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Cheap Chesterwood Hotels

Completely Renovated Historic Home in the Heart of the Berkshires

Completely Renovated Historic Home in the Heart of the Berkshires

0.4 km from Chesterwood
     
     

    With a stay at this vacation home in Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Chesterwood.

    Completely Renovated Historic Home in the Heart of the BerkshiresGet Rates

    Stockbridge Country Inn

    Stockbridge Country Inn

    0.3 km from Chesterwood
      4.5 out of 5.0
       
       

      With a stay at Stockbridge Country Inn in Stockbridge, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Chesterwood.

      Stockbridge Country InnGet Rates

      Tranquil 3BR Stockbridge House W/private Deck

      Tranquil 3BR Stockbridge House W/private Deck

      1.3 km from Chesterwood
         
         

        With a stay at this vacation home in West Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Berkshire Botanical Garden.

        Tranquil 3BR Stockbridge House W/private DeckGet Rates

        Cozy Stockbridge Home - Walk To Golf Course!

        Cozy Stockbridge Home - Walk To Golf Course!

        0.6 km from Chesterwood
           
           

          With a stay at this vacation home in Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Mission House.

          Cozy Stockbridge Home - Walk To Golf Course!Get Rates

          Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires

          Gorgeous Home, Nature Lover's Delight in the Heart of the Berkshires

          1.0 km from Chesterwood
             
             

            With a stay at this vacation home in Housatonic, you'll be within a 15-minute drive of Ski Butternut and Chesterwood.

            Gorgeous Home, Nature Lover's Delight in the Heart of the BerkshiresGet Rates

            Tanglewood Suites

            Tanglewood Suites

            0.6 km from Chesterwood
              2.5 out of 5.0
               
               

              When you stay at Tanglewood Suites in Stockbridge, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Ski Butternut.

              Tanglewood SuitesGet Rates

              "too Good" With 11 Private Acres. Contact us for Monthly Specials!

              "too Good" With 11 Private Acres. Contact us for Monthly Specials!

              1.0 km from Chesterwood
                 
                 

                With a stay at this vacation home in Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Ski Butternut.

                "too Good" With 11 Private Acres. Contact us for Monthly Specials!Get Rates

                In-town Victorian Nightly/monthly. 5 Bds $500/nt, 6 Bds $650 or 12 Bds

                In-town Victorian Nightly/monthly. 5 Bds $500/nt, 6 Bds $650 or 12 Bds

                0.5 km from Chesterwood
                   
                   

                  With a stay at this vacation home in Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Ski Butternut.

                  In-town Victorian Nightly/monthly. 5 Bds $500/nt, 6 Bds $650 or 12 BdsGet Rates

                  A Grand Estate in Historic Stockbridge

                  A Grand Estate in Historic Stockbridge

                  0.6 km from Chesterwood
                     
                     

                    With a stay at this vacation home, you'll be centrally located in Stockbridge, within a 15-minute drive of Tanglewood Music Center and Ski Butternut.

                    A Grand Estate in Historic StockbridgeGet Rates

                    Modern New England Farmhouse on Prospect Hill

                    Modern New England Farmhouse on Prospect Hill

                    1.3 km from Chesterwood
                       
                       

                      With a stay at this vacation home in Stockbridge, you'll be in the mountains, within a 15-minute drive of Tanglewood Music Center and Naumkeag.

                      Modern New England Farmhouse on Prospect HillGet Rates

                      The Red Lion Inn

                      The Red Lion Inn

                      0.6 km from Chesterwood
                        3.5 out of 5.0
                         
                         

                        When you stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 15-minute drive of Tanglewood Music Center and Ski ...

                        The Red Lion InnGet Rates

                        Holiday Inn Express Hotel & Suites Great Barrington

                        Holiday Inn Express Hotel & Suites Great Barrington

                        6.0 km from Chesterwood
                          2.5 out of 5.0
                           
                           

                          With a stay at Holiday Inn Express Hotel & Suites Great Barrington in Great Barrington, you'll be on a river, within a 10-minute drive of Ski Butternut and Mahaiwe ...

                          Holiday Inn Express Hotel & Suites Great BarringtonGet Rates

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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.