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30 Houses

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Retreat in the Woods

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$230

Great rentals within 20 miles that match your search

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$262

Flight's End-A Country Home with Babbling Brook

Hawley house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Perfect getaway” We spent few days there. It is very quiet and private. We loved the retro look. Looking forward going there again. It was New Year's eve we were hoping for.

Price per night from

$217

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$429

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$2,855

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

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Price per night from

$720

OWL'S NEST LODGING

Conway apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$196

Christmas in The Berkshires

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$257

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

Price per night from

$343

Whitman Woods - A Berkshire Vacation

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$172

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$337

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

Price per night from

$260

Marigold Room in Victorian house

Shelburne Falls private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$143

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$566

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$217

Welcome to the Blooming Inn Shelburne Falls, AKA Dancing Bear Guest House Twin

Shelburne Falls private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$98

Balcony Room in Victorian 2 minutes walk to delightful Shelburne Falls center.

Shelburne Falls private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$144

Private Country home near Berkshires

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$98

North Getaway Cottage

Williamstown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$172

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$172

Sadawga Springs Retreat

Whitingham house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$401

1880s Home with a Postcard View

Williamstown house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$195

Charming Affordable Home for groups up to 14

Shelburne Falls house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 14

“Beautiful house in beautiful village!” Thank you for the use of your beautiful house. It was perfect for our wedding weekend. Everyone was very comfortable and had a great time. Looking forward to coming back again in the future.

Price per night from

$573

Berkshire house w/ fireplace, A/C, WiFi & laundry

Plainfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

“Peaceful country home” Beautiful, welcoming home in a perfect location. Warm and inviting living room; bright, airy bedrooms.

Price per night from

$234

The Stephentown Hotel!

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$109

Cute two bedroom

Williamsburg apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$138

6BR Berkshire Bliss - 38 private acres - close to skiing and town

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

Price per night from

$796

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$572

Responds fast! avg. 1 hour 31 minutes

Price per night from

$122

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