Great Barrington Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

126 Houses

(4) Very Good 

    18

    Lakefront Berkshires Ski/Summer House, Great Views

    Berkshires / Great Barrington

    Great Barrington house

    4 10 min stay varies

    • 4 bedrooms
    • sleeps 10
    • min stay varies
    • Beach / lakeside relaxation
    • Child Friendly
    • Pet Friendly

    Price per night from

    $216

    Price per night from

    $216

    (2) Excellent 

      24

      Country Elegance in the Berkshires

      Berkshires / Great Barrington

      Great Barrington house

      4 12 2 nights min

      • 4 bedrooms
      • sleeps 12
      • 2 nights min
      • Nearest beach 0 mi
      • Child Friendly
      • Air conditioning

      Price per night from

      $745

      Responds fast!
      avg. 2 hours 46 minutes

      Price per night from

      $745

      (4) Excellent 

        30

        Gem of the Berkshires, walk to downtown & lake.

        Berkshires / Great Barrington

        Great Barrington house

        5 12 2 nights min

        • 5 bedrooms
        • sleeps 12
        • 2 nights min
        • Nearest beach 0.32 mi
        • Child Friendly
        • Air conditioning
        “Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are b
        …see more

        Price per night from

        $345

        Price per night from

        $345

        (2) Average 

          27

          Shaker Hill

          Berkshires / Great Barrington

          Great Barrington house

          5 10 3 nights min

          • 5 bedrooms
          • sleeps 10
          • 3 nights min
          • Child Friendly
          • Air conditioning

          Price per night from

          $430

          Price per night from

          $430

          (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

            $228

            Price per night from

            $228

              6

              Stunning Home! 120 Acres! Amazing!

              Berkshires / Great Barrington

              Great Barrington house

              9 16 3 nights min

              • 9 bedrooms
              • sleeps 16
              • 3 nights min
              • Swimming pool
              • Child Friendly
              • Air conditioning

              Price per night from

              $4,122

              Price per night from

              $4,122

                15

                S. Berkshires Mountain Treehouse • Views • Privacy

                Berkshires / Great Barrington

                Great Barrington house

                2 4 14 nights min

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

                Price per night from

                $213

                Responds fast!
                avg. 1 hour 16 minutes

                Price per night from

                $213

                (1) Very Good 

                  14

                  Cozy and clean in Gt Barrington- available for October

                  Berkshires / Great Barrington

                  Great Barrington house

                  2 4 3 nights min

                  • 2 bedrooms
                  • sleeps 4
                  • 3 nights min
                  • Nearest beach 2 mi
                  • Child Friendly
                  • Pet Friendly

                  Price per night from

                  $173

                  Responds fast!
                  avg. 3 hours 37 minutes

                  Price per night from

                  $173

                    21

                    Private Berkshire Estate w/Pool & Tennis Court

                    Berkshires / Great Barrington

                    Great Barrington house

                    4 12 min stay varies

                    • 4 bedrooms
                    • sleeps 12
                    • min stay varies
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $659

                    Price per night from

                    $659

                    Great rentals within 20 miles that match your search

                    Distance approx 8.88 km from Great Barrington

                      32

                      Berkshire Home on Lake Garfield w/Dock & Boats

                      Berkshires / Monterey

                      Monterey house

                      4 12 min stay varies

                      • 4 bedrooms
                      • sleeps 12
                      • min stay varies
                      • Ski
                      • Child Friendly
                      • Air conditioning

                      Price per night from

                      $345

                      Responds fast!
                      avg. 58 minutes

                      Price per night from

                      $345

                      Distance approx 9.19 km from Great Barrington Show on Map

                        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

                        Distance approx 15.27 km from Great Barrington

                          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 15.93 km from Great Barrington

                          (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 9.33 km from Great Barrington 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 17.21 km from Great Barrington

                              (1) Excellent 

                                11

                                Riverwood - Cozy Carriage House in the Woods

                                Connecticut / Falls Village

                                Falls Village apartment

                                1 2 2 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 2 nights min
                                • Ask about children
                                • Air conditioning
                                • Private garden

                                Price per night from

                                $259

                                Price per night from

                                $259

                                Distance approx 11.21 km from Great Barrington Show on Map

                                (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 15.48 km from Great Barrington

                                    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 7.92 km from Great Barrington Show on Map

                                      23

                                      Spacious Lakeside Berkshire Home

                                      Berkshires / Monterey

                                      Monterey house

                                      4 10 3 nights min

                                      • 4 bedrooms
                                      • sleeps 10
                                      • 3 nights min
                                      • Child Friendly
                                      • Air conditioning
                                      • Private garden

                                      Price per night from

                                      $460

                                      Price per night from

                                      $460

                                      Distance approx 19.46 km from Great Barrington

                                      (1) Excellent 

                                        21

                                        Berkshire Country Estate - The Library Suite

                                        New York / Old Chatham

                                        Old Chatham house

                                        2 4 2 nights min

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

                                        Price per night from

                                        $173

                                        Price per night from

                                        $173

                                        Distance approx 14.09 km from Great Barrington

                                          6

                                          Berkshires on the Pond

                                          Berkshires / Becket

                                          Becket house

                                          2 2 4 nights min

                                          • 2 bedrooms
                                          • sleeps 2
                                          • 4 nights min
                                          • Nearest beach 16 mi
                                          • Ask about children
                                          • Private garden

                                          Price per night from

                                          $144

                                          Price per night from

                                          $144

                                          Distance approx 17.37 km from Great Barrington

                                            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 14.81 km from Great Barrington

                                              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 17.98 km from Great Barrington

                                                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 3.83 km from Great Barrington Show on Map

                                                  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 10.47 km from Great Barrington Show on Map

                                                  (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

                                                    Distance approx 10.93 km from Great Barrington

                                                      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 11.39 km from Great Barrington

                                                        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 10.93 km from Great Barrington

                                                        (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 14.37 km from Great Barrington

                                                            9

                                                            Cedar Chest

                                                            New York / Canaan

                                                            Canaan cottage

                                                            1 2 7 nights min

                                                            • 1 bedroom
                                                            • sleeps 2
                                                            • 7 nights min
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 2 mi
                                                            • Air conditioning

                                                            Price per night from

                                                            $115

                                                            Price per night from

                                                            $115

                                                            Distance approx 10.93 km from Great Barrington

                                                            (1) Excellent 

                                                              2

                                                              chestnut lodge Queens Room

                                                              Berkshires / Lee

                                                              Lee b and b

                                                              1 2 2 nights min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 2 nights min
                                                              • Ask about pets

                                                              Price per night from

                                                              $167

                                                              Responds fast!
                                                              avg. 36 minutes

                                                              Price per night from

                                                              $167

                                                              Distance approx 9.87 km from Great Barrington

                                                              (1) Excellent 

                                                                10

                                                                Berkshire House Share-The Blue Room

                                                                Berkshires / Lee

                                                                Lee house

                                                                3 2 1 night min

                                                                • 3 bedrooms
                                                                • sleeps 2
                                                                • 1 night min

                                                                Price per night from

                                                                $87

                                                                Price per night from

                                                                $87

                                                                Distance approx 10.75 km from Great Barrington

                                                                  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 19.46 km from Great Barrington

                                                                    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 6.55 km from Great Barrington Show on Map

                                                                    (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 12.56 km from Great Barrington

                                                                        10

                                                                        The Barn at Copake Lake

                                                                        New York / Craryville

                                                                        Craryville barn

                                                                        3 14 2 nights min

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

                                                                        Price per night from

                                                                        $689

                                                                        Price per night from

                                                                        $689

                                                                        Distance approx 4.18 km from Great Barrington 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

                                                                          Distance approx 12.62 km from Great Barrington

                                                                            14

                                                                            Modern Cozy Wooded Retreat

                                                                            New York / Spencertown

                                                                            Spencertown house

                                                                            2 6 30 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • 30 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $153

                                                                            Price per night from

                                                                            $153

                                                                            Distance approx 4.93 km from Great Barrington Show on Map

                                                                            (1) Excellent 

                                                                              20

                                                                              Newly Renovated Colonial on the River! Sleeps 5-6

                                                                              Berkshires / Stockbridge

                                                                              Stockbridge house

                                                                              3 5 3 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 5
                                                                              • 3 nights min
                                                                              • Beach / lakeside relaxation
                                                                              • Child Friendly

                                                                              Price per night from

                                                                              $328

                                                                              Price per night from

                                                                              $328