Skip to content

Vacation rentals in Berkshire County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Berkshire County

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

Berkshires Rustic Modern Lake Retreat in the Trees
Entire house · 12 guests · 7 beds · 2 baths

Berkshires Rustic Modern Lake Retreat in the Trees2.5 hrs from NYC, 2 hrs from Boston! Escape and unplug in our modern rustic "treehouse"! You'll feel like you are in a secluded forest, but in reality you are 5-30 minutes from anything you would ever want to do in the Berkshires! Two living rooms with gas fireplaces--ideal space for multiple families or groups. Well-stocked kitchen, Fios Wi-fi, Chromecast & seriously comfy beds! Walk to lake, swimming, pool, tennis/pickleball, playground, fitness center, clubhouse, hiking trails, skiing.

Modern Barn with Loft at House on Golden Hill
Barn · 6 guests · 3 beds · 1 bath

Modern Barn with Loft at House on Golden HillFeaturing 35 foot cedar ceilings, large windows, and skylights, The Barn is an oversized two-bedroom apartment with loft at House on Golden Hill, a 1790's farmhouse property in Lenox. The Barn is a detached dwelling with large secluded outdoor space and reserved parking for 3 cars. Situated next to the property's river, the barn provides sweeping mountain views and an idyllic Berkshires experience. Centrally located in the Berkshires and minutes from downtown Lenox and Tanglewood.

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.

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Berkshire County vacation rentals

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

Other great vacation rentals in Berkshire County

SUPERHOST
  1. Entire house
  2. Otis
Charming Cottage with close view of Otis Reservoir
  1. Barn
  2. Lenox
NEW TO AIRBNB! The Granary at House on Golden Hill
  1. Entire guesthouse
  2. Stockbridge
Modern studio with views of the treetops
SUPERHOST
  1. Entire guest suite
  2. Williamstown
Berkshire Guest Suite
  1. Entire apartment
  2. North Adams
A music-lovers apartment in historic North Adams
SUPERHOST
  1. Entire guesthouse
  2. Williamstown
Bright Guest House with Mountain Views
SUPERHOST
  1. Entire cottage
  2. Otis
Peaceful Getaway in the Berkshires
SUPERHOST
  1. Private room
  2. Pittsfield
Equestrian retreat
SUPERHOST
  1. Entire apartment
  2. Sheffield
Hideaway with Spectacular Berkshire Views
SUPERHOST
  1. Entire cottage
  2. West Stockbridge
Cozy Stockbridge Cottage
SUPERHOST
  1. Entire guesthouse
  2. Lenox
Lenox - Sunny cottage nestled in the garden
SUPERHOST
  1. Entire cottage
  2. New Lebanon
The Writer's Cottage