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Berkshires Rentals

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Berkshires Rentals

About Berkshires

123 apartments

$185

Charming 2BR Hancock Condo - Walk to Ski Lifts!

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 21 minutes

$185

1 / 26

$144

PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / sleeps 6

$144

1 / 16

$165

NEW! 'Butterfly Hill' 2BR West Stockbridge House

West Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 21 minutes

$165

1 / 24

$175

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

$225

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

Lee house

1 bedroom / 2 bathrooms / sleeps 10

Responds fast! avg. 16 minutes

$225

1 / 24

$455

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

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

$455

1 / 10

$199

Berkshires Vacation Rental - Bentley Brook Resort Suite

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

$199

1 / 16

$155

Rustic Rivers end room in the barn at chestnut lodge

Lee barn

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 56 minutes

$155

1 / 6

$150

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

$200

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

$200

1 / 6

$250

Wyndham Bentley Brook at Jiminy Peak

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 6

$250

1 / 21

$299

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

Stockbridge cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 15 minutes

$299

1 / 17

$372

Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

$372

1 / 12

$149

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

$275

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

$273

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

$273

1 / 20

$215

Tranquil 3BR Stockbridge House w/Private Deck

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 16 minutes

$215

1 / 30

$400

Historic Home on 8.5 Acres

Dalton house

3 bedrooms / 3 bathrooms / sleeps 9

$400

1 / 18

$110

NEW! Berkshires Cottage w/ Views of Lake Buel!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 21 minutes

$110

1 / 23

$186

Great Vacation House in the Berkshires on Richmond Pond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

$186

1 / 10

$325

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

$325

1 / 10

$225

Romantic Berkshire Cottage on Storybook Estate

Tyringham cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 3 hours 7 minutes

$225

1 / 10

$112

Wyndham Bentley Brook Resort

Hancock condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 58 minutes

$112

1 / 33

$110

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 6

$110

1 / 21

$219

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

$214

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

$214

1 / 17

$225

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

$105

Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

$105

1 / 21

$188

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

$188

1 / 18

$210

NEW! 2BR Stockbridge Home - Walk To Golf Course!

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 21 minutes

$210

1 / 24

$200

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

$250

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 45 minutes

$250

1 / 5

$179

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

$179

1 / 12

$499

Beautiful Vacation Home

Stockbridge house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 3 hours 11 minutes

$499

1 / 32

$285

Family-friendly Cottage Near Lake, Tanglewood

Stockbridge cottage

3 bedrooms / 2 bathrooms / sleeps 7

$285

1 / 16

$193

Lakefront 2BR New Marlborough Cottage w/Deck

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 21 minutes

$193

1 / 24

$145

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

$145

1 / 8

$100

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

$100

1 / 26
Viewing 38 of 123

About Berkshires

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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.

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