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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

$320

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NEW! 'Butterfly Hill' 2BR West Stockbridge House

West Stockbridge house

2 bedrooms / 2 bathrooms / Sleeps 4

$165

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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

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Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$250

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Charming 2BR Hancock Condo - Walk to Ski Lifts!

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$185

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Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$199

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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

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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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The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / Sleeps 10

$500

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Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / Sleeps 6

$195

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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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Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / Sleeps 2

$105

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New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / Sleeps 6

$145

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Cultural Playground 2 bed, 5 minutes to Tanglewood

Stockbridge cottage

2 bedrooms / 2 bathrooms / Sleeps 6

$300

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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

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ROOM walking distance to Mass MoCa

North Adams apartment

1 bedroom / 2 bathrooms / Sleeps 2

$95

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3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / Sleeps 15

$185

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

Lee house

5 bedrooms / 6 bathrooms / Sleeps 20

$999

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Apartment walking distance to Mass MoCa!!

North Adams apartment

2 bedrooms / 1 bathroom / Sleeps 10

$175

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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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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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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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Country Elegance in the Berkshires

Great Barrington house

4 bedrooms / 6 bathrooms / Sleeps 12

$650

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Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage

1 bedroom / 1 bathroom / Sleeps 2

$225

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$200

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July4th Berkshires/James Taylor/2Bed Presidential

Lee apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$375

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Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / Sleeps 3

“the cottage description is a perfect fit "romantic getaway in id” We have stayed in many B&B;'s and cottage rentals on the east coast...this experience was one of the best! The owners are exceptional hosts and the accommodations are just as described.

$225

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Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / Sleeps 12

$325

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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.

$149

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Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 7

$219

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Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$112

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Berkshires Summer Rental Beaver Pond Hancock MA

Hancock condo

3 bedrooms / 2 bathrooms / Sleeps 6

$100

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Beautiful New Construction Vacation Home

Stockbridge house

4 bedrooms / 4 bathrooms / Sleeps 12

$499

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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

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Enchanted Cottage on Babbling Brook

Tyringham house

3 bedrooms / 4 bathrooms / Sleeps 6

$250

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Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 6

$199

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Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / Sleeps 8

$100

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Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / Sleeps 6

$215

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