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Vacation Rentals & Apartments in Berkshires

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Vacation Rentals & Apartments in Berkshires

About Berkshires

172 apartments

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 45 minutes

Price per night from

$249

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Berkshire Home on Lake Garfield w/Dock & Boats

Monterey house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 1 hour 28 minutes

Price per night from

$299

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

Lee house

1 bedroom / 2 bathrooms / sleeps 10

Responds fast! avg. 1 hour 28 minutes

Price per night from

$239

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Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$110

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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

Price per night from

$175

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Waterfront Cottage - 10 Mins to Great Barrington!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 28 minutes

Price per night from

$180

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Charming Room with Private Bath in Colonial Farmho

Tyringham house

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 24 minutes

Price per night from

$249

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Great Vacation House in the Berkshires on Richmond Pond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$186

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Rustic Berkshires Cottage w/ Views of Lake Buel!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 1 hour 28 minutes

Price per night from

$110

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Cozy Jiminy Peak Area Condo w/Patio & Pool Access!

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 8 minutes

Price per night from

$185

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Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$324

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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,

Price per night from

$200

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Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$214

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Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$299

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Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$274

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Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$449

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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

Responds fast! avg. 3 hours 51 minutes

Price per night from

$223

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Shaker Hill

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$374

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Country Elegance in the Berkshires

Great Barrington house

4 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 27 minutes

Price per night from

$648

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Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$125

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Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$225

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Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 45 minutes

Price per night from

$100

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New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$145

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Idyllic Berkshire Home perfect for families or friends with pool and gardens

Richmond house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$499

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"The Barn" on Tower Mountain

Hancock house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$150

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Spacious wooded home

Becket house

4 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$195

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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

Price per night from

$189

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Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$105

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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

Price per night from

$149

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BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$598

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Apartment walking distance to Mass MoCa!!

North Adams apartment

2 bedrooms / 1 bathroom / sleeps 10

Price per night from

$175

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Cill Aodain Cabin

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 19 minutes

Price per night from

$180

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Unique People & Pet-Welcoming Country Haven

Charlemont apartment

1 bedroom / 1 bathroom / sleeps 4

“Cozy little spot, kid and definitely dog friendly” We brought our Cavalier with us and had a great time at the cottage. It was clean and gave us tons of room. Would definitely stay again.

Price per night from

$129

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RiverSong Suite In The Berkshires

North Egremont apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 35 minutes

Price per night from

$189

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3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / sleeps 15

Price per night from

$183

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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 42 minutes

Price per night from

$155

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House On Main Street

Williamstown house

4 bedrooms / 5 bathrooms / sleeps 16

Price per night from

$494

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Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 29 minutes

Price per night from

$195

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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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