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Vacation Rentals in Stockbridge

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Early 1800s Greek Revival Farmhouse – Property 124735

  • Stockbridge rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, town, air-conditioning
  • Calendar Last Updated On: Oct 6, 2008
Welcome to our family get-away which we also rent. Set on 2 acres in the Stockbridge hamlet of Glendale, the house is conveniently located - just a short walk to...

Brand New, Beautiful, Four Season Berkshire Cottage by the beach – Property 142178

  • Stockbridge rental - cottage, 3 bedrooms, sleeps 7, 1 bathroom, 1 half bath, beach, lake, air-conditioning
  • $900 - $2,750/week
  • Calendar Last Updated On: Oct 1, 2008
This brand new Beautiful, 3 bedroom, four season cottage with library, sleeping loft, located by Lake Mahkeenac in Stockbridge, Massachusetts.

Charming Lakefront on Stockbridge Bowl for Fall foliage – Property 132791

  • Stockbridge rental - house, 3 bedrooms, sleeps 8, lake, rural, washing machine
  • Calendar Last Updated On: Sep 25, 2008
Book Early For Fall foliage 2008. Come visit our newly furnished home with a spacious 2 story living room and gaze out of the row of glass doors facing the lake.

Spacious studio in garden setting, attractively furnished – Property 125147

  • Stockbridge rental - studio, sleeps 3, 1 bathroom, village, swimming pool
  • Calendar Last Updated On: Sep 15, 2008
Newly renovated spacious studio near Stockbridge town hall and Chime tower. Property overlooks golf course in tranquil garden setting.

OverBrook - Great local Ski conditions! - packed powder & great base – Property 101135

  • Stockbridge rental - house, 3 bedrooms, sleeps 12, 2 bathrooms, 1 half bath, lake, town, air-conditioning
  • Calendar Last Updated On: Sep 15, 2008
Enjoy the scenic views and serenity or explore the local waterways by launching your canoe on the brook running through this 4.8 acre property.

Fabulous Location! Charming 3 story cottage in a unique setting. – Property 136884

  • Stockbridge rental - cottage, 3 bedrooms, sleeps 5, 2 bathrooms, rural, village, swimming pool
  • Calendar Last Updated On: Sep 1, 2008
Charming 3 story cottage in a unique setting. Furnished 3 bedroom. 2 bathroom house with front/back porches, a part of larger estate in Stockbridge, in heart of the...

Historic Colonial by Gardens / Tanglewood – Property 104441

  • Stockbridge rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, air-conditioning, washing machine
  • Calendar Last Updated On: Aug 15, 2008
A 2 acre hilltop location overlooking beautiful Berkshire Mountains and Botanical Gardens, this historical central entrance colonial, built in 1800's, has updated...

Tanglewood favorite-book for labor day or 2009 – Property 190100

  • Stockbridge rental - house, 4 bedrooms, sleeps 7, 3 bathrooms, 1 half bath, downtown, lake, washing machine
  • $2,000/week
  • Calendar Last Updated On: Aug 12, 2008
Charming & spacious 1930s cottage style house surrounded by 3 acres of lawn, trees and perennial beds in the beautiful estate area at the West end of Main Street in...

Fabulous Home with Pool & Hot Tub ~ July and August Special Offer – Property 101829

  • Stockbridge rental - house, 4 bedrooms, sleeps 6, 2 bathrooms, mountain, resort, swimming pool
  • Calendar Last Updated On: Jul 29, 2008
Beautifully furnished, recently renovated Stockbridge home centrally located 3 miles from Tanglewood, 1 mile from Norman Rockwell.

Charming Stockbridge riverside home surrounded by historic hiking trails – Property 187295

  • Stockbridge rental - house, 2 bedrooms, sleeps 6, 1 bathroom, 1 half bath, town, air-conditioning
  • $1,500/week
  • Calendar Last Updated On: Jul 10, 2008
The last house on a quiet street ending at a suspension footbridge crossing the Housatonic river. This turn of the century home is artist owned.

Convenient to Beach, Tanglewood and All Berkshire Amenities – Property 125379

  • Stockbridge rental - cabin, 2 bedrooms, sleeps 6, 1 bathroom, beach, mountain, washing machine
  • $1,500/week
  • Calendar Last Updated On: Jul 1, 2008
Newly renovated cabin in wooded community with wall to wall carpeting, washer and dryer. Walk to town beach. 1.5 miles to Tanglewood.

Stockbridge: Architect's Home, Walk to Tanglewood – Property 124747

  • Stockbridge rental - house, 4 bedrooms, sleeps 11, 2 bathrooms, 1 half bath, lake, mountain, air-conditioning
  • Calendar Last Updated On: Jun 22, 2008
Unique architect's home set in 4 acres private estate, 5 minute walk to Tanglewood. This unique home (lots of wood, glass and stone) offers 4 bedrooms (1 king, 2...

Charming Country Cottage, 1 mile from Tanglewood , very private – Property 124653

  • Stockbridge rental - cottage, 2 bedrooms, sleeps 6, 1 bathroom, mountain, rural, washing machine
  • $900/week
  • Calendar Last Updated On: Jun 2, 2008
Secluded, romantic, woodsy location 1 mile from Tanglewood. 3 miles form Stockbridge and Lenox. Stone fireplace, cathedral ceilings, screened porch.

Ice Glen Rd Stockbridge - Private and Close to All Cultural Attractions & Skiing – Property 176891

  • Stockbridge rental - house, 3 bedrooms, sleeps 8, 4 bathrooms, 1 half bath, mountain, rural, swimming pool
  • $3,750 - $7,000/week
  • Calendar Last Updated On: Apr 14, 2008
Stunning home on best street in Stockbridge. Eighteen secluded acres at end of private road. Adjacent to Beartown State Forest.

Private Large Contemporary Victorian / Tangelwood – Property 145364

  • Stockbridge rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, mountain, rural, air-conditioning
  • $1,700/week
  • Calendar Last Updated On: Apr 7, 2008
6 acre very private hilltop location, overlooking beautiful Berkshire Mountains. The large open living room with fireplace is perfect for entertaining / dinning.

Artist Sanctuary in Stockbridge - Booked thru August 08 – Property 170971

  • Stockbridge rental - apartment, sleeps 3, 1 bathroom, mountain, town, accept credit card
  • Calendar Last Updated On: Mar 13, 2008
This lovely, bright, newly constructed studio apartment is prefect for a writer's /Artist retreat, a couple looking for a weekend getaway or a small family vacation...

Unique Townhouse in the Heart of Stockbridge-6/28 thru 8/31 Special – Property 146723

  • Stockbridge rental - townhome, 3 bedrooms, sleeps 8, 2 bathrooms, lake, town, air-conditioning
  • Calendar Last Updated On: Jan 7, 2008
This charming and unique property located across the street from the Red Lion Inn started life in the nineteenth century as a carriage house but has been in...

The Tanglewood Suites – Property 109031

  • Stockbridge rental - cottage, 2 bedrooms, sleeps 4, 1 bathroom, mountain, air-conditioning
  • Calendar Last Updated On: Dec 17, 2007
The Cottage is located on 2 acres with mountain views one mile from Main Street, Stockbridge; less than 5 minutes from Tanglewood, Norman Rockwell, The Marians, and...

Spectacular Mountain Perch with Views – Property 123523

  • Stockbridge rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, mountain, rural, air-conditioning
  • Calendar Last Updated On: Dec 17, 2007
This modern architect-designed three bedroom/ two bath home (sleeps 6) sits high on a bluff on 22 acres with wonderful southern and western mountain views featuring...

WoodsWhole – Property 216511

  • Stockbridge rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, beach, river, swimming pool
  • Calendar Last Updated On: Dec 17, 2007
This three-bedroom/2.5-bath home is the perfect vacation rental with all the comfort and amenities of an expensive resort. Enjoy 16 acres of total privacy, extensive...
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