Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

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.

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

Stockbridge, MA 01262

Price$27,000The price has recently decreased

Est. Mortgage: $/month

Rented

Listing Number X39858986

  • Non-MLS Vacation Rentals

RENTED for July and August 2018 $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

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: 3.94% last updated on 2017-12-21

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

$25,000 for 30 days - available July and August.   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: 3.94% last updated on 2017-12-21

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

LOTS OF FUN, RENOVATED COLONIAL IN GREAT BARRINGTON ON 2.7 ACRES. MINUTES TO DOWNTOWN, CLOSE TO EVERYTHING.

Great Barrington, MA 01230

Price$22,000The price has recently decreased

Est. Mortgage: $/month

Listing Number 1230

  • Non-MLS Vacation Rentals
  • LocationType Great Barrington
  • Bathroom 5
  • Bedrooms 5
  • Sleeps 10

Splendid 1800 Colonial Farmhouse on a private, peaceful, flat 2.7 acres just minutes to downtown 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 with fireplace, living room with fireplace, first floor bedroom with a full bath, and a beautiful sun porch that lives up to its name. Encompassing over 3,600 square feet of living space, there is, 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 a wading pool, and a wooden cabana with for entertaining and relaxing. 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. Price upon request.

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: 3.94% last updated on 2017-12-21

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

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: 3.94% last updated on 2017-12-21

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

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: 3.94% last updated on 2017-12-21

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

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: 3.94% last updated on 2017-12-21

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; JULY 2018 RENTED; AUGUST 2018 $14,000 RENTED  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

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: 3.94% last updated on 2017-12-21

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
  • 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: 3.94% last updated on 2017-12-21

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

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

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: 3.94% last updated on 2017-12-21

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

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: 3.94% last updated on 2017-12-21

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

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: 3.94% last updated on 2017-12-21

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

Stockbridge Chalet

Stockbridge, MA 01260

Price$12,000The price has recently decreased

Est. Mortgage: $/month

Listing Number X89533040

  • Non-MLS Vacation Rentals
  • Property Name Stockbridge Chalet

$12,000/ month July & August RENTED; $4,000/ month Winter season; $3,500/ month longer term plus utilities; contact us for pricing in all other seasons 5 Bedroom 3.5 baths Stockbridge Chalet Style house a couple of miles from Tanglewood Main Gate. First floor Master bedroom suite with TV room that can convert into another bedroom. Living room with large fireplace and cathedral ceilings that connects to the kitchen and dining room.     

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: 3.94% last updated on 2017-12-21

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