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Pet-friendly 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.

SUPERHOST
  1. Entire guesthouse
  2. Lenox
Lenox - Sunny cottage nestled in the garden

Our cottage, nestled next to the garden, is magical. Paul and I have spent many summers there and loved waking up to the birds chirping and watching all that nature has to offer while drinking coffee/tea on the deck. We are located 1.8 miles from Tanglewood and 1/2 mile from the center of town in a quiet residential area.

$80 per night
SUPERHOST
  1. Entire home
  2. Dalton
The Yellow House

The Yellow House in the Berkshires is the perfect place for a getaway, just 2. 5 hours from NYC and 2 hours from Boston. This historic small town offers many activities including Jacob's Pillow, hiking trails, skiing, Mass MoCA, and The Clark Art Institute. It is close to Tanglewood in Lenox and the Norman Rockwell Museum in Stockbridge. Located steps away from The Stationery Factory, which houses a food market, gallery spaces, artisan shops, coffee shop, and the Shire Brewhouse & pub.

$84 per night
SUPERHOST
  1. Entire home
  2. Chester
Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

$159 per night

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Pet-friendly cabins in Berkshire County

SUPERHOST
  1. Entire cabin
  2. Monterey
Secluded cabin with babbling brook
$229 per night
  1. Entire cabin
  2. East Otis
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
$163 per night
  1. Entire cabin
  2. Mill River
'The Mill River Cabin’ w/ Fireplace & River View!
$226 per night
  1. Entire cabin
  2. Becket
Waldtreff - quiet grand cabin
$250 per night
SUPERHOST
  1. Entire cabin
  2. Tolland
Lake View Cabin in the Berkshires
$220 per night
  1. Entire cabin
  2. Canaan
Eagle's Watch Cabin
$97 per night
SUPERHOST
  1. Entire cabin
  2. Canaan
Newly Renovated Cabin in the Country
$325 per night
SUPERHOST
  1. Entire cabin
  2. Sheffield
Large Log Cabin in the Southern Berkshires near GB
$324 per night
SUPERHOST
  1. Entire cabin
  2. North Adams
The Mohawk Cabin @ Wigwam Western Summit
$195 per night
  1. Entire cabin
  2. Stockbridge
Charming Stockbridge Cabin
$378 per night
  1. Entire cabin
  2. Lanesborough
Luxury cabins
$125 per night
SUPERHOST
  1. Entire cabin
  2. North Adams
The Pocumtuck Cabin @ The Wigwam Western Summit
$204 per night