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99 Houses

    22

    BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

    Berkshires / Otis

    Otis house

    6 14 7 nights min

    • 6 bedrooms
    • sleeps 14
    • 7 nights min
    • Ask about children
    • Ask about pets

    Price per night from

    $687

    Price per night from

    $687

      24

      East Otis Reservoir Cabin w/ Porch - Walk to Lake!

      Berkshires / Otis

      Otis log cabin

      2 4 3 nights min

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

      Price per night from

      $115

      Responds fast!
      avg. 11 minutes

      Price per night from

      $115

      Great rentals within 20 miles that match your search

      Distance approx 9.77 km from Otis

      (4) Excellent 

        24

        Waterfront Cottage - 10 Mins to Great Barrington!

        Berkshires / New Marlborough

        New Marlborough cottage

        2 4 min stay varies

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

        Price per night from

        $207

        Responds fast!
        avg. 11 minutes

        Price per night from

        $207

        Distance approx 18.96 km from Otis

        (1) Excellent 

          37

          Charming 2+2 Lakeside Cottage on Best Lake in CT

          Connecticut / Salisbury

          Salisbury cottage

          2 4 30 nights min

          • 2 bedrooms
          • sleeps 4
          • 30 nights min
          • Beach / lakeside relaxation
          • Child Friendly

          Price per night from

          $207

          Price per night from

          $207

          Distance approx 2.73 km from Otis Show on Map

          (1) Excellent 

            20

            Enjoy horses and the largest recreational lake in Massachusetts

            Berkshires / East Otis

            East Otis apartment

            1 4 1 night min

            • 1 bedroom
            • sleeps 4
            • 1 night min
            • Beach / lakeside relaxation
            • Child Friendly
            • Air conditioning

            Price per night from

            $126

            Price per night from

            $126

            Distance approx 5.22 km from Otis Show on Map

              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

              $344

              Responds fast!
              avg. 12 minutes

              Price per night from

              $344

              Distance approx 18.84 km from Otis

              (4) Excellent 

                10

                Great Vacation House in the Berkshires on Richmond Pond

                Berkshires / Richmond

                Richmond house

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Beach / lakeside relaxation
                • Child Friendly
                • Air conditioning

                Price per night from

                $213

                Price per night from

                $213

                Distance approx 19.53 km from Otis

                (1) Excellent 

                  18

                  Hillhouse Log Cabin

                  New York / Hillsdale

                  Hillsdale log cabin

                  3 13 2 nights min

                  • 3 bedrooms
                  • sleeps 13
                  • 2 nights min
                  • Beach / lakeside relaxation
                  • Child Friendly
                  • Air conditioning
                  “rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfe
                  …see more

                  Price per night from

                  $487

                  Price per night from

                  $487

                  Distance approx 13.84 km from Otis

                    13

                    Designer Loft Style Residence

                    Berkshires / Sheffield

                    Sheffield house

                    3 6 7 nights min

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

                    Price per night from

                    $516

                    Responds fast!
                    avg. 3 hours 46 minutes

                    Price per night from

                    $516

                    Distance approx 14.84 km from Otis

                      24

                      NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!

                      Berkshires / Lenox

                      Lenox house

                      3 6 3 nights min

                      • 3 bedrooms
                      • sleeps 6
                      • 3 nights min
                      • Child Friendly

                      Price per night from

                      $430

                      Responds fast!
                      avg. 11 minutes

                      Price per night from

                      $430

                      Distance approx 14 km from Otis

                      (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

                        $430

                        Responds fast!
                        avg. 3 hours 22 minutes

                        Price per night from

                        $430

                        Distance approx 19.37 km from Otis

                          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

                          $458

                          Price per night from

                          $458

                          Distance approx 15.32 km from Otis

                          (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 18 minutes

                            Price per night from

                            $115

                            Distance approx 14.5 km from Otis

                            (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 36 minutes

                              Price per night from

                              $745

                              Distance approx 15.11 km from Otis

                                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

                                Distance approx 13.99 km from Otis

                                (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

                                  $344

                                  Price per night from

                                  $344

                                  Distance approx 17.81 km from Otis

                                    32

                                    RIVERSONG "PENTHOUSE"

                                    Berkshires / North Egremont

                                    North Egremont room

                                    1 2 1 night min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 1 night min
                                    • Air conditioning
                                    • Private garden

                                    Price per night from

                                    $160

                                    Responds fast!
                                    avg. 34 minutes

                                    Price per night from

                                    $160

                                    Distance approx 12.14 km from Otis

                                    (1) Excellent 

                                      13

                                      The Gatehouse on Golden Hill

                                      Berkshires / Lee

                                      Lee house

                                      4 14 3 nights min

                                      • 4 bedrooms
                                      • sleeps 14
                                      • 3 nights min
                                      • Child Friendly
                                      • Air conditioning
                                      • Private garden

                                      Price per night from

                                      $915

                                      Price per night from

                                      $915

                                      Distance approx 14.9 km from Otis

                                      (2) Excellent 

                                        10

                                        Heart of Lenox

                                        Berkshires / Lenox

                                        Lenox house

                                        2 4 2 nights min

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

                                        Price per night from

                                        $201

                                        Responds fast!
                                        avg. 2 hours 17 minutes

                                        Price per night from

                                        $201

                                        Distance approx 11.75 km from Otis

                                        (2) Very Good 

                                          12

                                          Berkshires Spacious Comfortable Charming Farmhouse

                                          Berkshires / Lee

                                          Lee apartment

                                          3 8 2 nights min

                                          • 3 bedrooms
                                          • sleeps 8
                                          • 2 nights min
                                          • Child Friendly
                                          • Air conditioning
                                          “lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.
                                          …see more

                                          Price per night from

                                          $344

                                          Responds fast!
                                          avg. 1 hour 42 minutes

                                          Price per night from

                                          $344

                                          Distance approx 14.55 km from Otis

                                          (1) Excellent 

                                            24

                                            Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu

                                            Berkshires / Stockbridge

                                            Stockbridge cottage

                                            2 4 min stay varies

                                            • 2 bedrooms
                                            • sleeps 4
                                            • min stay varies
                                            • Air conditioning

                                            Price per night from

                                            $343

                                            Responds fast!
                                            avg. 13 minutes

                                            Price per night from

                                            $343

                                            Distance approx 9.33 km from Otis

                                              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

                                              $229

                                              Responds fast!
                                              avg. 36 minutes

                                              Price per night from

                                              $229

                                              Distance approx 16.22 km from Otis

                                              (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

                                                $298

                                                Price per night from

                                                $298

                                                Distance approx 7.51 km from Otis Show on Map

                                                  9

                                                  Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

                                                  Berkshires / Tyringham

                                                  Tyringham house

                                                  1 4 2 nights min

                                                  • 1 bedroom
                                                  • sleeps 4
                                                  • 2 nights min
                                                  • Ask about children
                                                  • Ask about pets

                                                  Price per night from

                                                  $287

                                                  Responds fast!
                                                  avg. 1 hour 29 minutes

                                                  Price per night from

                                                  $287

                                                  Distance approx 9.33 km from Otis

                                                  (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

                                                    $201

                                                    Responds fast!
                                                    avg. 36 minutes

                                                    Price per night from

                                                    $201

                                                    Distance approx 11.33 km from Otis

                                                      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 14.68 km from Otis

                                                        19

                                                        One of the Finest Homes and Best location in the Berkshires

                                                        Berkshires / Stockbridge

                                                        Stockbridge house

                                                        4 10 2 nights min

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • 2 nights min
                                                        • Child Friendly
                                                        • Air conditioning
                                                        • Pet Friendly

                                                        Price per night from

                                                        $802

                                                        Price per night from

                                                        $802

                                                        Distance approx 9.33 km from Otis

                                                        (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

                                                          $166

                                                          Responds fast!
                                                          avg. 36 minutes

                                                          Price per night from

                                                          $166

                                                          Distance approx 14.76 km from Otis

                                                            4

                                                            Horse Room

                                                            Berkshires / Stockbridge

                                                            Stockbridge farmhouse

                                                            1 3 1 night min

                                                            • 1 bedroom
                                                            • sleeps 3
                                                            • 1 night min
                                                            • Child Friendly
                                                            • Pet Friendly
                                                            • Private garden

                                                            Price per night from

                                                            $172

                                                            Price per night from

                                                            $172

                                                            Distance approx 11.37 km from Otis

                                                            (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

                                                              $86

                                                              Price per night from

                                                              $86

                                                              Distance approx 14.6 km from Otis

                                                                24

                                                                NEW! House w/ Kayak - Walk to Stockbridge Bowl!

                                                                Berkshires / Lenox

                                                                Lenox house

                                                                3 6 min stay varies

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Ski
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $212

                                                                Responds fast!
                                                                avg. 11 minutes

                                                                Price per night from

                                                                $212

                                                                Distance approx 14.71 km from Otis

                                                                  4

                                                                  Nasturtium Room

                                                                  Berkshires / Stockbridge

                                                                  Stockbridge farmhouse

                                                                  1 3 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 3
                                                                  • 1 night min
                                                                  • Child Friendly
                                                                  • Pet Friendly
                                                                  • Private garden

                                                                  Price per night from

                                                                  $172

                                                                  Price per night from

                                                                  $172

                                                                  Distance approx 14.94 km from Otis

                                                                    24

                                                                    NEW-Norfolk Countryside Home 30 Min to Ski Sundown

                                                                    Connecticut / Norfolk

                                                                    Norfolk house

                                                                    4 5 min stay varies

                                                                    • 4 bedrooms
                                                                    • sleeps 5
                                                                    • min stay varies
                                                                    • Ski
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $247

                                                                    Responds fast!
                                                                    avg. 11 minutes

                                                                    Price per night from

                                                                    $247

                                                                    Distance approx 10.45 km from Otis

                                                                      17

                                                                      Picturesque 19th century home on 3 private acres

                                                                      Berkshires / New Marlborough

                                                                      New Marlborough house

                                                                      4 7 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 7
                                                                      • min stay varies
                                                                      • Child Friendly
                                                                      • Private garden

                                                                      Price per night from

                                                                      $172

                                                                      Price per night from

                                                                      $172

                                                                      Distance approx 14.9 km from Otis

                                                                        7

                                                                        Church Street Condo 2B

                                                                        Berkshires / Lenox

                                                                        Lenox apartment

                                                                        2 6 60 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • 60 nights min
                                                                        • Child Friendly
                                                                        • Air conditioning
                                                                        • Pet Friendly

                                                                        Price per night from

                                                                        $107

                                                                        Price per night from

                                                                        $107

                                                                        Distance approx 15.71 km from Otis

                                                                          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

                                                                          $194

                                                                          Responds fast!
                                                                          avg. 11 minutes

                                                                          Price per night from

                                                                          $194

                                                                          Distance approx 11.18 km from Otis

                                                                            23

                                                                            Newly Renovated Berkshire Cottage near Tanglewood

                                                                            Berkshires / Lee

                                                                            Lee cottage

                                                                            1 2 60 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 60 nights min
                                                                            • Nearest beach 5 mi
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $327

                                                                            Responds fast!
                                                                            avg. 13 minutes

                                                                            Price per night from

                                                                            $327

                                                                            Distance approx 14.74 km from Otis

                                                                            (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

                                                                              $327

                                                                              Price per night from

                                                                              $327