Stockbridge Rentals

Updating...

age 0-16
31 Results

Relevance

Price: low to high

Price: high to low

Reviews

31 Houses

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Air conditioning

All filters match

Price per night from

$801

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Air conditioning

All filters match

Price per night from

$458

Great rentals within 20 miles that match your search

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$262

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.

Match: Air conditioning

All filters match

Price per night from

$372

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.

Match: Air conditioning

All filters match

Price per night from

$486

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$429

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 14 minutes

Match: Air conditioning

All filters match

Price per night from

$229

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Match: Air conditioning

All filters match

Price per night from

$721

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

Match: Air conditioning

All filters match

Price per night from

$817

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$152

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Air conditioning

All filters match

Price per night from

$572

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$343

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$196

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.:)))

Match: Air conditioning

All filters match

Price per night from

$171

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Air conditioning

All filters match

Price per night from

$401

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$260

Match: Air conditioning

All filters match

Price per night from

$1,373

Charming, modernized 1810 Farmhouse perfectly located in Hillsdale, NY

Hillsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$343

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$115

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Ghent house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Air conditioning

All filters match

Price per night from

$228

Charming Guest Suite

Old Chatham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Air conditioning

All filters match

Price per night from

$155

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

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$70

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

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$80

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$172

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$126

Modern, Private on 40 Acres New Renovation

Ashley Falls house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Air conditioning

All filters match

Price per night from

$914

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Air conditioning

All filters match

Price per night from

$659

Private Home Overlooking Stevens Lake (31 Night Min)

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$572

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Air conditioning

All filters match

Price per night from

$686

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Air conditioning

All filters match

Price per night from

$744

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Air conditioning

All filters match

Price per night from

$343

×

Also consider