Sheffield Rentals

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52 Houses

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$686

Great rentals within 20 miles that match your search

Iris Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$172

Horse Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$172

Garfield House

Lee apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$201

Newly Renovated Lakefront Getaway on Robinson Pond

Copake house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$287

The Cottage at Great Falls

Falls Village cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Perfect getaway location with all the amenities” Perfect getaway location with all the amenities – including a fireplace for a perfect winter stay. The cottage was clean and inviting, and the character of the furnishings and layout were incredible. Whether you want to stay in or venture out to nearby stores and restaurants, the cottage really is a perfect location for a vacation escape.

Price per night from

$275

Berkshire Farmhouse Vacation

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

Price per night from

$298

Escape to the Berkshires!

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 24 minutes

Price per night from

$315

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$859

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$172

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 14 minutes

Price per night from

$229

Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$206

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, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.

Price per night from

$229

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$859

Fabulous Post & Beam Berkshire Rental

Monterey house

  • 2 bathrooms
  • sleeps 7

Price per night from

$205

Total Privacy! Tanglewood Retreat With Berkshire Views!

Hillsdale house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

Price per night from

$1,145

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

Price per night from

$818

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$153

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$327

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$196

Babbling Brook Retreat

Lakeville apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$264

The FarmHouse

Millerton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$287

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$573

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$344

Lake House

Lakeville house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Responds fast! avg. 2 hours 6 minutes

Price per night from

$687

The Barn at Copake Lake

Craryville barn

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 14

Price per night from

$686

Twin Island Lake House

Pine Plains house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$411

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$401

CHALET-STYLE STUNNER ON A COUNTRY ROAD

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$281

Kellogg Haus

Falls Village house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$458

Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY

Hillsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$344

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$115

Holiday Inn Club Vacations Oak N' Spruce 2br suite Friday check-ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$81

Holiday Inn Club Vacations Oak N' Spruce 2BR Suite SATURDAY Check-Ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$70

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

Price per night from

$373

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!

Price per night from

$274

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))

Price per night from

$171

Hillhouse Log Cabin

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

Price per night from

$487

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