West Stockbridge Rentals

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149 Houses

    5

    Cozy Modern Condo for the Berkshires

    Berkshires / West Stockbridge

    West Stockbridge condo

    2 6 1 night min

    • 2 bedrooms
    • sleeps 6
    • 1 night min
    • Child Friendly
    • Air conditioning
    • Pet Friendly

    Price per night from

    $288

    Responds fast!
    avg. 1 hour 23 minutes

    Price per night from

    $288

    (4) Excellent 

      10

      Comfortable Farmhouse in the Berkshires

      Berkshires / West Stockbridge

      West Stockbridge farmhouse

      5 12 2 nights min

      • 5 bedrooms
      • sleeps 12
      • 2 nights min
      • Beach / lakeside relaxation
      • Child Friendly
      • Air conditioning

      Price per night from

      $374

      Price per night from

      $374

      (2) Excellent 

        8

        Cozy & Modern Home -mins from Tanglewood & Kripalu

        Berkshires / West Stockbridge

        West Stockbridge apartment

        2 6 1 night min

        • 2 bedrooms
        • sleeps 6
        • 1 night min
        • Ask about children
        • Air conditioning
        • Ask about pets

        Price per night from

        $115

        Responds fast!
        avg. 1 hour 23 minutes

        Price per night from

        $115

        (7) Excellent 

          18

          To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

          Berkshires / West Stockbridge

          West Stockbridge house

          3 8 min stay varies

          • 3 bedrooms
          • sleeps 8
          • min stay varies
          • Beach / lakeside relaxation
          • Child Friendly
          • Pet Friendly
          “A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits
          …see more

          Price per night from

          $379

          Price per night from

          $379

          (1) Excellent 

            24

            'Butterfly Hill' West Stockbridge Home on 3 Acres!

            Berkshires / West Stockbridge

            West Stockbridge house

            2 4 min stay varies

            • 2 bedrooms
            • sleeps 4
            • min stay varies
            • Ski
            • Child Friendly

            Price per night from

            $189

            Responds fast!
            avg. 58 minutes

            Price per night from

            $189

            (39) Excellent 

              20

              Berkshire Farmhouse Vacation

              Berkshires / West Stockbridge

              West Stockbridge house

              5 12 min stay varies

              • 5 bedrooms
              • sleeps 12
              • min stay varies
              • Nearest beach 2 mi
              • Child Friendly
              • Pet Friendly
              “Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the l
              …see more

              Price per night from

              $300

              Price per night from

              $300

                16

                Beautifully Renovated Berkshires Farmhouse

                Berkshires / West Stockbridge

                West Stockbridge b and b

                2 4 2 nights min

                • 2 bedrooms
                • sleeps 4
                • 2 nights min
                • Air conditioning
                • Private garden

                Price per night from

                $241

                Price per night from

                $241

                Great rentals within 20 miles that match your search

                Distance approx 15.47 km from West Stockbridge

                  18

                  Spacious wooded home

                  Berkshires / Becket

                  Becket house

                  4 12 3 nights min

                  • 4 bedrooms
                  • sleeps 12
                  • 3 nights min
                  • Beach / lakeside relaxation
                  • Private garden

                  Price per night from

                  $225

                  Price per night from

                  $225

                  Distance approx 15.9 km from West Stockbridge

                  (3) Very Good 

                    14

                    2200sf Country House on 16 Acres-2 Miles to Jiminy

                    Berkshires / Hancock

                    Hancock house

                    4 9 2 nights min

                    • 4 bedrooms
                    • sleeps 9
                    • 2 nights min
                    • Child Friendly
                    • Pet Friendly
                    “Great house Jiminy Peak” We (family of 4) stayed a weekend in January 2010 with friends (family of 5). It is a great house, perfect location and the owner is really great to deal with. Highly recommended for everyone with kids. easy drive to the slope
                    …see more

                    Price per night from

                    $259

                    Price per night from

                    $259

                    Distance approx 7.24 km from West Stockbridge Show on Map

                      29

                      Beauty in the Berkshires

                      New York / Austerlitz

                      Austerlitz house

                      6 14 2 nights min

                      • 6 bedrooms
                      • sleeps 14
                      • 2 nights min
                      • Child Friendly

                      Price per night from

                      $1,381

                      Price per night from

                      $1,381

                      Distance approx 17.52 km from West Stockbridge

                      (2) Excellent 

                        14

                        Newly Renovated Lakefront Getaway on Robinson Pond

                        New York / Copake

                        Copake house

                        3 5 3 nights min

                        • 3 bedrooms
                        • sleeps 5
                        • 3 nights min
                        • Beach / lakeside relaxation
                        • Nearest beach 0 mi
                        • Child Friendly

                        Price per night from

                        $230

                        Responds fast!
                        avg. 2 hours 41 minutes

                        Price per night from

                        $230

                        Distance approx 17.42 km from West Stockbridge

                        (5) Excellent 

                          10

                          Apple Cottage

                          Berkshires / Sheffield

                          Sheffield farmhouse

                          3 8 1 night min

                          • 3 bedrooms
                          • sleeps 8
                          • 1 night min
                          • Ask about children
                          • Air conditioning
                          • Private garden

                          Price per night from

                          $432

                          Responds fast!
                          avg. 3 hours 22 minutes

                          Price per night from

                          $432

                          Distance approx 8.75 km from West Stockbridge

                          (24) Excellent 

                            18

                            Berkshires: Romantic Cottage with spectacular view

                            Berkshires / Great Barrington

                            Great Barrington cottage

                            1 3 min stay varies

                            • 1 bedroom
                            • sleeps 3
                            • min stay varies
                            • Nearest beach 2 mi
                            • Swimming pool
                            • Ask about children
                            “Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything loo
                            …see more

                            Price per night from

                            $229

                            Price per night from

                            $229

                            Distance approx 16.98 km from West Stockbridge

                            (13) Very Good 

                              13

                              Quiet Comfortable Cabin 5 Min. Walk to Lake

                              Berkshires / Becket

                              Becket house

                              2 4 2 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 2 nights min
                              • Child Friendly
                              • Air conditioning
                              • Ask about pets
                              “Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby are
                              …see more

                              Price per night from

                              $171

                              Price per night from

                              $171

                              Distance approx 19.1 km from West Stockbridge

                                16

                                Escape to Avalon Cottage in the Hudson Valley

                                New York / Craryville

                                Craryville house

                                3 5 3 nights min

                                • 3 bedrooms
                                • sleeps 5
                                • 3 nights min
                                • Child Friendly

                                Price per night from

                                $167

                                Price per night from

                                $167

                                Distance approx 15.89 km from West Stockbridge

                                  18

                                  Historic Home on 8.5 Acres

                                  Berkshires / Dalton

                                  Dalton house

                                  3 9 3 nights min

                                  • 3 bedrooms
                                  • sleeps 9
                                  • 3 nights min
                                  • Swimming pool
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $461

                                  Price per night from

                                  $461

                                  Distance approx 11.15 km from West Stockbridge

                                    12

                                    Fabulous Post & Beam Berkshire Rental

                                    Berkshires / Monterey

                                    Monterey house

                                    7 21 nights min

                                    • sleeps 7
                                    • 21 nights min
                                    • Ask about children
                                    • Car not necessary
                                    • Ask about pets

                                    Price per night from

                                    $204

                                    Price per night from

                                    $204

                                    Distance approx 16.79 km from West Stockbridge

                                    (1) Excellent 

                                      26

                                      Whitman Woods - A Berkshire Vacation

                                      Berkshires / Hancock

                                      Hancock house

                                      4 8 1 night min

                                      • 4 bedrooms
                                      • sleeps 8
                                      • 1 night min
                                      • Child Friendly
                                      • Private garden

                                      Price per night from

                                      $98

                                      Price per night from

                                      $98

                                      Distance approx 16.94 km from West Stockbridge

                                        28

                                        Country Retreat w/ Pool Near Hip Hudson, NY

                                        New York / Hudson

                                        Hudson house

                                        3 8 3 nights min

                                        • 3 bedrooms
                                        • sleeps 8
                                        • 3 nights min
                                        • Swimming pool
                                        • Child Friendly
                                        • Ask about pets

                                        Price per night from

                                        $461

                                        Price per night from

                                        $461

                                        Distance approx 9.6 km from West Stockbridge

                                          48

                                          Total Privacy! Tanglewood Retreat With Berkshire Views!

                                          New York / Hillsdale

                                          Hillsdale house

                                          5 14 2 nights min

                                          • 5 bedrooms
                                          • sleeps 14
                                          • 2 nights min
                                          • Ask about children

                                          Price per night from

                                          $691

                                          Price per night from

                                          $691

                                          Distance approx 15.98 km from West Stockbridge

                                          (2) Excellent 

                                            16

                                            PanoramicView1000 sq ft Guest Quarters Berkshires

                                            Berkshires / Hancock

                                            Hancock cottage

                                            1 6 2 nights min

                                            • 1 bedroom
                                            • sleeps 6
                                            • 2 nights min
                                            • Child Friendly
                                            • Air conditioning
                                            • Ask about pets

                                            Price per night from

                                            $167

                                            Price per night from

                                            $167

                                            Distance approx 19.25 km from West Stockbridge

                                              16

                                              Olde York Farm Distillery Suite

                                              New York / Claverack

                                              Claverack farmhouse

                                              2 6 1 night min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 1 night min
                                              • Beach / lakeside relaxation
                                              • Child Friendly
                                              • Air conditioning

                                              Price per night from

                                              $286

                                              Price per night from

                                              $286

                                              Distance approx 12.39 km from West Stockbridge

                                                36

                                                Spacious Berkshires Home w/ Pool & Patio!

                                                Berkshires / North Egremont

                                                North Egremont house

                                                5 10 2 nights min

                                                • 5 bedrooms
                                                • sleeps 10
                                                • 2 nights min
                                                • Swimming pool
                                                • Ski
                                                • Child Friendly

                                                Price per night from

                                                $858

                                                Responds fast!
                                                avg. 9 minutes

                                                Price per night from

                                                $858

                                                Distance approx 17.53 km from West Stockbridge

                                                (8) Excellent 

                                                  17

                                                  Outdoor getaway hunting,fishing,skiing..relaxation

                                                  New York / Copake

                                                  Copake house

                                                  3 9 2 nights min

                                                  • 3 bedrooms
                                                  • sleeps 9
                                                  • 2 nights min
                                                  • Beach / lakeside relaxation
                                                  • Nearest beach 8 mi
                                                  • Child Friendly
                                                  “Home Away from Home ~ A great place to gather11” Had family coming from New York, Massachusetts and Connecticut to celebrate my birthday ~ hotels, motels are expensive, and they're not home. This house offered a great place to convene ~ outdoor gas gr
                                                  …see more

                                                  Price per night from

                                                  $219

                                                  Price per night from

                                                  $219

                                                  Distance approx 8.68 km from West Stockbridge

                                                    7

                                                    the BIG room at chestnut lodge

                                                    Berkshires / Lee

                                                    Lee b and b

                                                    1 6 2 nights min

                                                    • 1 bedroom
                                                    • sleeps 6
                                                    • 2 nights min
                                                    • Ask about children
                                                    • Pet Friendly

                                                    Price per night from

                                                    $230

                                                    Responds fast!
                                                    avg. 36 minutes

                                                    Price per night from

                                                    $230

                                                    Distance approx 8.68 km from West Stockbridge

                                                    (1) Excellent 

                                                      8

                                                      Writer's Room at Chestnut Lodge

                                                      Berkshires / Lee

                                                      Lee b and b

                                                      1 2 2 nights min

                                                      • 1 bedroom
                                                      • sleeps 2
                                                      • 2 nights min
                                                      • Nearest beach 8 mi
                                                      • Ask about children
                                                      • Air conditioning

                                                      Price per night from

                                                      $205

                                                      Responds fast!
                                                      avg. 36 minutes

                                                      Price per night from

                                                      $205

                                                      Distance approx 15.53 km from West Stockbridge

                                                        19

                                                        Relaxing Victorian Farmhouse

                                                        New York / Philmont

                                                        Philmont house

                                                        3 4 2 nights min

                                                        • 3 bedrooms
                                                        • sleeps 4
                                                        • 2 nights min
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $225

                                                        Price per night from

                                                        $225

                                                        Distance approx 1.94 km from West Stockbridge Show on Map

                                                          20

                                                          New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

                                                          Berkshires / Richmond

                                                          Richmond house

                                                          3 6 7 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 7 nights min
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $572

                                                          Price per night from

                                                          $572

                                                          Distance approx 6.21 km from West Stockbridge Show on Map

                                                            13

                                                            Garfield House

                                                            Maine / Lee

                                                            Lee apartment

                                                            2 6 2 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 2 nights min
                                                            • Child Friendly
                                                            • Pet Friendly

                                                            Price per night from

                                                            $201

                                                            Price per night from

                                                            $201

                                                            Distance approx 14.63 km from West Stockbridge

                                                              13

                                                              Berkshires Summer Rental Beaver Pond Hancock MA

                                                              Berkshires / Hancock

                                                              Hancock condo

                                                              3 6 30 nights min

                                                              • 3 bedrooms
                                                              • sleeps 6
                                                              • 30 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $115

                                                              Price per night from

                                                              $115

                                                              Distance approx 13.47 km from West Stockbridge

                                                              (3) Excellent 

                                                                11

                                                                Overnight at Althouse -Higgins

                                                                New York / Hillsdale

                                                                Hillsdale apartment

                                                                2 4 2 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 2 nights min
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $202

                                                                Price per night from

                                                                $202

                                                                Distance approx 13 km from West Stockbridge

                                                                  19

                                                                  Berkshire Country Estate - Rose Suite

                                                                  New York / Old Chatham

                                                                  Old Chatham villa

                                                                  2 4 2 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 2 nights min
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $196

                                                                  Price per night from

                                                                  $196

                                                                  Distance approx 9.36 km from West Stockbridge

                                                                    7

                                                                    Deluxe New Home, 2 Master Suites, Tanglewood Area

                                                                    Berkshires / Lee

                                                                    Lee house

                                                                    5 12 3 nights min

                                                                    • 5 bedrooms
                                                                    • sleeps 12
                                                                    • 3 nights min
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $863

                                                                    Price per night from

                                                                    $863

                                                                    Distance approx 16.13 km from West Stockbridge

                                                                    (1) Excellent 

                                                                      14

                                                                      The perfect Southern Berkshire winter vacation esc

                                                                      Berkshires / Sheffield

                                                                      Sheffield house

                                                                      4 10 7 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 10
                                                                      • 7 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $576

                                                                      Price per night from

                                                                      $576

                                                                      Distance approx 16.31 km from West Stockbridge

                                                                        10

                                                                        Red Mapple Farm

                                                                        New York / Malden Bridge

                                                                        Malden Bridge house

                                                                        4 8 4 nights min

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • 4 nights min
                                                                        • Ski
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $507

                                                                        Price per night from

                                                                        $507

                                                                        Distance approx 15.77 km from West Stockbridge

                                                                        (1) Very Good 

                                                                          6

                                                                          Jiminy Peak Ski Resort-Country Village's Best Unit

                                                                          Berkshires / Hancock

                                                                          Hancock apartment

                                                                          2 6 1 night min

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • 1 night min
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $288

                                                                          Responds fast!
                                                                          avg. 16 minutes

                                                                          Price per night from

                                                                          $288

                                                                          Distance approx 18.14 km from West Stockbridge

                                                                            19

                                                                            Charming Berkshires lakefront house, great views

                                                                            Berkshires / Cheshire

                                                                            Cheshire house

                                                                            2 5 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 5
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Car not necessary

                                                                            Price per night from

                                                                            $288

                                                                            Price per night from

                                                                            $288

                                                                            Distance approx 5.75 km from West Stockbridge Show on Map

                                                                              26

                                                                              NEW! Lakefront Berkshires House w/Deck, Dock +Boat

                                                                              Berkshires / Housatonic

                                                                              Housatonic house

                                                                              4 10 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Ski
                                                                              • Child Friendly
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $195

                                                                              Responds fast!
                                                                              avg. 21 minutes

                                                                              Price per night from

                                                                              $195