Berkshire Rental Properties

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Curated rental properties for every season.

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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

930 reviews

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

We had the most amazing stay at Hartfield! The house was comfortable with everything we needed and had so much character.

Ashley
AshleyStayed in August 2026
5.0 / 5

House was as advertised. <br/>The owners have renovated it very well. All new and clean. <br/>Property was as described. <br/>I wish house was closer to lake but great view from windows .<br/>There was everything you could want as advertised. Canoe kayaks fire pit bbq and all you could need inside house . <br/>We enjoyed the week very much. Berkshires have good food many restaurants culture hiking and our favorite place to eat, GB Eats in Great Barrington

Eric
EricStayed in August 2026
5.0 / 5

We had a lovely time here. The location was perfect, the host was easy to reach, and the home was spotlessly clean and really comfortable. Would go back!

Leena
LeenaStayed in August 2026
5.0 / 5

What a stunning location with all the gear for many trips on the lake and awesome, relaxing spots. First class host and location

Clark
ClarkStayed in August 2026
5.0 / 5

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!

Patty & David
PattyStayed in August 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

We had the most amazing stay at Hartfield! The house was comfortable with everything we needed and had so much character.

Ashley
AshleyStayed in August 2026
5.0 / 5

House was as advertised. <br/>The owners have renovated it very well. All new and clean. <br/>Property was as described. <br/>I wish house was closer to lake but great view from windows .<br/>There was everything you could want as advertised. Canoe kayaks fire pit bbq and all you could need inside house . <br/>We enjoyed the week very much. Berkshires have good food many restaurants culture hiking and our favorite place to eat, GB Eats in Great Barrington

Eric
EricStayed in August 2026
5.0 / 5

We had a lovely time here. The location was perfect, the host was easy to reach, and the home was spotlessly clean and really comfortable. Would go back!

Leena
LeenaStayed in August 2026
5.0 / 5

What a stunning location with all the gear for many trips on the lake and awesome, relaxing spots. First class host and location

Clark
ClarkStayed in August 2026
5.0 / 5

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!

Patty & David
PattyStayed in August 2026

Local expertise since 2005

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