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Vacation Rentals & Apartments in Berkshires

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Vacation Rentals & Apartments in Berkshires

About Berkshires

143 apartments

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$101

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Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$215

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Two weeks in July !!! Last minute cancellation WOW

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$277

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'Butterfly Hill' West Stockbridge Home on 3 Acres!

West Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 39 minutes

Price per night from

$165

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New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 38 minutes

Price per night from

$146

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Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$750

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NEW! Berkshires Cottage w/ Views of Lake Buel!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 21 minutes

Price per night from

$110

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Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and help

Price per night from

$190

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INTERIOR DESIGNERS BOTANICAL GARDENS

Lenox cottage

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$151

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Berkshires House, 40 wooded acres, Lake Frontage

Monterey house

3 bedrooms / 2 bathrooms / sleeps 8

“Nice Family Weekend” We had a very nice family weekend with our only regret being that we couldn't stay longer. Karl quickly greeted us, showed us around, and during the course of our stay left his famous rasberries and maple syrup. We enjoyed hiking

Price per night from

$176

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Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$326

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Berkshire Getaway at 'Tofu'S Retreat'

Alford chateau

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 22 minutes

Price per night from

$334

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Stone School Cottage

Lanesboro cottage

2 bedrooms / 1 bathroom / sleeps 5

“Better than the pictures!” The schoolhouse was so charming, very get away from it all. If you plan to hike Greylock - this is the place to stay! The base parking lot is about 5 minutes away. The schoolhouse is actually on a very quiet road. Cheryl was

Responds fast! avg. 2 hours 28 minutes

Price per night from

$155

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Spacious Berkshires Home w/ Pool & Patio!

North Egremont house

5 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 39 minutes

Price per night from

$700

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Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$276

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Beautiful Vacation Home

Stockbridge house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$499

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PanoramicView1000 sq ft Guest Quarters Berkshires

Hancock cottage

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$146

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Charming and Spacious Colonial Farmhouse on 4 Acre Estate

Tyringham villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 35 minutes

Price per night from

$501

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ground floor garden room

Lee b and b

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 38 minutes

Price per night from

$80

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Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$126

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Berkshire Home on Lake Garfield w/Dock & Boats

Monterey house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 21 minutes

Price per night from

$300

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Country Elegance in the Berkshires

Great Barrington house

4 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 47 minutes

Price per night from

$652

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Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

“beautiful review and wonderful owners.” We stayed here for a weekend with friends and couldn't have asked for a better time. The house is located on a hill above Great Barrington and has access to a lake. Ephrat is perhaps the nicest owner I've ever

Price per night from

$302

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House On Main Street

Williamstown house

4 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$501

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Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms / 2 bathrooms / sleeps 12

“Fantastic place to stay in the Berkshires” Elaine was a very gracious host, and the...accommodations were lovely and in a great location. The historic house has a lot of charm and many nice updates, especially the clean, updated bathrooms and the hug

Price per night from

$276

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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

Price per night from

$220

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Heart of the Berkshires!

Lenox house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$226

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Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 36 minutes

Price per night from

$196

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Cozy Stockbridge Home - Walk To Golf Course!

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 39 minutes

Price per night from

$210

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Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

“Fun and a great value!” We stayed two nights recently at Gartner House and found it to be warm, charming, convenient, and a great value. The bedrooms are cozy, and each is furnished in its own style. The downstairs common areas are perfect for a fam

Price per night from

$201

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Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

Lee apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$379

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

Stockbridge cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 13 minutes

Price per night from

$299

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Berkshire Getaway

North Adams cottage

2 bedrooms / 1 bathroom / sleeps 4

“Peace, quiet and nature are the main attractions to us” We spent a very pleasant weekend in Craig and Val's cottage. If you are looking for R+R, this may be where you should be. It is a very remote quiet area with many attractions and historical sites

Price per night from

$151

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RIVERSONG "PENTHOUSE"

North Egremont room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 35 minutes

Price per night from

$140

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Jiminy Peak Luxury Ski In/Ski Out Home

Hancock condo

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 28 minutes

Price per night from

$390

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Wyndham Bentley Brook at Jiminy Peak

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$252

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Lakefront New Marlborough Cottage - Mins to Skiing

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 21 minutes

Price per night from

$204

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

Hancock hotel apartment

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$456

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Viewing 38 of 143

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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