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Berkshire Rentals

If you are looking for a seasonal rental for the ski season or a long-term rental home, Berkshire Property Agents can help you find townhomes, condos, homes with acreage for rent in the Southern Berkshires.

Browse current rentals in the Berkshires. Don't hesitate to contact us with any of your questions.

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STOCKBRIDGE COMPOUND ON PROSPECT HILL ROAD

Stockbridge, MA 01262

Price$27,000The price has recently decreased

Est. Mortgage: $/month

Listing Number X39858986

  • Non-MLS Vacation Rentals

July and August 2019 $27,000/ month - available off Season $12,000/ month - Exquisitely renovated late 1700 antique home with perfect proportions & amazing grounds. High ceilings, multiple fireplaces & historic details, flooded with light. Beautifully sited on over 9 acres on one of the most prestigious roads in the county. Barn, apple orchard, specimen trees, masterful stonework. Secluded and private heated Gunite pool w/ classic pool house, outdoor shower & adventurous boardwalk. 5 Bedrooms and 5 Baths.

Listing courtesy of Christian Deckert of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

PROSPECT HILL RD. IN STOCKBRIDGE

Stockbridge, MA

Price$25,000The price has recently decreased

Est. Mortgage: $/month

Listing Number X28417904

  • Non-MLS Vacation Rentals
  • Bathroom 5
  • Square Feet 4,320
  • Bedrooms 7

$1000/ night 3 night minimum - $25,000/ month July & August; Thanksgiving Nov 18 to 25 $5,000; Christmas & NYE Dec 22 to Jan 5 $5,000/ week.    Located on nearly two level acres on the most picturesque road in Stockbridge, this spectacular residence offers classic style and modern luxury. Designed for entertaining, the first-floor layout has wonderful flow: The living room has a stunning gas fireplace and the dining room opens onto a sparkling kitchen with marble countertops, custom cabinetry,  a Viking range and a pair of stainless-steel beverage refrigerators. The first floor also has a bright den with a wood-burning fireplace, a glamorous powder room, and an enormous screened-in porch with a built-in chef's grill so you can barbecue even on rainy days. The second floor features a master suite with a wood-burning fireplace, sumptuous bathroom, and a sitting room/office as well as another en suite bedroom. On the third floor, there are two more bedrooms with dormer windows and a shared bath.  There is additional entertaining space above the three-car garage: A media room with wet bar overlooks the 36x18 pool as do two guest bedrooms and a full bath. Thoughtfully renovated with central air-conditiioning and radiant heat, this refined home is ideally situated just minutes from Tanglewood, the Stockbridge Bowl and the Red Lion Inn. No Pets!

Listing courtesy of Christian Deckert of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

BOULDERWOOD

185 BEARTOWN MOUNTAIN Rd, Monterey, MA

Price$25,000The price has recently decreased

Est. Mortgage: $/month

Listing Number Boulderwood

  • Non-MLS Vacation Rentals
  • Property Name BOULDERWOOD

Casually elegant and beautiful shingled eco-luxury mountaintop home with rare and extraordinary protected southerly long-range views, abutting 12000 acre Beartown State Forest. Carefully and exquisitely crafted, the gracious rooms feature four fireplaces with a hefty stone central core, mahogany windows and doors, and radiant heated wood floors. The horse barn has three generous stalls, a tack room, and caretaker's quarters. Horses enjoy organic pastures and an outdoor arena that could easily be a tennis court. The private setting and views are unmatched in the southern Berkshires, and the quality of construction speaks for itself. $17,500 for June. $25,000 for July and August, each. 

Listing courtesy of Tim Lovett of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

WILLARD HILL

Stockbridge, MA

Price$17,000The price has recently decreased

Est. Mortgage: $/month

Listing Number X85079763

  • Non-MLS Vacation Rentals
  • Date Available 05/24/2018
  • Bathroom 4
  • Property Name WILLARD HILL
  • Bedrooms 7

$17,000/month July and August Classic, beautifully renovated 1833 family home in perfect location. Sumptuous living spaces.  Fun cooks’ kitchen.  Six + bedrooms and 4 bathrooms. Three glorious porches for reading, lounging and dining. Two back porches overlook the Larrywaug Brook with swimming hole and lots of summer fun for family. The third floor includes a fabulous yoga/dance space. Beautiful perennial gardens, fruit trees and vegetable gardens. Gracious and comfortable throughout!    

Listing courtesy of Claudia Crane of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

GREEK REVIVAL IN GREAT BARRINGTON

Great Barrington, MA 01230

Price$16,000The price has recently decreased

Est. Mortgage: $/month

Listing Number X85184892

  • Non-MLS Vacation Rentals
  • Bathroom 3
  • Square Feet 3,700
  • Bedrooms 5

$16,000/ski season; January - March 15 (inquire about monthly rentals) Greek Revival with two working fireplaces, hot tub, outdoor spaces for coffee and cocktails, five comfortable bedrooms and central air. Located on "the hill" and just a short stroll to Great Barrington's theater, movies and restaurants...or a bike ride to the local beach...minutes to Butternut and Catamount. The house has been updated for the discerning vacationer with no expense spared. Fresh paint, newly furnished, floors refinished, master bath and kitchen renovated and wi-fi throughout. Three blocks to downtown CONTACT ANNIE AT OKERLANG@YAHOO.COM  

Listing courtesy of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Great Barrington Carriage house

Great Barrington, MA 01230

Price$15,000The price has recently decreased

Est. Mortgage: $/month

Listing Number X41941738

  • Non-MLS Vacation Rentals
  • Sleeps 6

$15,000/ July; $15,000/ August - South facing in town Carriage Barn tucked away for privacy. Open kitchen, dining and livingroom with fireplace. First floor master bedroom and bath. Screened porch. Upstairs are two more guest bedrooms that share a full bath. Bay windows, beautiful wood floors, custom cabinetry & high end finishes throughout. Central A/C and high speed internet. No pets.

Listing courtesy of Christian Deckert of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Lenox Cape in Schermerhorn Park

Lenox, MA 01240

Price$14,000The price has recently decreased

Est. Mortgage: $/month

Listing Number X34430542

  • Non-MLS Vacation Rentals
  • Date Available 08/01/2016
  • Bathroom 2
  • Square Feet 1,632
  • Bedrooms 3

$5,000/ month; $3,500/ week; AUGUST 18 to 31 2018 available - Modern, bright and renovated. Mid Century vogue furnishings hardwood floors and central A/C are just some features you will find. This lovely 3 Bedroom home is located on a quiet dead end street and walking distance into downtown Lenox. The Tanglewood Main gate is less than a mile away. Across the street from the house enjoy deeded access to miles of hiking trails through Canyon Ranch and Schermerhorn Park. Enjoy all that Lenox has to offer in this pristine location. High speed internet with WiFi. Broker owned.    

Listing courtesy of Christian Deckert of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

TYRINGHAM, MA

TYRINGHAM, MA 01264

Price$13,500The price has recently decreased

Est. Mortgage: $/month

Listing Number X40786802

  • Non-MLS Vacation Rentals
  • LocationType Tyringham, MA
  • Winter Rental
  • min rental period winter 1 month
  • Bathroom 3

$13,500 July, $13,500 August. Exquisitely renovated and tastefully appointed farmhouse getaway set high in the picturesque Tyringham Valley. 10 minutes to either Stockbridge or Lee. Located on one of the loveliest roads in the county with gorgeous southeasterly views. Stroll down the lane to the private spring-fed swimming pond or tennis court or wander down the hill and hike the Tyringham Cobble. A perfect place to spend a picturesque holiday and ski season (15 minutes to Butternut Ski.) Close to essential Berkshire attractions: Tanglewood, Jacob's Pillow, etc. Also available for year-round, long-term rental at a reduced cost. Please contact agent. Filled with light, the first floor features an open kitchen, dining room, bathroom with shower, living room with delightful seating areas, a quiet office space as well a second, beamed living room and tv / movie area as well as a screened porch perfect for summer dinners. On the second floor, two full bedrooms and a full bath as well as twin bedroom and a smaller bedroom with bunk beds comprise one section while the master bedroom and a second full bath are privately situated at the western end. Weekly housekeeping included as well as all utilities. Housekeeping and utilities for year-round or long-term rental are excluded. Renown for its quiet beauty and spectacular views, the Appalachian Trail crosses the Tyringham Valley and two Trustees of Reservations properties - Ashintully and the Cobble offer unparalleled hikes.  

Listing courtesy of Selina Lamb of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

FARMHOUSE PERFECTION - SUMMER IN THE BERKSHIRES

Sheffield, MA

Price$12,500The price has recently decreased

Est. Mortgage: $/month

Listing Number X81061940

  • Non-MLS Vacation Rentals
  • Date Available 06/29/2018
  • LocationType SHEFFIELD

This rambling farmhouse is the perfect country retreat. It is located down a quiet dirt road and situated at the foothills of the Berkshire mountains. Built in 1990 by a well known architect, it was recently updated and is the home of an interior designer. Tucked away on 16 acres, this home has 5 bedrooms and 2.5 baths. Enjoy your morning coffee outside in the landscaped courtyard, screened porch, garden, or stone patio that overlooks the mountains. Beautiful large natural fire pit area. The kitchen is open and filled with light from a wall of windows. A cozy family room and living/game room each have a fireplace and French doors leading to the outside patios. There is a charming first floor bedroom which is accessed thru a library. The upstairs has 4 bedrooms off of a wide, window lined hallway. The master has a walk in closet, peaked ceiling and full bathroom. The second bedroom has a fireplace and bay window. The third bedroom has a beautiful built in headboard. The fourth bedroom is set at the end of the hallway and could be used as a second master bedroom. Each room has been decorated using texture and materials to create a truly special home.  All bedrooms and the living room have window air conditioners. There is also a partially finished basement that can be used as a playroom, studio, exercise room, etc. This home is private yet close to amazing food, shopping, and cultural events. Salisbury, Ct and Great Barrington are a 10 minute drive. Tanglewood, Shakespeare and Company, Jacobs Pillow, Farmers Markets, Theaters, hiking trails, lakes and museums are all close by. This is a very special home. 1 month rental minimum July: $12,500/month August: $12,500/month

Listing courtesy of Claudia Crane of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Egremont Contemporary with Views

Egremont, MA 01258

Price$12,500The price has recently decreased

Est. Mortgage: $/month

Rented

Listing Number X28101252

  • Non-MLS Vacation Rentals
  • Maximum Occupants 10
  • Sleeps 10

$12,500/JULY & AUGUST  Cool contemporary privately located in Egremont with 3 bedrooms and 2.5 baths and southwestern views. Located down a long driveway on top of the hill. The main floor has a large master suite with walk-in closet, bath with soaking tub and shower. The first-floor guest bedroom has its own private bath. Open living, dining and kitchen area with fireplace. The den has a pull out sofa and could easily be turned into a fourth bedroom. Upstairs has a huge loft space with TV and a bedroom.

Listing courtesy of Christian Deckert of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

WHITE PINES CONDOMINIUM

Stockbridge, MA 01262

Price$12,000The price has recently decreased

Est. Mortgage: $/month

Listing Number WHITEPINE

  • Non-MLS Vacation Rentals

Light, bright and spacious white pines condo- two level contemporary living, first floor open p-lan- large first floor master suite- living/dining room, eat in kitchen, half bath skylights, interior balcony, fireplace, vaulted ceiling, sw facing deck. - sunny walkout lower level with a bedroom, den, bathroom and a oversized bonus room with windows and closets  pastoral and seasonal mountain views, attached garage, private beach at the stockbridge bowl kayak space, indoor pool, 2 tennis courts, gym, pets allowed, walking distance to tanglewood, wheatleigh, close to lenox- 2.5+ hours from boston or nyc

Listing courtesy of Barbara Schulman of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Modern & Cool 3 - 4 Bedroom Loft in Sheffield

Sheffield, MA

Price$12,000The price has recently decreased

Est. Mortgage: $/month

Listing Number X66091631

  • Non-MLS Vacation Rentals

Available 2019 June $10,000; $12,000/ July; $12,000/ August - Surrounded by fields and on top of the textile studio is this sleek Loft Style space with a large open kitchen, dining and fantastic in and outdoor living area. Comfy TV/ lounge area. Beautiful chefs kitchen with stone work spaces and high end appliances. Screened porch with BBQ, sun deck & central A/C. The master bedroom and bath is on the main floor together with a second bedroom that has its own bath. Bonus room that could serve as a third bedroom. There is one more bedroom upstairs. 

Listing courtesy of Christian Deckert of Berkshire Property Agents

Berkshire Property Agents
12 Railroad Street
Great Barrington MA, 01230
Office: 413-528-6800

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Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.9% last updated on 2018-10-11

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.