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Berkshires Rentals

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Berkshires Rentals

135 apartments

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

$150

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Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$199

1 / 16

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$250

1 / 6

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 6

$199

1 / 23

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

Hancock hotel apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$318

1 / 10

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.

$145

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NEW! 'Butterfly Hill' 2BR West Stockbridge House

West Stockbridge house

2 bedrooms / 2 bathrooms / Sleeps 4

$165

1 / 24

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$112

1 / 33

Charming 2BR Hancock Condo - Walk to Ski Lifts!

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$185

1 / 26

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 7

$218

1 / 13

Cultural Playground 2 bed, 5 minutes to Tanglewood

Stockbridge cottage

2 bedrooms / 2 bathrooms / Sleeps 6

$300

1 / 25

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

$400

1 / 30

ROOM walking distance to Mass MoCa

North Adams apartment

1 bedroom / 2 bathrooms / Sleeps 2

$95

1 / 9

Jacob's Tanglewood Ranch (great for groups 10+)

Lee house

5 bedrooms / 6 bathrooms / Sleeps 20

$999

1 / 47

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

$155

1 / 10

Writer's Room at Chestnut Lodge

Lee b and b

1 bedroom / 1 bathroom / Sleeps 2

$199

1 / 8

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / Sleeps 6

$194

1 / 24

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / Sleeps 6

$100

1 / 5

Beautiful New Construction Vacation Home

Stockbridge house

4 bedrooms / 4 bathrooms / Sleeps 12

$499

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chestnut lodge Queens Room

Lee b and b

1 bedroom / 1 bathroom / Sleeps 2

$175

1 / 2

Heart of the Berkshires!

Lenox house

3 bedrooms / 1 bathroom / Sleeps 6

$225

1 / 12

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / Sleeps 12

$323

1 / 10

Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage

1 bedroom / 1 bathroom / Sleeps 2

$225

1 / 10

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / Sleeps 8

$100

1 / 26

Cozy and clean in Gt Barrington- 1 week in summer!

Great Barrington house

2 bedrooms / 2 bathrooms / Sleeps 4

“Easy, comfortable summer getaway!” My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the lake, the bedrooms were airy with cro

$195

1 / 10

Charming and Spacious Colonial Farmhouse on 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / Sleeps 8

$500

1 / 15

July4th Berkshires/James Taylor/2Bed Presidential

Lee apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$375

1 / 12

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / Sleeps 6

$145

1 / 8

Rustic Rivers end room in the barn at chestnut lodge

Lee barn

1 bedroom / 1 bathroom / Sleeps 4

$155

1 / 6

Country Elegance in the Berkshires

Great Barrington house

4 bedrooms / 6 bathrooms / Sleeps 12

$650

1 / 24

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

$145

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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

$275

1 / 18

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / Sleeps 4

$200

1 / 6

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / Sleeps 12

“October in Berkshires” Great location near major attractions such as Tanglewood. Screened porch is great for pre dinner get together. Old house but well maintained except for old house smell. Plenty of room for 6 people.

$260

1 / 20

3BR Lee House w/ Easy Access to Main Street!

Lee house

1 bedroom / 2 bathrooms / Sleeps 10

$235

1 / 24

$199

1 / 12

2200sf Country House on 16 Acres-2 Miles to Jiminy

Hancock house

4 bedrooms / 2 bathrooms / Sleeps 9

“Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope

$225

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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

$135

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