Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

Berkshire Rentals

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

Search Simpler: Register now to save your favorite listings and custom searches. Best of all, we'll email you when new properties that match your criteria hit the market.

STOCKBRIDGE COMPOUND ON PROSPECT HILL ROAD

Prospect Hill Rd., Stockbridge, MA 01262

Rental Price$27,000The price has recently decreased

InternalID X39858986

  • Non-MLS Vacation Rentals

Available for July 2017 $27,000 - 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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

Prospect Hill Rd., Stockbridge, MA

Rental Price$25,000The price has recently decreased

InternalID X28417904

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

$25,000/ AUGUST; JULY RENTED   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 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 fromTanglewood, 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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

ROSE HILL CONTEMPORARY

Rose Hill Dr., Alford, MA

Rental Price$20,000The price has recently decreased

InternalID X77373656

  • Non-MLS Vacation Rentals
  • Location Alford
  • Bathroom 3
  • Square Feet 3,059
  • Bedrooms 5

$5,000/ WEEK, $20,000/ JULY, $20,000/ AUGUST, $10,000/ MONTH LONG TERM, AVAILABLE STARTING IN JULY 2017. JUST TEN MINUTES FROM TWO SKI MOUNTAINS - BUTTERNUT AND CATAMOUNT - THIS BEAUTIFULLY RENOVATED HOME IS A LUXURIOUS PLACE TO UNWIND AFTER A DAY ON THE SLOPES.   With spectacular views from every room and rustic charm, it’s also a cheerful house to spend winter days. The kitchen with imported Belgium blue stones has zinc and marble counters, stainless appliances and is open to the living room with antique fireplace and southern views. A grand first-floor master bedroom wing with windows on 3 sides has a big tub and a two-person shower. The great room on the other side of the house has radiant floors and can be used for dining, watching TV, playing piano or board games. Upstairs, there are two more spacious bedrooms (each with a window seat) that share a full bath. A big mudroom not only provides storage for winter sports gear but also acts as a buffer to keep cold and snow outside. The private rural location is conveniently located just five minutes to the shops, restaurants and theaters of downtown Great Barrington.  

Listing courtesy of Christian Deckert of Berkshire Property Agents

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

UPDATED COLONIAL IN GREAT BARRINGTON ON 2.7 ACRES. MINUTES TO DOWNTOWN, CLOSE TO EVERYTHING.

43 West Sheffield Road, Great Barrington, MA 01230

Rental Price$19,000The price has recently decreased

InternalID 1230

  • Non-MLS Vacation Rentals
  • Bathroom 5
  • Bedrooms 5
  • Sleeps 10

Gorgeous 1800 country Colonial on a private, peaceful 2.7 acres just minutes to main street Great Barrington. Restored and graciously expanded, the home features top-of-the-line everything and fabulous interior decoration. There is an eat-in kitchen, dining area, living room with fireplace and a beautiful sun porch that lives up to its name. Encompassing over 3,600 square feet of living space, there is a ground floor master ensuite, second-floor master suite also with private bathroom, and three additional bedrooms and two-and-a-half bathrooms for lots of sleeping space for family and friends. The flat, pastoral yard has ample outdoor entertaining space including a huge patio with reflecting pool and abutting covered cabana. The property is located within walking distance to Wyantenuck Country Club for swimming and golfing, is less than 15 minutes to Tanglewood and a half an hour drive to Hudson’s Amtrak Station. The perfect country retreat and vacation.

Listing courtesy of Barbara Schulman of Berkshire Property Agents

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

Rental Price$16,000The price has recently decreased

InternalID 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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

, Lee, MA

Rental Price$15,000The price has recently decreased

InternalID X44387022

  • Non-MLS Vacation Rentals
  • Bathroom 5
  • Bedrooms 5
  • Sleeps 12

$15,000/AUGUST  $4500/mo plus utilities for one year.   1850'S GREEK REVIVAL is in the perfect location between Stockbridge and Lenox. This historic home has 21st Century comfort and style, both rambling and intimate.  Two floors of masterfully finished living space with 5 1/2 sumptuous baths, multiple master suites, informal living room with fireplace upstairs and alternative gathering space with fireplace on the main floor offer separate and generous guest quarters and rooms up and down for family and friends. The rustic-chic dining room has a large hearth and a spacious, bright, eat-in cook's kitchen with exquisite features leading to a screened porch. The home is 4,614 square feet of comfort and charm set back off the road on seven acres with a golf course just up the street and all things "Berkshires" within easy access . 

Listing courtesy of Deborah Levinson of Berkshire Property Agents

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

Great Barrington Carriage house

Silver Street, Great Barrington, MA 01230

Rental Price$15,000The price has recently decreased

InternalID 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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

French Country House

Hurlburt Road, Great Barrington, MA 01230

Rental Price$13,500The price has recently decreased

InternalID X14408614

  • Non-MLS Vacation Rentals
  • Property Name French Country House

$10,000/JUNE, $13,500/JULY & August  French Country house with 4 bedrooms, pool and tennis court. Formal entry from the circular driveway, with marble flooring, a large Den, powder room and renovated Living room. Lots of glass in the kitchen, formal dining room and guest wing. Upstairs is the Master bedroom suite and 2 more guest bedrooms that share a bath. Also available for long term rental at $4,000/ month plus utilities.

Listing courtesy of Christian Deckert of Berkshire Property Agents

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

TYRINGHAM, MA

Jerusalem Road, TYRINGHAM, MA 01264

Rental Price$13,500The price has recently decreased

InternalID X40786802

  • Non-MLS Vacation Rentals
  • Location Tyringham, MA
  • Bathroom 3
  • Property Name TYRINGHAM, MA
  • Maximum Occupants 9

$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. Available as a new rental for the first time in ten years. 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. 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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

Egremont Contemporary with Views

Mallard Rd, Egremont, MA 01258

Rental Price$12,500The price has recently decreased

InternalID 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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

1834 GREEK REVIVAL & CARRIAGE BARN ON FOUR ACRES IN HISTORIC SECTION OF STOCKBRIDGE

4 Willard Hill, Stockbridge, MA 01262

Rental Price$12,000The price has recently decreased

InternalID X42945421

  • Non-MLS Vacation Rentals
  • Bathroom 5
  • Square Feet 3,100
  • Bedrooms 4

1834 Brick Greek revival on historic Willard Hill Road, regally sited on four lovely acres, wit19th-centurytury red carriage barn. Recently renovated, including the newer kitchen, master suite with a dressing room and marble bath, and an artist’s studio or home office. French doors in the dining room open to the sylvan backyard, and the stone terrace by the Japanese maple has full sun all day. Minutes from Tanglewood and Stockbridge Bowl. 

Listing courtesy of Tim Lovett of Berkshire Property Agents

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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

Boardman Street, Sheffield, MA

Rental Price$12,000The price has recently decreased

InternalID X66091631

  • Non-MLS Vacation Rentals

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

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 4.15% last updated on 2017-02-16

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