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Berkshires Cottage Rentals(57)

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Berkshires weekend getaway. Stunning View. Walk to lake & downtown.
    4 Bedrooms,
  • 3 Bathrooms, 
  • 1 Half Bath
    • , Sleeps 12
$450 - $600
per night

Berkshires weekend getaway. Stunning View. Walk to lake & downtown.

2 night Minimum Stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
  1. Berkshires >
  2. Great Barrington Cottage
#414235vb
    (9)
    Ashintully Cottage in spectacular setting
      4 Bedrooms,
    • 2 Bathrooms, 
    • 1 Half Bath
      • , Sleeps 7
    $250
    per night

    Ashintully Cottage in spectacular setting

    Book it Now!
    2 night Minimum Stay
    • 4 BR,
    • 2 BA,
    • 1 HF BA,
    • Sleeps 7
    1. Berkshires >
    2. Tyringham Cottage
    #3023396
      2 Reviews
      Newly Renovated Stone Cottage - Walk to Williamstown
        3 Bedrooms,
      • 1 Bathroom
        • , Sleeps 6
      $125 - $300
      per night

      Newly Renovated Stone Cottage - Walk to Williamstown

      3 - 7 night Minimum Stay
      • 3 BR,
      • 1 BA,
      • Sleeps 6
      1. Berkshires >
      2. Williamstown Cottage
      #238090
        (26)
        Charming cottage, near beautiful Lake Buel, child and pet friendly
          4 Bedrooms, Sleeps 7
        $225
        per night

        Charming cottage, near beautiful Lake Buel, child and pet friendly

        2 night Minimum Stay
        • 4 BR,
        • Sleeps 7
        1. Berkshires >
        2. Great Barrington Cottage
        #171589
          (14)
          Charming historic cottage on scenic road to Mt. Greylock
            2 Bedrooms,
          • 1 Bathroom
            • , Sleeps 6
          $110 - $180
          per night

          Charming historic cottage on scenic road to Mt. Greylock

          2 night Minimum Stay
          • 2 BR,
          • 1 BA,
          • Sleeps 6
          1. Berkshires >
          2. Lanesboro Cottage
          #300900
            (100)
            Peaceful pet friendly retreat
              2 Bedrooms,
            • 1 Bathroom
              • , Sleeps 3
            $110 - $120
            per night

            Peaceful pet friendly retreat

            Book it Now!
            2 night Minimum Stay
            • 2 BR,
            • 1 BA,
            • Sleeps 3
            1. Berkshires >
            2. Plainfield Cottage
            #3499348
              Berkshires Cottage Nestled In The Woods Within One Minute Of Tranquil Lake.
                2 Bedrooms,
              • 1 Bathroom
                • , Sleeps 6
              $150 - $195
              per night

              Berkshires Cottage Nestled In The Woods Within One Minute Of Tranquil Lake.

              2 night Minimum Stay
              • 2 BR,
              • 1 BA,
              • Sleeps 6
              1. Berkshires >
              2. Becket Cottage
              #980198
                (6)
                Serene, Private Waterfront Cottage --Perfect Summer Retreat!
                  2 Bedrooms,
                • 2 Bathrooms
                  • , Sleeps 6
                $129 - $175
                per night

                Serene, Private Waterfront Cottage --Perfect Summer Retreat!

                2 - 7 night Minimum Stay
                • 2 BR,
                • 2 BA,
                • Sleeps 6
                1. Berkshires >
                2. Becket Cottage
                #293009
                  (15)
                  Enjoy a complimentary gift basket at our cozy cottage with beautiful lake views
                    2 Bedrooms,
                  • 1 Bathroom
                    • , Sleeps 4
                  $700 - $850
                  per week

                  Enjoy a complimentary gift basket at our cozy cottage with beautiful lake views

                  2 night Minimum Stay
                  • 2 BR,
                  • 1 BA,
                  • Sleeps 4
                  1. Berkshires >
                  2. Hinsdale Cottage
                  #962761
                    (6)
                    Your Vacation Place At West Brook
                      2 Bedrooms,
                    • 1 Bathroom
                      • , Sleeps 6
                    $90 - $125
                    per night

                    Your Vacation Place At West Brook

                    3 night Minimum Stay
                    • 2 BR,
                    • 1 BA,
                    • Sleeps 6
                    1. Jiminy Peak >
                    2. Hancock Cottage
                    #174574
                      Berkshires, Lake Buel, Private Waterfront
                        2 Bedrooms,
                      • 1 Bathroom, 
                      • 1 Half Bath
                        • , Sleeps 6
                      $245 - $250
                      per night

                      Berkshires, Lake Buel, Private Waterfront

                      3 - 7 night Minimum Stay
                      • 2 BR,
                      • 1 BA,
                      • 1 HF BA,
                      • Sleeps 6
                      1. Berkshires >
                      2. Great Barrington Cottage
                      #183642
                        (9)
                        Serenity Stone Cottage on 5 Beautiful Acres in a Historic Town
                          3 Bedrooms,
                        • 2 Bathrooms
                          • , Sleeps 7
                        $880 - $1,080
                        per week

                        Serenity Stone Cottage on 5 Beautiful Acres in a Historic Town

                        7 night Minimum Stay
                        • 3 BR,
                        • 2 BA,
                        • Sleeps 7
                        1. Berkshires >
                        2. Shelburne Falls Cottage
                        #190201
                          (22)
                          Lovely Otis Reservoir Lake Cottage...
                            2 Bedrooms,
                          • 1 Bathroom, 
                          • 1 Half Bath
                            • , Sleeps 5

                          Lovely Otis Reservoir Lake Cottage...

                          • 2 BR,
                          • 1 BA,
                          • 1 HF BA,
                          • Sleeps 5
                          1. Berkshires >
                          2. Otis Cottage
                          #119271
                            (6)
                            Berkshires, Lake Buel, Beautiful Cottage,Walk 2 Private Dock Beach
                              2 Bedrooms,
                            • 1 Bathroom
                              • , Sleeps 6
                            $175 - $215
                            per night

                            Berkshires, Lake Buel, Beautiful Cottage,Walk 2 Private Dock Beach

                            2 night Minimum Stay
                            • 2 BR,
                            • 1 BA,
                            • Sleeps 6
                            1. Berkshires >
                            2. Great Barrington Cottage
                            #3540285
                              Spectacular views of pastures, lovely amenities and tennis court.
                                3 Bedrooms,
                              • 2 Bathrooms
                                • , Sleeps 6
                              $250 - $300
                              per night

                              Spectacular views of pastures, lovely amenities and tennis court.

                              7 night Minimum Stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 6
                              1. Berkshires >
                              2. South Egremont Cottage
                              #373681
                                2 Reviews
                                Lakeside Living in the Beautiful Berkshires
                                  2 Bedrooms,
                                • 1 Bathroom
                                  • , Sleeps 7
                                $120
                                per night

                                Lakeside Living in the Beautiful Berkshires

                                2 night Minimum Stay
                                • 2 BR,
                                • 1 BA,
                                • Sleeps 7
                                1. Berkshires >
                                2. Richmond Cottage
                                #310698
                                  Charming Lakeview Home Near All Activities -- July Now Available
                                    3 Bedrooms,
                                  • 2 Bathrooms
                                    • , Sleeps 8
                                  $125 - $150
                                  per night

                                  Charming Lakeview Home Near All Activities -- July Now Available

                                  2 - 7 night Minimum Stay
                                  • 3 BR,
                                  • 2 BA,
                                  • Sleeps 8
                                  1. Berkshires >
                                  2. Monterey Cottage
                                  #137922
                                    2 Reviews
                                    Charming Waterfront Cottage in the Berkshires
                                      3 Bedrooms,
                                    • 1 Bathroom
                                      • , Sleeps 6
                                    $600 - $975
                                    per week

                                    Charming Waterfront Cottage in the Berkshires

                                    2 - 7 night Minimum Stay
                                    • 3 BR,
                                    • 1 BA,
                                    • Sleeps 6
                                    1. Berkshires >
                                    2. Hinsdale Cottage
                                    #124600
                                      (5)
                                      Tranquil Waterfront Lenox Cottage, min to Tanglewood/Village Berkshire
                                        2 Bedrooms,
                                      • 1 Bathroom, 
                                      • 1 Half Bath
                                        • , Sleeps 4
                                      $1,100 - $1,500
                                      per week

                                      Tranquil Waterfront Lenox Cottage, min to Tanglewood/Village Berkshire

                                      7 night Minimum Stay
                                      • 2 BR,
                                      • 1 BA,
                                      • 1 HF BA,
                                      • Sleeps 4
                                      1. Berkshires >
                                      2. Lenox Cottage
                                      #157193
                                        (8)
                                        Charming Cottage, Village Green in the Berkshires
                                          2 Bedrooms,
                                        • 1 Bathroom
                                          • , Sleeps 4
                                        $200
                                        per night

                                        Charming Cottage, Village Green in the Berkshires

                                        2 night Minimum Stay
                                        • 2 BR,
                                        • 1 BA,
                                        • Sleeps 4
                                        1. Berkshires >
                                        2. New Marlborough Cottage
                                        #214201
                                          (5)
                                          Lakefront Cottage in the Tranquil Berkshires
                                            2 Bedrooms,
                                          • 1 Bathroom
                                            • , Sleeps 6
                                          $1,250
                                          per week

                                          Lakefront Cottage in the Tranquil Berkshires

                                          7 night Minimum Stay
                                          • 2 BR,
                                          • 1 BA,
                                          • Sleeps 6
                                          1. Berkshires >
                                          2. Becket Cottage
                                          #230313
                                            2 Reviews
                                            Charming Cottage, Private Lenox Location
                                              4 Bedrooms,
                                            • 2 Bathrooms
                                              • , Sleeps 8
                                            $1,200 - $1,600
                                            per week

                                            Charming Cottage, Private Lenox Location

                                            3 - 7 night Minimum Stay
                                            • 4 BR,
                                            • 2 BA,
                                            • Sleeps 8
                                            1. Berkshires >
                                            2. Lenox Cottage
                                            #121670
                                              1 Review
                                              Quaint and Quiet Cottage with Lake Rights and Private Dock
                                                2 Bedrooms,
                                              • 1 Bathroom
                                                • , Sleeps 6

                                              Quaint and Quiet Cottage with Lake Rights and Private Dock

                                              • 2 BR,
                                              • 1 BA,
                                              • Sleeps 6
                                              1. Berkshires >
                                              2. Huntington Cottage
                                              #159704
                                                (8)
                                                Hilltop Cottage with Pool & Fireplace
                                                  2 Bedrooms,
                                                • 1 Bathroom, 
                                                • 1 Half Bath
                                                  • , Sleeps 6

                                                Hilltop Cottage with Pool & Fireplace

                                                • 2 BR,
                                                • 1 BA,
                                                • 1 HF BA,
                                                • Sleeps 6
                                                1. Berkshires >
                                                2. Tyringham Cottage
                                                #118310
                                                  Woodland cottage, lake access, 10 minutes from Lenox/Tanglewood, dog friendly
                                                    2 Bedrooms,
                                                  • 1 Bathroom
                                                    • , Sleeps 6

                                                  Woodland cottage, lake access, 10 minutes from Lenox/Tanglewood, dog friendly

                                                  • 2 BR,
                                                  • 1 BA,
                                                  • Sleeps 6
                                                  1. Berkshires >
                                                  2. Richmond Cottage
                                                  #230835
                                                    LUCKY LAST MINUTE GETAWAY SPECIAL...$777.00 PER WEEK
                                                      3 Bedrooms,
                                                    • 1 Bathroom
                                                      • , Sleeps 4

                                                    LUCKY LAST MINUTE GETAWAY SPECIAL...$777.00 PER WEEK

                                                    • 3 BR,
                                                    • 1 BA,
                                                    • Sleeps 4
                                                    1. Berkshires >
                                                    2. Becket Cottage
                                                    #191122
                                                      Charming Cottage in Woods with Tennis & Pond
                                                        3 Bedrooms,
                                                      • 1 Bathroom, 
                                                      • 1 Half Bath
                                                        • , Sleeps 6

                                                      Charming Cottage in Woods with Tennis & Pond

                                                      • 3 BR,
                                                      • 1 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 6
                                                      1. Berkshires >
                                                      2. Lee Cottage
                                                      #101846
                                                        Berkshire Lake Cottage, Town & Attractions Nearby
                                                          2 Bedrooms,
                                                        • 1 Bathroom
                                                          • , Sleeps 6

                                                        Berkshire Lake Cottage, Town & Attractions Nearby

                                                        • 2 BR,
                                                        • 1 BA,
                                                        • Sleeps 6
                                                        1. Berkshires >
                                                        2. Great Barrington Cottage
                                                        #108941
                                                          (13)
                                                          SUMMER SEASON/$10,000 OR $4,500/MO...PERFECTION!
                                                            2 Bedrooms,
                                                          • 3 Bathrooms
                                                            • , Sleeps 6
                                                          $2,200 - $4,500
                                                          per month

                                                          SUMMER SEASON/$10,000 OR $4,500/MO...PERFECTION!

                                                          28 - 272 night Minimum Stay
                                                          • 2 BR,
                                                          • 3 BA,
                                                          • Sleeps 6
                                                          1. Berkshires >
                                                          2. Sheffield Cottage
                                                          #333277
                                                            Ski Cottage at the Meadow's Edge; see Special Season Rate
                                                              3 Bedrooms,
                                                            • 1 Bathroom, 
                                                            • 1 Half Bath
                                                              • , Sleeps 7

                                                            Ski Cottage at the Meadow's Edge; see Special Season Rate

                                                            • 3 BR,
                                                            • 1 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 7
                                                            1. Jiminy Peak >
                                                            2. Hancock Cottage
                                                            #172656
                                                              1 Review
                                                              • 1 - 30 of 57
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