Vacation Homes in the Berkshires

Search through current vacation homes for sale in the Berkshire County area. Find a variety of listings in towns such as Lenox, Stockbridge, Lee, & many more! The real estate professionals at McLean realtors can help you find the right home for you!

To save your favorite listings and receive email updates when similar properties are post, create an account with us. Sign in here if you already have an account. Please feel free to contact us for more information and to schedule a tour for any real estate below.

2 Woods, Lenox, MA 01240

Price$629,000

Est. Mortgage: $/month

MLS Number 224442

  • Listings Condominium
  • Address 2 Woods Ln # 2
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 3017

Outstanding views over the golf course to the enchanting Berkshire Hills beyond. This upgraded and beautifully decorated town house is not to be missed. Private guest suites, custom built-in office, first luxury master, sunny patio and deck, in a walk to everything location at Cranwell Resort. Can be sold fully furnished, price TBD. How easy is that for a vacation or primary choice in the heart of Lenox! Updated high end dishwasher and fridge, beautiful custom chair rails and moldings throughout home..

Listed by Paula McLean of McLean Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

7 Evergreen, Lenox, MA 01240

Price$439,000

Est. Mortgage: $/month

MLS Number 223262

  • Listings Condominium
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 1800
  • Year Built 2014

Beautiful light, bright and spacious condo with master ensuite on first floor, two other guest bedrooms plus one unfinished bonus room as 4th. bedrm, excerise room, or office. High ceilings, cac, gas fpl., w/d, enclosed porch off living room. Attached garage.Custom window treatments thru-out. Near dining, theater, medical, airports, excellent schools, 2+ Hrs. NYC and Boston, 5 mins. to Tanglewood, Kripalu, walking/hiking trails access from within complex. Everything you could want for vacation or year round comfort. Mint condition!

Listed by Reciprocal Listing: See Realtor Remarks of NON-MEMBER

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

14 Amy, Pittsfield, MA 01201

Price$415,000

Est. Mortgage: $/month

MLS Number 219537

  • Listings Residential
  • Address 14 Amy Ct
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3561

Truly wonderful lifestyle! Exceptional interior finish and quality. Ideal for vacation or primary residence. Exciting new open floor plan with gorgeous decor, colors and finishes. New construction and an amazing value. Three fully finished levels, screen porch, gas fireplace and energy efficiency. Dynamic kitchen.

Listed by Paula McLean of McLean Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

14 Amy, Pittsfield, MA 01201

Price$415,000

Est. Mortgage: $/month

MLS Number 219538

  • Listings Condominium
  • Address 14 Amy Ct
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 3561

Truly wonderful lifestyle! Exceptional interior finish and quality. Ideal for vacation or primary residence. Exciting new open floor plan with gorgeous decor, colors and finishes. New construction and an amazing value. Three fully finished levels, screen porch, gas fireplace and energy efficiency. Dynamic kitchen.

Listed by Paula McLean of McLean Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

16 Evergreen, Lenox, MA 01240

Price$399,000

Est. Mortgage: $/month

MLS Number 222407

  • Listings Condominium
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 1931
  • Year Built 2011

This open design at Lenox Woods is sure to please. Spacious and immaculate with upgraded Kraftmaid cabinetry, Carrera marble, granite and stainless appliances. Enjoy the trials of Kennedy Park Preserve and its 2000 scenic acres right out your door. Hiking, snowshoeing, lush nature and groomed trails enhance this neighboring sanctuary. The ideal location just minutes from, shopping, restaurants, Tanglewood and Lenox Township. Retreat to the upstairs en-suite bedrooms or cozy den. A perfect choice for vacation use or primary ease. The chores of the seasons and exterior care is all done by the HOA, creating a lifestyle of ease. Come see!

Listed by Paula McLean of McLean Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

930 Main, Lanesboro, MA 01237

Price$399,000

Est. Mortgage: $/month

MLS Number 224553

  • Listings Residential
  • Address 930 North Main St
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3047

Imagine relaxing surrounded by nature, the birds are chirping, crickets beeping, water trickling, as you take in the crisp fresh country air. This home offers stunning architecture in a romantic serene setting, with mature landscaping and spectacular views. Make this one your forever home OR your home away from home. Truly spectacular natural light, warm and inviting and creative floor plan. Home offers in-law quarters that has been used as a Vacation mini get away in the past, (home currently zoned as a two family, but when originally built it was a single family home with 6 bedrooms.) Close to Jiminy Peak, MassMoCa, Williamstown Theater, Tanglewood and other Berkshire county attractions.

Listed by Nadine Hiser of KEY REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

930 Main, Lanesboro, MA 01237

Price$399,000

Est. Mortgage: $/month

MLS Number 224545

  • Listings MultiFamily
  • Address 930 North Main St
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 3047

Broker OPEN HOUSE & Networking Event. Tuesday 2:30-4:30pm. Imagine relaxing surrounded by nature, the birds are chirping, crickets beeping, water trickling, as you take in the crisp fresh country air. This home offers stunning architecture in a romantic serene setting, with mature landscaping and spectacular views. Make this one your forever home OR your home away from home. Truly spectacular natural light, warm and inviting and creative floor plan. Home offers in-law quarters that has been used as a Vacation mini get away in the past, (home currently zoned as a two family, but when originally built it was a single family home with 6 bedrooms.) Close to Jiminy Peak, MassMoCa, Williamstown Theater, Tanglewood and other Berkshire county attractions.

Listed by Nadine Hiser and The Dream Team of KEY REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

22 Amy, Pittsfield, MA 01201

Price$385,000

Est. Mortgage: $/month

MLS Number 222230

  • Listings Condominium
  • Address 22 Amy Ct
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2624

Looking for one level living with private guest areas? Then this is ideal. Just the right size for primary or vacation living. Beautiful interior finishes and quality that can't be compared to at this price point. Open floor plan, screen porch, energy efficient gas heat and central A/C. Minutes to town and culture. A perfect choice for many lifestyles.

Listed by Paula McLean of McLean Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

22 Amy, Pittsfield, MA 01201

Price$385,000

Est. Mortgage: $/month

MLS Number 222229

  • Listings Residential
  • Address 22 Amy Ct
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2624

Looking for one level living with private guest areas? Then this is ideal. Just the right size for primary or vacation living. Beautiful interior finishes and quality that can't be compared to at this price point. Open floor plan, screen porch, energy efficient gas heat and central A/C. Minutes to town and culture. A perfect choice for many lifestyles.

Listed by Paula McLean of McLean Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

1136 Barker, Pittsfield, MA 01201

Price$359,000

Est. Mortgage: $/month

Pending

MLS Number 224836

  • Listings Condominium
  • Address 1136 Barker Rd # 25
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2044

Located directly across from the 1800 feet of Richmond Pond shore, this immaculate unit affords water views from the upstairs bedrooms. Inspired by Shaker design, South Pond Farm is truly unique in it's simple yet enchanting architecture and timeless appeal. Hardwood floors, an inviting wood burning fireplace, a cozy first floor den/office, expansive wrap around deck, a private morning courtyard and significant improvements to mechanical systems and interior amenities make this a perfect choice for both year round or vacation living. Enjoy quiet boating, fishing and swimming from the private waterfront, engage in a tennis match or simply lounge at the heated pool of South Pond Farm. This highly desirable and picturesque community is the Berkshire's best kept secret. Allow us to

Listed by Paula McLean of McLean Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 8, 2018
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details