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Holiday rentals in Berkshire County

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Top-rated holiday rentals in Berkshire County

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

Silo Suite with Berkshire Mountain Views!
SUPERHOST
Barn · 2 guests · 1 bathroom
Silo Suite with Berkshire Mountain Views!Looking for the perfect destination for a romantic getaway in the Berkshires? Look no further as the Silo Suite at Bloom Meadows is the place for you. With a king bed, fireplace, kitchenette, 3/4 bath, the suite offers everything you need. However, the real beauty is the view of the rolling Berkshire hills off the deck of the silo!
Riverfront Getaway
SUPERHOST
Entire residential home · 4 guests · 2 beds · 1 bathroom
Riverfront GetawayOur 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!
Enchanted Tiny Tower at Santarella Gardens
SUPERHOST
Tiny house · 2 guests · 1 bed · 1 bathroom
Enchanted Tiny Tower at Santarella GardensWhimsical and romantic tower on the Santarella Estate in the Berkshires, Western Massachusetts. This two-story unique, tiny home offers a charming upstairs bedchamber with canopied bed providing amazing views of sky and trees all the way out to the lily pond through massive, mill windows. Downstairs sitting room looks out on the babbling brook. Kitchenette is equipped with Ninja Foodi and microwave for nights in. Guests can spend the day enjoying the grounds or exploring the Berkshires.

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Popular amenities for Berkshire County holiday rentals

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

Other great holiday rentals in Berkshire County

  1. Entire chalet
  2. Averill Park
A Hidden Sparrow
₹29,608 per night
  1. Entire residential home
  2. Cheshire
Berkshire County modern home + pool
₹28,377 per night
SUPERHOST
  1. Entire cottage
  2. Great Barrington
Artist Cottage at the Foot of Monument Mountain
₹15,794 per night
SUPERHOST
  1. Entire cottage
  2. Otis
Peaceful Getaway in the Berkshires
₹14,456 per night
SUPERHOST
  1. Entire guest house
  2. Lenox
The Granary at House on Golden Hill
₹10,794 per night
SUPERHOST
  1. Entire rental unit
  2. North Adams
Steps to MoCA: Large 2 Bd in an historic estate
₹6,736 per night
  1. Entire residential home
  2. Great Barrington
Morgan's Millhouse (Back)
₹7,324 per night
  1. Entire residential home
  2. Egremont
Modern and Stylish Country Lakeside Cottage
₹21,245 per night
  1. Entire residential home
  2. Pittsfield
Berkshire Getaway Ranch 2 bd/2 bth 3 acres + pool
₹31,108 per night
SUPERHOST
  1. Tower
  2. Lee
Fairytale Treehouse Turret at Santarella Gardens
₹17,947 per night
SUPERHOST
  1. Entire cabin
  2. Monterey
Secluded cabin with babbling brook
₹18,204 per night
  1. Entire residential home
  2. Great Barrington
Morgan's Millhouse (Front)
₹9,809 per night