Updating...

Enter dates for more accurate prices

Berkshires Rentals

Filter

Berkshires Rentals

About Berkshires

135 apartments

NEW! 'Butterfly Hill' 2BR West Stockbridge House

West Stockbridge house

2 bedrooms / 2 bathrooms / Sleeps 4

Responds fast! avg. 31 minutes

$165

1 / 24

Charming 2BR Hancock Condo - Walk to Ski Lifts!

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 31 minutes

$185

1 / 26

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / Sleeps 6

$145

1 / 16

Lakefront 2BR New Marlborough Cottage w/Deck

New Marlborough cottage

2 bedrooms / 1 bathroom / Sleeps 4

Responds fast! avg. 25 minutes

$193

1 / 24

Berkshires House, 40 wooded acres, Lake Frontage

Monterey house

3 bedrooms / 2 bathrooms / Sleeps 8

“Quiet and cozy” We really enjoyed our recent stay in Karl's cabin in Monterey, MA. It felt wonderfully removed from the city noises we are used to. It was remote, quiet, and cozy for a day in or a day sitting down by the lake which was only a two minu

$176

1 / 16

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / Sleeps 12

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l

$275

1 / 20

Enchanted Cottage on Babbling Brook

Tyringham house

3 bedrooms / 4 bathrooms / Sleeps 6

$250

1 / 27

Stone School Cottage

Lanesboro cottage

2 bedrooms / 1 bathroom / Sleeps 5

“A wonderful experience” My parents really enjoyed their stay. They said everything was wonderful. It is a very charming and has wonderful history. They really thought the baby horses playing in the field across the street was an over the top touch.

Responds fast! avg. 2 hours 29 minutes

$155

1 / 10

The Smith Farm Homestead

Alford b and b

1 bedroom / 1 bathroom / Sleeps 2

“Visit Great Barrington, but stay in a true New England town. Cho” Set back in the Berkshires, Alford Ma is a stone's throw from New York State. The small town borders Great Barrington, which is rich in activity. Many famous americans have roamed Bar

$145

1 / 12

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

1 / 10

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / Sleeps 4

$200

1 / 6

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

Hancock hotel apartment

2 bedrooms / 2 bathrooms / Sleeps 8

$259

1 / 10

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / Sleeps 6

$145

1 / 8

Historic Home on 8.5 Acres

Dalton house

3 bedrooms / 3 bathrooms / Sleeps 9

$400

1 / 18

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 7

Responds fast! avg. 3 hours 11 minutes

$220

1 / 13

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / Sleeps 12

$325

1 / 10

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / Sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa,

$200

1 / 21

Jiminy Peak Ski Resort-Country Village's Best Unit

Hancock apartment

2 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 46 minutes

$250

1 / 6

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 31 minutes

$215

1 / 30

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / Sleeps 8

$275

1 / 32

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 / 22

Charming and Spacious Colonial Farmhouse on 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 3 hours 5 minutes

$500

1 / 15

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 3 hours 54 minutes

$195

1 / 24

Stockbridge Bowl Lake Beach Cottage near Tanglewood (1.8 miles away)

Stockbridge cottage

2 bedrooms / 2 bathrooms / Sleeps 6

$299

1 / 17

NEW! Berkshires 1BR Cottage w/ Views of Lake Buel!

New Marlborough cottage

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 31 minutes

$110

1 / 23

Beautiful Vacation Home

Stockbridge house

4 bedrooms / 4 bathrooms / Sleeps 12

Responds fast! avg. 3 hours 11 minutes

$499

1 / 32

Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage

1 bedroom / 1 bathroom / Sleeps 2

Responds fast! avg. 3 hours 5 minutes

$225

1 / 10

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

1 / 14

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / Sleeps 8

$112

1 / 33

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / Sleeps 10

$401

1 / 23

Last minute Cancellation! 3 great weeks in August Available. 1 week or all ??

West Stockbridge house

3 bedrooms / 3 bathrooms / Sleeps 8

“A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits

$275

1 / 18

Short Walk to Lake, Peaceful Getaway, Scenic Views

Granville log cabin

3 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 1 hour 14 minutes

$175

1 / 13

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

Lee house

1 bedroom / 2 bathrooms / Sleeps 10

Responds fast! avg. 23 minutes

$241

1 / 24

Apple Cottage

Sheffield farmhouse

3 bedrooms / 6 bathrooms / Sleeps 8

Responds fast! avg. 1 hour 43 minutes

$375

1 / 10

INTERIOR DESIGNERS BOTANICAL GARDENS

Lenox cottage

1 bedroom / 1 bathroom / Sleeps 5

Responds fast! avg. 3 hours 55 minutes

$150

1 / 30

Rustic Rivers end room in the barn at chestnut lodge

Lee barn

1 bedroom / 1 bathroom / Sleeps 4

Responds fast! avg. 2 hours 36 minutes

$156

1 / 6

Lake House in the Berkshires

North Egremont house

3 bedrooms / 2 bathrooms / Sleeps 8

$375

1 / 19
Viewing 38 of 135

About Berkshires

×

A Berkshires getaway in the Berkshire Mountains of Massachusetts is the perfect way to escape the bustle of everyday life and experience breathtaking natural beauty. Get the most out of your time here by staying in a vacation rental, such as a secluded cabin in the woods. Wake up in your vacation rental to the sound of birds and forest life, and enjoy coffee on your private balcony as the sun rises. Then wander downtown to explore the shops, local museums, and unique independent art galleries. In the afternoon, head for the trails to hike to cascading waterfalls, experience a Berkshires zip line adventure, or take an ATV tour. At the end of a busy day, retreat to your home away from home and host a barbeque or a game night for your family and friends.

Here are a few additional suggestions for your trip:

  • Go horseback riding: There are several well-maintained stables in the Berkshires area that offer lessons or guided single and multi-day trail rides.
  • Take a snowmobiling lesson: During the winter, the back country trails through the mountains are perfect for snowmobiling. Take a lesson or join a group adventure.
  • Go skiing or snowshoeing: Cross country skis offer a quieter way to explore the pristine snowy trails and increase opportunities to spot elusive wildlife like foxes and black bears.
  • Go fishing: Take a fly fishing trip along the winding, hidden waterways, or rent a boat and cast your line in the lake at sunrise.
  • Spend an afternoon in the spa: Indulge in a day of pampering at a Berkshires spa with a manicure, pedicure, or hot rock massage.
  • Play golf: Tee off at any one of several champion caliber, emerald green golf courses throughout the Berkshires region.

No matter what activities you have in mind for your vacation or what time of year you plan to visit the Berkshires, you'll find endless things to do here, and the best way to enjoy it all is with your own private vacation rental. Find a cabin or condo that offers all the luxury amenities you and your family need, then relax, unwind, and make great vacation memories. While you're in the Berkshires, you may also want to visit the coast and explore the historic villages of Cape Cod.

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