces to hang out and talk. Beautiful outdoors and a hit tub. Beds were comfortable and bathrooms were clean and well appointed. Home is decorated simply but effectively. Great home for a family or friend get together. Plenty of parking and easy to find. Just a perfect spot for us.

Edith
EdithStayed in September 2026
5.0 / 5

Great weekend! Very cool place

Rebecca
RebeccaStayed in September 2026
5.0 / 5

This was such a wonderful spot for our annual girls trip. Plenty of space for 6 of us. The kitchen had everything we needed. The sunroom was fabulous for drinking our morning coffee and tea. The beds were super comfortable. The location was ideal. The vibe was warm and thoughtful. Highly recommend!

Jenny
JennyStayed in September 2026
5.0 / 5

Beautiful location, lakeside at the end of a road. Wonderful view! Quiet and peaceful. Had everything we needed.

Adele
AdeleStayed in September 2026
5.0 / 5

The house's owner, Tony, was very responsive to the few issues we had with the house. The house was great but is being sold, so won't go into details.

Randall
RandallStayed in September 2026
5.0 / 5

Our family loves this place! We’ve been there twice already and can’t wait to come back next year.

Giselle
GiselleStayed in September 2026
5.0 / 5

We had a wonderful stay! The house was extremely comfortable, perfectly clean, and very well equipped. We truly felt at home. The location is also ideal, just a short walk from Great Barrington. We love this area and absolutely loved the house. We would definitely stay here again!

Jennifer
JenniferStayed in September 2026
5.0 / 5

Amazing property with lake access and kayaks included! Great place to stay

Greg
GregStayed in September 2026

Local expertise since 2005

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