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Massachusetts Ski Cottage Rentals(84)

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Beautiful, Bright and Beachy Cottage; Walk to Town and Beach!
    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 5
$1,295 - $2,100
per week

Beautiful, Bright and Beachy Cottage; Walk to Town and Beach!

Book it Now!
7 night Minimum Stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
  1. Martha's Vineyard >
  2. Oak Bluffs Cottage
#229848vb
    2 Reviews
    Cape Cod Summers begin here....sea breezes, bay beach, sun, sand ....SUMMER!
      2 Bedrooms,
    • 1 Bathroom
      • , Sleeps 4
    $225 - $375
    per night

    Cape Cod Summers begin here....sea breezes, bay beach, sun, sand ....SUMMER!

    3 - 7 night Minimum Stay
    • 2 BR,
    • 1 BA,
    • Sleeps 4
    1. Cape Cod >
    2. Wellfleet Cottage
    #954662
      (4)
      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)
        All Season Vacation Home Private Beach Spectacular Ocean Views
          3 Bedrooms,
        • 1 Bathroom, 
        • 1 Half Bath
          • , Sleeps 6
        $150
        per night

        All Season Vacation Home Private Beach Spectacular Ocean Views

        2 night Minimum Stay
        • 3 BR,
        • 1 BA,
        • 1 HF BA,
        • Sleeps 6
        1. Cape Cod >
        2. East Sandwich Cottage
        #981739
          (10)
          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)
              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
                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
                  (97)
                  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)
                    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)
                      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)
                        Short walk to 3 great beaches from private, quiet cottage!
                          3 Bedrooms,
                        • 1 Bathroom
                          • , Sleeps 7
                        $1,700 - $1,900
                        per week

                        Short walk to 3 great beaches from private, quiet cottage!

                        7 night Minimum Stay
                        • 3 BR,
                        • 1 BA,
                        • Sleeps 7
                        1. Merrimack Valley & Essex County >
                        2. Plum Island Cottage
                        #122664
                          169 North Shore Blvd SD231
                            3 Bedrooms,
                          • 1 Bathroom
                            • , Sleeps 6
                          $1,000 - $2,200
                          per week

                          169 North Shore Blvd SD231

                          7 night Minimum Stay
                          • 3 BR,
                          • 1 BA,
                          • Sleeps 6
                          1. Cape Cod >
                          2. East Sandwich Cottage
                          #3214985
                            1 Review
                            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)
                              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
                                Hillside lake house
                                  3 Bedrooms,
                                • 1 Bathroom
                                  • , Sleeps 6
                                $150 - $250
                                per night

                                Hillside lake house

                                2 night Minimum Stay
                                • 3 BR,
                                • 1 BA,
                                • Sleeps 6
                                1. Central Massachusetts >
                                2. Holland Cottage
                                #3009192
                                  2 Reviews
                                  Cozy, Charming, Lovely Gardens, Near Ocean , Family Friendly
                                    2 Bedrooms,
                                  • 1 Bathroom
                                    • , Sleeps 7

                                  Cozy, Charming, Lovely Gardens, Near Ocean , Family Friendly

                                  • 2 BR,
                                  • 1 BA,
                                  • Sleeps 7
                                  1. South Shore Massachusetts >
                                  2. Plymouth Cottage
                                  #316381
                                    (16)
                                    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)
                                      39 Freeman Ave SD207
                                        3 Bedrooms,
                                      • 1 Bathroom
                                        • , Sleeps 6
                                      $1,200 - $2,800
                                      per week

                                      39 Freeman Ave SD207

                                      7 night Minimum Stay
                                      • 3 BR,
                                      • 1 BA,
                                      • Sleeps 6
                                      1. Cape Cod >
                                      2. East Sandwich Cottage
                                      #3209776
                                        99 North Shore Blvd SD135
                                          2 Bedrooms,
                                        • 2 Bathrooms
                                          • , Sleeps 6
                                        $1,000 - $2,200
                                        per week

                                        99 North Shore Blvd SD135

                                        7 night Minimum Stay
                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                        1. Cape Cod >
                                        2. East Sandwich Cottage
                                        #3215413
                                          3 Reviews
                                          Oceanside B SD142
                                            2 Bedrooms,
                                          • 1 Bathroom
                                            • , Sleeps 6
                                          $800 - $1,650
                                          per week

                                          Oceanside B SD142

                                          7 night Minimum Stay
                                          • 2 BR,
                                          • 1 BA,
                                          • Sleeps 6
                                          1. Cape Cod >
                                          2. East Sandwich Cottage
                                          #3243669
                                            3 Reviews
                                            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
                                              15 Freedom Rd
                                                3 Bedrooms,
                                              • 1 Bathroom, 
                                              • 1 Half Bath
                                                • , Sleeps 6
                                              $1,000 - $1,300
                                              per week

                                              15 Freedom Rd

                                              7 night Minimum Stay
                                              • 3 BR,
                                              • 1 BA,
                                              • 1 HF BA,
                                              • Sleeps 6
                                              1. Cape Cod >
                                              2. Sandwich Cottage
                                              #3525140
                                                2 Reviews
                                                Lakefront Cottage with Private Dock -
                                                  2 Bedrooms,
                                                • 1 Bathroom
                                                  • , Sleeps 6
                                                $165 - $185
                                                per night

                                                Lakefront Cottage with Private Dock -

                                                2 - 7 night Minimum Stay
                                                • 2 BR,
                                                • 1 BA,
                                                • Sleeps 6
                                                1. Central Massachusetts >
                                                2. Douglas Cottage
                                                #985022
                                                  (18)
                                                  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)
                                                    191 A North Shore Blvd. SD146
                                                      2 Bedrooms,
                                                    • 1 Bathroom
                                                      • , Sleeps 4
                                                    $700 - $1,450
                                                    per week

                                                    191 A North Shore Blvd. SD146

                                                    7 night Minimum Stay
                                                    • 2 BR,
                                                    • 1 BA,
                                                    • Sleeps 4
                                                    1. Cape Cod >
                                                    2. East Sandwich Cottage
                                                    #3205171
                                                      2 Reviews
                                                      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
                                                        Huge Game Room! Great getaway for all ages!
                                                          3 Bedrooms,
                                                        • 1 Bathroom, 
                                                        • 1 Half Bath
                                                          • , Sleeps 8
                                                        $165
                                                        per night

                                                        Huge Game Room! Great getaway for all ages!

                                                        3 - 7 night Minimum Stay
                                                        • 3 BR,
                                                        • 1 BA,
                                                        • 1 HF BA,
                                                        • Sleeps 8
                                                        1. Central Massachusetts >
                                                        2. Spencer Cottage
                                                        #294599
                                                          (10)
                                                          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)
                                                            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
                                                              • 1 - 30 of 84
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