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Vacation Rentals in Pittsfield

See all Vacation Rentals in Pittsfield
Vacation Village in the Berkshires $105
Vacation Village in the Berkshires

Vacation Village in the Berkshires

276 Brodie Mountain Rd, Hancock, MA
     
    3.9
    of 5, from 25 reviews
    3.0 out of 5.0 Stars

    Located near the slopes, this Hancock condo building is within 6 mi (10 km) of Pittsfield State Forest and Mount Greylock State Reservation Visitor Center and close to winter sports such as skiing lessons. Waubeeka Golf Links and New Lebanon Library are also within 12 mi (20 km).

    Holiday Inn Club Vacations Oak n' Spruce Resort $119
    Holiday Inn Club Vacations Oak n' Spruce Resort

    Holiday Inn Club Vacations Oak n' Spruce Resort

    190 Meadow Street, South Lee, MA
       
      3.5 out of 5.0 Stars

      Conveniently located near the ski slopes, this aparthotel in South Lee is within 3 mi (5 km) of Beartown State Forest, Lee Prime Outlets, and Greenock Country Club. Berkshire Theatre Festival and Mission House are also within 3 mi (5 km).

      Jiminy Peak Mountain Resort $115
      Jiminy Peak Mountain Resort

      Jiminy Peak Mountain Resort

      37 Corey Rd, Hancock, MA
         
        3.9
        of 5, from 11 reviews
        3.0 out of 5.0 Stars

        Located in the mountains, this Hancock condo resort offering ski-in/ski-out access is 6.1 mi (9.7 km) from Mount Greylock State Reservation Visitor Center and within 12 mi (20 km) of Waubeeka Golf Links and Colonial Theater. Berkshire Museum and Hancock Shaker Village are also within 16 mi (25 km).

        The Ponds at Foxhollow by Capital Vacations
        The Ponds at Foxhollow by Capital Vacations

        The Ponds at Foxhollow by Capital Vacations

        3 Foxhollow Drive Route 7, Lenox, MA
           
          3.0 out of 5.0 Stars

          Situated in the entertainment district, this condo building is within 3 mi (5 km) of The Mount, Animagic Museum of Animation, and Lee Library. Greenock Country Club and Shakespeare and Company are also within 3 mi (5 km).

          Wyndham Bentley Brook
          Wyndham Bentley Brook

          Wyndham Bentley Brook

          1 Corey Road, Hancock, MA
             
            4.8
            of 5, from 4 reviews
            3.0 out of 5.0 Stars

            Located in the mountains, this ski-in/ski-out condo building in Hancock is within 6 mi (10 km) of Pittsfield State Forest and Mount Greylock State Reservation Visitor Center and close to winter sports such as cross-country skiing and snowmobiling. Waubeeka Golf Links and New Lebanon Library are also within 12 mi (20 km).

            Garfield Guest House in the Office Complex $75
            Garfield Guest House in the Office Complex

            Garfield Guest House in the Office Complex

            Lee, MA
               
              5.0
              of 5, from 1 reviews
              0.0 out of 5.0 Stars

              Situated in Lee, this apartment building is within a 5-minute walk of Animagic Museum of Animation and Lee Library. Greenock Country Club and Lee Prime Outlets are also within 2 mi (3 km).

              Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
              Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

              Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

              Lee, MA
                 
                0.0 out of 5.0 Stars

                Located near the slopes, this Lee apartment building is within a 15-minute walk of Animagic Museum of Animation and Greenock Country Club and close to winter sports such as cross-country skiing and snowmobiling. Lee Library and Lee Prime Outlets are also within 2 mi (3 km).

                The Freckled Hen's Berkshire Nest
                The Freckled Hen's Berkshire Nest

                The Freckled Hen's Berkshire Nest

                Lee, MA
                   
                  0.0 out of 5.0 Stars

                  Situated in Lee, this vacation home is within 3 mi (5 km) of Animagic Museum of Animation, Lee Library, and Lee Prime Outlets. Greenock Country Club and Wood's Pond are also within 3 mi (5 km).

                  Spacious Log Cabin on 11+ Acres of Private Forest Along The Appalachian Trail
                  Spacious Log Cabin on 11+ Acres of Private Forest Along The Appalachian Trail

                  Spacious Log Cabin on 11+ Acres of Private Forest Along The Appalachian Trail

                  Great Barrington, MA
                     
                    0.0 out of 5.0 Stars

                    Situated in the mountains, this historic cabin is 1.4 mi (2.3 km) from Lake Buel and 1.6 mi (2.5 km) from Ski Butternut. Les Trois Emme Winery is 2.4 mi (3.8 km) away.

                    Berkshire Lake House Vacation Rental $569
                    Berkshire Lake House Vacation Rental

                    Berkshire Lake House Vacation Rental

                    Pittsfield, MA
                       
                      0.0 out of 5.0 Stars

                      Located near the slopes, this Pittsfield vacation home is on a lake, 2.7 mi (4.3 km) from Pittsfield State Forest, and within 6 mi (10 km) of Mount Greylock State Reservation Visitor Center and Canoe Meadows Wildlife Sanctuary. Berkshire Athenaeum and Colonial Theater are also within 6 mi (10 km).

                      Beautifully Renovated Lake Buel Cottage $200
                      Beautifully Renovated Lake Buel Cottage

                      Beautifully Renovated Lake Buel Cottage

                      Great Barrington, MA
                         
                        0.0 out of 5.0 Stars

                        Situated near the beach, this vacation home is 0.1 mi (0.1 km) from Lake Buel and within 3 mi (5 km) of Les Trois Emme Winery and Dry Hill. Ski Butternut and Questing are also within 6 mi (10 km).

                        Stunning Private Suite in the Beautiful Berkshires
                        Stunning Private Suite in the Beautiful Berkshires

                        Stunning Private Suite in the Beautiful Berkshires

                        Hancock, MA
                           
                          0.0 out of 5.0 Stars

                          Situated in Hancock, this historic vacation home is within 9 mi (15 km) of Pittsfield State Forest, Mount Greylock State Reservation Visitor Center, and Waubeeka Golf Links. Williams College and Berkshire Athenaeum are also within 12 mi (20 km).

                          Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
                          Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

                          Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

                          Becket, MA
                             
                            0.0 out of 5.0 Stars

                            Located in a rural location, this family-friendly cabin is within 6 mi (10 km) of October Mountain State Forest, Becket Land Trust Historic Quarry, and Jacob's Pillow. Chester Town Hall and Otis Ridge are also within 9 mi (15 km).

                            Two Blocks From the Red Lion Inn & Next to Berkshire Theater
                            Two Blocks From the Red Lion Inn & Next to Berkshire Theater

                            Two Blocks From the Red Lion Inn & Next to Berkshire Theater

                            Stockbridge, MA
                               
                              0.0 out of 5.0 Stars

                              Situated in Stockbridge, this vacation home is within a 15-minute walk of Berkshire Theatre Festival and Mission House. Naumkeag and National Shrine of the Divine Mercy are also within 1 mi (2 km).

                              Your Retro Retreat! Great Location Near Many Berkshire Attractions! Free Wifi!
                              Your Retro Retreat! Great Location Near Many Berkshire Attractions! Free Wifi!

                              Your Retro Retreat! Great Location Near Many Berkshire Attractions! Free Wifi!

                              Adams, MA
                                 
                                0.0 out of 5.0 Stars

                                Situated in Adams, this vacation home is 1.1 mi (1.8 km) from Topia Arts Center and within 3 mi (5 km) of East Hoosac Quaker Meetinghouse and Susan B. Anthony Birthplace Museum. Mass MoCA and Savoy Mountain State Forest are also within 9 mi (15 km).

                                Tentrr - Running Spring Farm
                                Tentrr - Running Spring Farm

                                Tentrr - Running Spring Farm

                                25 Jerusalem Road, Lee, MA
                                   
                                  2.5 out of 5.0 Stars

                                  Situated in Lee, this apartment building is within 3 mi (5 km) of Beartown State Forest, Tyringham Cobble, and Goose Pond Reservation. Ashintully Gardens is 3.1 mi (5 km) away.

                                  Chic Victorian Apt 5 Min From Williams College $110
                                  Chic Victorian Apt 5 Min From Williams College

                                  Chic Victorian Apt 5 Min From Williams College

                                  Williamstown, MA
                                     
                                    0.0 out of 5.0 Stars

                                    Located near the slopes, this Williamstown vacation home is within 1 mi (2 km) of Hopkins Observatory and Williams College and close to winter sports such as sledding. Williams College Museum of Art and Chapin Library of Rare Books and Manuscripts are also within 1 mi (2 km).

                                    Premium Property & Amenities. Ski Season is Filling up Quickly, Don't Miss Out!
                                    Premium Property & Amenities. Ski Season is Filling up Quickly, Don't Miss Out!

                                    Premium Property & Amenities. Ski Season is Filling up Quickly, Don't Miss Out!

                                    Hancock, MA
                                       
                                      0.0 out of 5.0 Stars

                                      Set amidst the mountains, this ski-in/ski-out condo building in Hancock is within 9 mi (15 km) of Pittsfield State Forest and Mount Greylock State Reservation Visitor Center and close to winter sports such as cross-country skiing and sledding. Waubeeka Golf Links and Mount Lebanon Shaker Village are also within 12 mi (20 km).

                                      Collective Hudson Valley
                                      Collective Hudson Valley

                                      Collective Hudson Valley

                                      129 Ostrander Rd., Ghent, NY
                                         
                                        2.0 out of 5.0 Stars

                                        Situated in Ghent, this campground is within 9 mi (15 km) of Omi International Arts Center, Art Omi International Arts Center - Fields Sculpture Park, and Claverack Library. FASNY Museum of Firefighting and Hudson Area Library are also within 9 mi (15 km).

                                        New Listing! Berkshires Jiminy Peak Mountainside Condo
                                        New Listing! Berkshires Jiminy Peak Mountainside Condo

                                        New Listing! Berkshires Jiminy Peak Mountainside Condo

                                        Hancock, MA
                                           
                                          0.0 out of 5.0 Stars

                                          Situated in the mountains, this condo building is 4.6 mi (7.3 km) from Pittsfield State Forest and within 12 mi (20 km) of Mount Greylock State Reservation Visitor Center and Waubeeka Golf Links. New Lebanon Library and Mount Lebanon Shaker Village are also within 12 mi (20 km).

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                                          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.