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

936 reviews

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

Had a wonderful family weekend. Made use of the canoe and the fire pit. It has a lovely lake view. Kitchen was well equipped for family meals.

Phyllis
PhyllisStayed in August 2026
5.0 / 5

It was an incredible place and all three of us was impressed how cleanit was. Manuel gave us the info we needed for stay. And the kitchen was fantastic- cooking our own meals was a help. Bedrooms- we each had our own, the large bathroom and waher/dryer, walking to town and walking to our art camp on Hollenbeck made this stay very comfortable! Will want to book again when next trip to Great Barrington is planned!

Liz Lindsey
LizStayed in August 2026
5.0 / 5

We very much enjoyed staying here with our family. The lake setting is beautiful. The bathrooms are nicely updated and the kitchen is large and very well stocked with everything you need to prepare meals. The town is just a few minutes drive away. Thank you for an enjoyable stay!

Jennifer
JenniferStayed in August 2026
5.0 / 5

Our stay at Hartfield for a mini family reunion (three generations, including six kids) was magical. The house and property have stories to tell, and there is so much to do in Sheffield and the surrounding area that no one need ever be bored. We enjoyed having the piano for sing-alongs, and the kids were outside for hours looking for salamanders. The kitchen and pantry are well supplied, which was helpful as we celebrated a birthday with a special meal. Beds were comfortable (all on the second floor, fyi for those with mobility limits). There were multiple common rooms and porches with ample space to spread out. It’s a peaceful spot, and we’d love to return in any season. We all imagined it would be quite cozy in winter; we all loved the many, many books and art pieces. The caretaker and management company were friendly and easy to reach, and the caretaker shared interesting local history with us — a bonus!

Jessica
JessicaStayed in August 2026
5.0 / 5

This was our second summer stay at the beautiful Sweetwater home on Lake Buel. My family and I had a wonderful time, the location is so peaceful and view couldn’t be more beautiful, close to Great Barrington and all that the Berkshires has to offer. Hope to be back again!

Alison
AlisonStayed in August 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

Had a wonderful family weekend. Made use of the canoe and the fire pit. It has a lovely lake view. Kitchen was well equipped for family meals.

Phyllis
PhyllisStayed in August 2026
5.0 / 5

It was an incredible place and all three of us was impressed how cleanit was. Manuel gave us the info we needed for stay. And the kitchen was fantastic- cooking our own meals was a help. Bedrooms- we each had our own, the large bathroom and waher/dryer, walking to town and walking to our art camp on Hollenbeck made this stay very comfortable! Will want to book again when next trip to Great Barrington is planned!

Liz Lindsey
LizStayed in August 2026
5.0 / 5

We very much enjoyed staying here with our family. The lake setting is beautiful. The bathrooms are nicely updated and the kitchen is large and very well stocked with everything you need to prepare meals. The town is just a few minutes drive away. Thank you for an enjoyable stay!

Jennifer
JenniferStayed in August 2026
5.0 / 5

Our stay at Hartfield for a mini family reunion (three generations, including six kids) was magical. The house and property have stories to tell, and there is so much to do in Sheffield and the surrounding area that no one need ever be bored. We enjoyed having the piano for sing-alongs, and the kids were outside for hours looking for salamanders. The kitchen and pantry are well supplied, which was helpful as we celebrated a birthday with a special meal. Beds were comfortable (all on the second floor, fyi for those with mobility limits). There were multiple common rooms and porches with ample space to spread out. It’s a peaceful spot, and we’d love to return in any season. We all imagined it would be quite cozy in winter; we all loved the many, many books and art pieces. The caretaker and management company were friendly and easy to reach, and the caretaker shared interesting local history with us — a bonus!

Jessica
JessicaStayed in August 2026
5.0 / 5

This was our second summer stay at the beautiful Sweetwater home on Lake Buel. My family and I had a wonderful time, the location is so peaceful and view couldn’t be more beautiful, close to Great Barrington and all that the Berkshires has to offer. Hope to be back again!

Alison
AlisonStayed in August 2026

Local expertise since 2005

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