Updating...

Enter dates for more accurate prices

Berkshires Rentals

Filter

Berkshires Rentals

135 rentals

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

Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$198

1 / 16

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

Hancock hotel apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$318

1 / 10

NEW! 'Butterfly Hill' 2BR West Stockbridge House

West Stockbridge house

2 bedrooms / 2 bathrooms / Sleeps 4

$165

1 / 24

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / Sleeps 6

$194

1 / 24

Heart of the Berkshires!

Lenox house

3 bedrooms / 1 bathroom / Sleeps 6

$224

1 / 12

Wyndham Bentley Brook Resort ~ 2 Bedroom, Sleeps 6

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 6

$198

1 / 23

Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage

1 bedroom / 1 bathroom / Sleeps 2

$224

1 / 10

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

$203

1 / 12

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

Enchanted Cottage on Babbling Brook

Tyringham house

3 bedrooms / 4 bathrooms / Sleeps 6

$249

1 / 27

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

3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / Sleeps 15

$184

1 / 31

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / Sleeps 8

$100

1 / 26

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 7

$218

1 / 13

Apartment walking distance to Mass MoCa!!

North Adams apartment

2 bedrooms / 1 bathroom / Sleeps 10

$174

1 / 22

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / Sleeps 6

$215

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

Lenox cottage

1 bedroom / 1 bathroom / Sleeps 5

$149

1 / 30

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$249

1 / 6

Lake House in the Berkshires

North Egremont house

3 bedrooms / 2 bathrooms / Sleeps 8

$373

1 / 19

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.

$146

1 / 16

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

$136

1 / 10

Cultural Playground 2 bed, 5 minutes to Tanglewood

Stockbridge cottage

2 bedrooms / 2 bathrooms / Sleeps 6

$298

1 / 25

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / Sleeps 6

$418

1 / 24

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / Sleeps 6

$144

1 / 8

Cill Aodain Cabin

Great Barrington cottage

1 bedroom / 1 bathroom / Sleeps 2

$179

1 / 16

July4th Berkshires/James Taylor/2Bed Presidential

Lee apartment

2 bedrooms / 2 bathrooms / Sleeps 6

$378

1 / 12

ROOM walking distance to Mass MoCa

North Adams apartment

1 bedroom / 2 bathrooms / Sleeps 2

$95

1 / 9

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

Lee house

1 bedroom / 2 bathrooms / Sleeps 10

$235

1 / 24

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / Sleeps 12

$323

1 / 10

Short Walk to Lake, Peaceful Getaway, Scenic Views

Granville log cabin

3 bedrooms / 2 bathrooms / Sleeps 6

$169

1 / 13

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / Sleeps 8

$273

1 / 32

Perfect Getaway for Body, Mind and Soul

Lee cottage

3 bedrooms / 2 bathrooms / Sleeps 5

“Fantastic home in an absolutely perfect location” I didn't want to leave. It was the most relaxing and tranquil time I could have imagined. The house is lovely and extremely comfortable -- clean, cozy and situated close to a stunning lake. Spent most

$235

1 / 24

Berkshires Summer Rental Beaver Pond Hancock MA

Hancock condo

3 bedrooms / 2 bathrooms / Sleeps 6

$100

1 / 13

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.

$259

1 / 20

Beautiful New Construction Vacation Home

Stockbridge house

4 bedrooms / 4 bathrooms / Sleeps 12

$496

1 / 32
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more