Updating...

Enter dates for more accurate prices

Berkshires Rentals

Filter

Berkshires Rentals

About Berkshires

123 apartments

NEW! 'Butterfly Hill' 2BR West Stockbridge House

West Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 13 minutes

$165

1 / 24

Charming 2BR Hancock Condo - Walk to Ski Lifts!

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 13 minutes

$185

1 / 26

Two weeks in July !!! Last minute cancellation WOW

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

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

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

$747

1 / 22

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 6

$110

1 / 21

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / sleeps 6

$145

1 / 16

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

$175

1 / 16

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 13 minutes

$215

1 / 30

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

$274

1 / 20

Lakefront 2BR New Marlborough Cottage w/Deck

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 13 minutes

$193

1 / 24

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

$455

1 / 10

RIVERSONG "PENTHOUSE"

North Egremont room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 35 minutes

$139

1 / 32

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

$188

1 / 18

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

$275

1 / 20

NEW! Berkshires Cottage w/ Views of Lake Buel!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 13 minutes

$110

1 / 23

Great Vacation House in the Berkshires on Richmond Pond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

$186

1 / 10

Writer's Room at Chestnut Lodge

Lee b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 56 minutes

$200

1 / 8

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

$374

1 / 12

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

Lee house

1 bedroom / 2 bathrooms / sleeps 10

Responds fast! avg. 13 minutes

$225

1 / 24

The perfect Southern Berkshire winter vacation esc

Sheffield house

4 bedrooms / 2 bathrooms / sleeps 10

$498

1 / 14

Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

$199

1 / 16

Berkshires Summer Rental Beaver Pond Hancock MA

Hancock condo

3 bedrooms / 2 bathrooms / sleeps 6

$100

1 / 13

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

$399

1 / 23

Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

$105

1 / 21

Country Victorian Serenity in the Berkshires

New Marlborough house

4 bedrooms / 2 bathrooms / sleeps 6

$229

1 / 10

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 28 minutes

$155

1 / 10

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

$324

1 / 10

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

“Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything loo

$219

1 / 18

Short Walk to Lake, Peaceful Getaway, Scenic Views

Granville log cabin

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 21 minutes

$175

1 / 13

Berkshire Getaway

North Adams cottage

2 bedrooms / 1 bathroom / sleeps 4

“peace and quiet!” This cottage is in a private, peaceful setting. We very much enjoyed our stay. We spent time at the Mass. Museum of Contemporary art in nearby North adams. We visited the summit of Mount Greylock, which was beautiful. We found our ho

$150

1 / 7

Beautiful Vacation Home

Stockbridge house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 11 minutes

$497

1 / 32

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are b

$299

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

Lenox cottage

1 bedroom / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 59 minutes

$150

1 / 30

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 28 minutes

$219

1 / 13

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are

$149

1 / 13

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

Responds fast! avg. 2 hours 24 minutes

$145

1 / 12
Viewing 38 of 123

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