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Berkshires Rentals

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Berkshires Rentals

135 apartments

Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak

Hancock hotel apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$318

1 / 10

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / Sleeps 7

“Great house to stay in Lenox” We had a great time at Gartner House! The house fits 7 of us comfortably. We attended a wedding at Kemble Inn and it was 3 minutes drive. Convenient location, a few minutes drive to restaurant, we also went to Lee premium

$149

1 / 21

Enchanted Cottage on Babbling Brook

Tyringham house

3 bedrooms / 4 bathrooms / Sleeps 6

$249

1 / 27

Charming 2BR Hancock Condo - Walk to Ski Lifts!

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$184

1 / 26

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / Sleeps 6

“Clean, Comfortable and Convenient” This property is perfect for people with pets. Serene setting with a gorgeous view. The hosts, Tom and Susan, were gracious and very helpful. Highly recommended if your travels take you to Northwest MA.

$144

1 / 16

NEW! 'Butterfly Hill' 2BR West Stockbridge House

West Stockbridge house

2 bedrooms / 2 bathrooms / Sleeps 4

$164

1 / 24

Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage

1 bedroom / 1 bathroom / Sleeps 2

$225

1 / 10

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 6

$198

1 / 23

ROOM walking distance to Mass MoCa

North Adams apartment

1 bedroom / 2 bathrooms / Sleeps 2

$95

1 / 9

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / Sleeps 6

$144

1 / 8

Lakeview cottage with swingset & firepit!

Richmond house

3 bedrooms / 1 bathroom / Sleeps 6

“Great Place for Summer Fun!” A friend and I rented this house in Richmond Shores from June - August in 2008 and 2009. It was the perfect size, perfect location, and greatest part about living in the Berkshires for those two summers. Renting from Dia

$134

1 / 10

Stone School Cottage

Lanesboro cottage

2 bedrooms / 1 bathroom / Sleeps 5

“Lovely” Wonderful relaxing location to get away for a weekend or longer. Cheryl and Rich are excellent hosts. The cottage is perfect and Cheryl and Rich have done an amazing job preserving the history of this little school. Easy drive to many local

$154

1 / 10

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$112

1 / 33

The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / Sleeps 10

$497

1 / 14

Heart of the Berkshires!

Lenox house

3 bedrooms / 1 bathroom / Sleeps 6

$224

1 / 12

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$249

1 / 6

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / Sleeps 4

“Nice and cozy” The cabin was just as we expected. It was clean, comfortable, and had all the necessities we needed. The weather was a bit chilly, so we were not able to check out the lake. We would definitely stay in this cabin again.

$148

1 / 13

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / Sleeps 6

$194

1 / 24

Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$198

1 / 16

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 7

$218

1 / 13

Country Elegance in the Berkshires

Great Barrington house

4 bedrooms / 6 bathrooms / Sleeps 12

$646

1 / 24

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / Sleeps 12

“Wonderful weekend in a wonderful home in Great Barrington” We are a group of 10 that gather from Mass./N.Y./ New Jersey every summer to enjoy all that the Berkshires have to offer. We came upon this gem and could not have been happier. The homeowner

$398

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

Lenox cottage

1 bedroom / 1 bathroom / Sleeps 5

$149

1 / 30

This weekend will be perfect To ski or not to ski! New snow and great temps.

West Stockbridge house

3 bedrooms / 3 bathrooms / Sleeps 8

“Incredible vacation stay or seasonal rental” My family rented this home for an entire summer. The house is beautiful and perfectly suited for any sized family. We stayed with two adults and three children (infant-7yrs old), but also had several occa

$273

1 / 18

Cultural Playground 2 bed, 5 minutes to Tanglewood

Stockbridge cottage

2 bedrooms / 2 bathrooms / Sleeps 6

$298

1 / 25

Berkshires Summer Rental Beaver Pond Hancock MA

Hancock condo

3 bedrooms / 2 bathrooms / Sleeps 6

$100

1 / 13

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / Sleeps 8

$100

1 / 26

Charming and Spacious Colonial Farmhouse on 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / Sleeps 8

$497

1 / 15

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / Sleeps 6

“Great home, great location” Beautiful, modern and cosy home which proved to be a great base for the trip! The fire was an added treat at the end of the day! Location wise the cottage was perfect - close to some wonderful hikes, gorgeous villages and

$100

1 / 8

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / Sleeps 10

$398

1 / 23

chestnut lodge Queens Room

Lee b and b

1 bedroom / 1 bathroom / Sleeps 2

$174

1 / 2

Cill Aodain Cabin

Great Barrington cottage

1 bedroom / 1 bathroom / Sleeps 2

$179

1 / 16

Beautiful New Construction Vacation Home

Stockbridge house

4 bedrooms / 4 bathrooms / Sleeps 12

$496

1 / 32

Wyndham Bentley Brook

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$199

1 / 19

3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / Sleeps 15

$184

1 / 31

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / Sleeps 18

$298

1 / 31

Apartment walking distance to Mass MoCa!!

North Adams apartment

2 bedrooms / 1 bathroom / Sleeps 10

$174

1 / 22

The Smith Farm Homestead

Alford b and b

1 bedroom / 1 bathroom / Sleeps 2

“Beautiful Stress Free Days In The Smith Homestead” The Smith Homestead is a fantastic get-away for those looking to get peace and quiet in the picturesque Berkshire community of alford. The drive up to alford was both easy and relaxing and finding t

$144

1 / 12
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