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Vacation rentals in Berkshire County

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Top-rated vacation rentals in Berkshire County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Modern barn in the heart of the Berkshires
Entire guesthouse · 5 guests · 2 beds · 1 bath

Modern barn in the heart of the BerkshiresModern, renovated, historic dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature. In the fall, pick your own apples and pears from the trees in the back yard.

Berkshire Mountain Views
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath

Berkshire Mountain ViewsRecently built 500 square-foot one bedroom apartment with separate entrance. Kitchenette. Private screened-in porch overlooking Jug End State Reservation, Mt. Everett and the back of Catamount Ski Area. Three miles from Berkshire School, five miles from the center of Great Barrington and .3 miles from the Appalachian Trail. Queen bed in bedroom; can sleep additional two in living area on sectional sofas. Electric fireplace. Mudroom perfect for storing hiking and ski gear. Very quiet.

North Adams-  Spacious Bedroom with private bath
Private room · 2 guests · 1 bed · 1 private bath

North Adams- Spacious Bedroom with private bathSpacious, comfortable room with a queen size bed in a quiet neighborhood. 3/10 mile to Mass MOCA. Parking, separate entrance, private bathroom, microwave, refrigerator, coffee maker, toaster.

Vacation rentals for every style

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Popular amenities for Berkshire County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Berkshire County

  1. Entire guesthouse
  2. Lee
Cozy Guesthouse Near Downtown, Lee
$150 per night
  1. Barn
  2. Lenox
The Granary at House on Golden Hill
$144 per night
SUPERHOST
  1. Entire guest suite
  2. Williamstown
Berkshire Guest Suite
$70 per night
SUPERHOST
  1. Entire guest suite
  2. Lenox
T’Other House
$130 per night
SUPERHOST
  1. Entire cottage
  2. Hinsdale
Cozy Cottage in the Berkshires
$159 per night
  1. Entire cabin
  2. Sandisfield
Berkshires Cabin in Woods with Mountain Views
$350 per night
  1. Barn
  2. Lenox
Modern Barn with Loft at House on Golden Hill
$178 per night
SUPERHOST
  1. Entire guesthouse
  2. Williamstown
Bright Guest House with Mountain Views
$150 per night
  1. Entire apartment
  2. North Adams
Chase Hill Estate: Private Hideaway Small Mansion
$121 per night
SUPERHOST
  1. Entire house
  2. Chester
Riverfront Getaway
$135 per night
SUPERHOST
  1. Tent
  2. Worthington
Cozy Hilltop Bell Tent on Picturesque Farm
$134 per night
SUPERHOST
  1. Entire guest suite
  2. Lenox
"Mozart Room" in Lenox. Hotel style separate space
$121 per night

Top-rated things to do in Berkshire County

Unique activities hosted by local experts vetted for quality