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The Berkshires Vacation Packages

This mountain range in west Massachusetts combines spectacular nature, world-class cultural destinations and charming New England towns. 

The Berkshires is a picturesque mountain range that runs for 98 miles (158 kilometers) along Massachusetts west border. Known for its scenic beauty and its cultural offerings, the Berkshires is one of the state’s top vacation destinations.

Bring a pair of comfortable hiking boots and explore the beautiful wilderness. Hike some of the famous Appalachian Trail, which runs through the Berkshires on its 2,160-mile (3,476.18-kilometer) journey. The Berkshires portion of the trail passes through spectacular peaks such as Mount Greylock and Mount Everett, along with small New England towns.

Explore the trees at the “living tree library” of Hebert Arboretum. This 231-acre (93.5-hectare) park lies in the city of Pittsfield, the largest town in the Berkshires. The arboretum is home to fields, forests and wildflowers. During the spring and fall, the garden is host to migrating songbirds.

Surround yourself with flowers at the Berkshire Botanical Garden in Stockbridge, 14 miles (22.5 kilometers) south of Pittsfield. Browse more than 3,000 species of plants in the botanical garden, which is one of the oldest public gardens in the United States. It was founded in 1934. Stay in Stockbridge to visit the Norman Rockwell Museum of Art, which has the world’s largest collection of work by the famous American artist. Rockwell spent the last several decades of his life in the town, and the museum displays over 500 pieces of his art. 

If you’re in Stockbridge in summer, visit Tanglewood. The music venue is the summer home of the Boston Symphony Orchestra and hosts regular music concerts.

Drive 1-hour north of Stockbridge to North Adams for the Massachusetts Museum of Contemporary Art, one of the largest and most renowned contemporary art centers in the United States. Look through 19 galleries in the converted factory space. 

The best time to visit the Berkshires is in summer, when the Boston Symphony Orchestra is in residence and many visitors flock to the mountains from New York and Boston. Cold winters are best enjoyed indoors, but there are plenty of museums, concert halls and theaters to keep visitors occupied. 

To learn more about all there is to do in the region, visit the official Berkshires of Western Massachusetts tourism website.


Top Hotel Deals

See all 308 Properties in The Berkshires
Days Inn by Wyndham Great Barrington ¥8,217
Reviewed on Jun 12, 2019
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Days Inn by Wyndham Great Barrington

Days Inn by Wyndham Great Barrington

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
     
    3.8 of 5
    2.0 out of 5.0 Stars

    Beautiful setting,near town, big room very clean!!!!!

    The Red Lion Inn ¥11,889
    Reviewed on Jun 14, 2019
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    The Red Lion Inn

    The Red Lion Inn

    30 Main Street, Stockbridge, MA
       
      4.4 of 5
      3.5 out of 5.0 Stars

      The Red Lion Inn is a wonderful historic property with great country charm.

      Yankee Inn ¥10,644
      Reviewed on Jun 12, 2019
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      Yankee Inn

      Yankee Inn

      461 Pittsfield Rd, Lenox, MA
         
        4.0 of 5
        2.5 out of 5.0 Stars

        staff was really friendly and helpful. Didn't care for the coffee. Breakfast was good.

        Howard Johnson by Wyndham Lenox ¥7,378
        Reviewed on Jun 3, 2019
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        Howard Johnson by Wyndham Lenox

        Howard Johnson by Wyndham Lenox

        462 Pittsfield Rd, Routes 7 and 20, Lenox, MA
           
          3.6 of 5
          2.0 out of 5.0 Stars

          Friendly, helpful staff. Nice family staffed facility.

          Hampton Inn & Suites Berkshires Lenox ¥15,103
          Reviewed on Jun 4, 2019
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          Hampton Inn & Suites Berkshires Lenox

          Hampton Inn & Suites Berkshires Lenox

          445 Pittsfield Rd, Lenox, MA
             
            4.6 of 5
            2.5 out of 5.0 Stars

            Very clean, no hassle, free WiFI and decent free breakfast

            Seven Hills Inn ¥11,620
            Reviewed on May 26, 2019
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            Seven Hills Inn

            Seven Hills Inn

            40 Plunkett Street, Lenox, MA
               
              3.9 of 5
              4.0 out of 5.0 Stars

              The rooms outside the inn are undergoing renovations and though our room was redone there was some fine tuning needed. Also, through no fault of the management, we were not placed in the main building. I had sprained my ankle and was put outside the inn. These rooms do not have the expected charm ...

              The Williams Inn ¥14,105
              Reviewed on Jun 2, 2019
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              The Williams Inn

              The Williams Inn

              1090 Main Street, Williamstown, MA
                 
                3.9 of 5
                3.0 out of 5.0 Stars

                Great location- can walk to campus and downtown. Classic hotel with a great breakfast.

                Berkshire Hills Country Inn ¥8,680
                Reviewed on May 20, 2019
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                Berkshire Hills Country Inn

                Berkshire Hills Country Inn

                1146 Cold Spring Road, Williamstown, MA
                   
                  4.3 of 5
                  2.5 out of 5.0 Stars

                  great price for a room in this area. The breakfast was not fancy but very satisfying and the staff at breakfast was sweet as pie!

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