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171 Houses

    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

    Great rentals within 20 miles that match your search

    Distance approx 15.23 km from Spencertown

      24

      Rustic Berkshires Cottage w/ Views of Lake Buel!

      Berkshires / New Marlborough

      New Marlborough cottage

      1 2 7 nights min

      • 1 bedroom
      • sleeps 2
      • 7 nights min
      • Pet Friendly

      Price per night from

      $126

      Responds fast!
      avg. 18 minutes

      Price per night from

      $126

      Distance approx 17.95 km from Spencertown

        19

        The Owls Nest Cabin

        New York / West Coxsackie

        West Coxsackie log cabin

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min
        • Child Friendly
        • Air conditioning
        • Pet Friendly

        Price per night from

        $224

        Price per night from

        $224

        Distance approx 13.88 km from Spencertown

        (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

          $229

          Responds fast!
          avg. 2 hours 34 minutes

          Price per night from

          $229

          Distance approx 2.17 km from Spencertown 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

            $1,374

            Price per night from

            $1,374

            Distance approx 16.42 km from Spencertown

              31

              Big Beautiful 7 bedroom 3 bath hot tub pool table

              Berkshires / Pittsfield

              Pittsfield house

              7 18 2 nights min

              • 7 bedrooms
              • sleeps 18
              • 2 nights min
              • Child Friendly
              • Ask about pets

              Price per night from

              $344

              Price per night from

              $344

              Distance approx 15.52 km from Spencertown

                31

                Lakefront house , great lake and mountain views

                Catskill Region / Athens

                Athens house

                4 10 3 nights min

                • 4 bedrooms
                • sleeps 10
                • 3 nights min
                • Beach / lakeside relaxation
                • Swimming pool
                • Child Friendly

                Price per night from

                $359

                Price per night from

                $359

                Distance approx 10.29 km from Spencertown Show on Map

                  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

                  $458

                  Price per night from

                  $458

                  Distance approx 19.05 km from Spencertown

                  (1) Excellent 

                    20

                    Renovated Barn

                    Connecticut / Taconic

                    Taconic house

                    3 6 2 nights min

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

                    Price per night from

                    $401

                    Responds fast!
                    avg. 32 minutes

                    Price per night from

                    $401

                    Distance approx 6.84 km from Spencertown

                    (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

                      $377

                      Price per night from

                      $377

                      Distance approx 13.64 km from Spencertown

                        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

                        $166

                        Price per night from

                        $166

                        Distance approx 15.59 km from Spencertown

                          18

                          Gracious 3-BR Garden Apt. in the Heart of Hudson

                          New York / Hudson

                          Hudson apartment

                          3 6 2 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 2 nights min
                          • Child Friendly
                          • Car not necessary
                          • Air conditioning

                          Price per night from

                          $287

                          Price per night from

                          $287

                          Distance approx 8.3 km from Spencertown

                            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 17.3 km from Spencertown

                              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

                              $458

                              Price per night from

                              $458

                              Distance approx 19.35 km from Spencertown

                              (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

                                $166

                                Price per night from

                                $166

                                Distance approx 10.63 km from Spencertown

                                (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 11.99 km from Spencertown

                                    12

                                    Tanglewood / Berkshires - 2 Bed 2 Bath Apartment

                                    Berkshires / Lee

                                    Lee apartment

                                    2 6 2 nights min

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

                                    Price per night from

                                    $430

                                    Price per night from

                                    $430

                                    Distance approx 15.18 km from Spencertown

                                    (1) Excellent 

                                      10

                                      Romantic Berkshire Cottage on Storybook Estate

                                      Berkshires / Tyringham

                                      Tyringham cottage

                                      1 2 2 nights min

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

                                      Price per night from

                                      $258

                                      Responds fast!
                                      avg. 1 hour 29 minutes

                                      Price per night from

                                      $258

                                      Distance approx 11.82 km from Spencertown

                                        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

                                        $859

                                        Responds fast!
                                        avg. 47 minutes

                                        Price per night from

                                        $859

                                        Distance approx 11.49 km from Spencertown

                                        (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 17.59 km from Spencertown

                                            7

                                            Berkshires Cottage Country Retreat

                                            New York / Stephentown

                                            Stephentown cottage

                                            3 6 2 nights min

                                            • 3 bedrooms
                                            • sleeps 6
                                            • 2 nights min
                                            • Private garden

                                            Price per night from

                                            $189

                                            Responds fast!
                                            avg. 2 hours 19 minutes

                                            Price per night from

                                            $189

                                            Distance approx 10.48 km from Spencertown

                                              26

                                              3BD Newly Rennovated Contempoary Near Stockbridge

                                              Berkshires / Stockbridge

                                              Stockbridge house

                                              3 6 min stay varies

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

                                              Price per night from

                                              $344

                                              Price per night from

                                              $344

                                              Distance approx 15.1 km from Spencertown

                                              (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 17.85 km from Spencertown

                                                  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 11.33 km from Spencertown

                                                    23

                                                    Renovated 2 bedroom in Heart of Lenox

                                                    Berkshires / Lenox

                                                    Lenox apartment

                                                    2 4 1 night min

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • 1 night min
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $344

                                                    Price per night from

                                                    $344

                                                    Distance approx 12.64 km from Spencertown

                                                      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 7.89 km from Spencertown

                                                        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

                                                        $573

                                                        Price per night from

                                                        $573

                                                        Distance approx 19.49 km from Spencertown

                                                          9

                                                          Larger Than Life 1 BR Sleeps 8 Bentley Brook Resort

                                                          Berkshires / Hancock

                                                          Hancock condo

                                                          1 8 3 nights min

                                                          • 1 bedroom
                                                          • sleeps 8
                                                          • 3 nights min
                                                          • Child Friendly

                                                          Price per night from

                                                          $516

                                                          Price per night from

                                                          $516

                                                          Distance approx 19.88 km from Spencertown

                                                            6

                                                            Thanksgiving week lux condo/4 Berkshires

                                                            Berkshires / Williamstown

                                                            Williamstown condo

                                                            2 4 7 nights min

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

                                                            Price per night from

                                                            $263

                                                            Price per night from

                                                            $263

                                                            Distance approx 4.84 km from Spencertown Show on Map

                                                            (1) Excellent 

                                                              22

                                                              Berkshire Getaway at 'Tofu'S Retreat'

                                                              Berkshires / Alford

                                                              Alford chateau

                                                              3 6 7 nights min

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

                                                              Price per night from

                                                              $247

                                                              Responds fast!
                                                              avg. 1 hour 10 minutes

                                                              Price per night from

                                                              $247

                                                              Distance approx 11.74 km from Spencertown

                                                              (3) Very Good 

                                                                25

                                                                Stunning New Construction All SeasonLakefront Home

                                                                New York / Valatie

                                                                Valatie house

                                                                3 5 7 nights min

                                                                • 3 bedrooms
                                                                • sleeps 5
                                                                • 7 nights min
                                                                • Beach / lakeside relaxation
                                                                • Child Friendly
                                                                • Air conditioning
                                                                “Fantastic House -- Lake, Poor” Yes, the house is wonderful. Beautiful views abound, it's well stocked with everything you'd want, and extremely clean. A five-star place. That said, the lake's dreadful, in our opinion. It's murky-black. We did go s
                                                                …see more

                                                                Price per night from

                                                                $279

                                                                Price per night from

                                                                $279

                                                                Distance approx 13.26 km from Spencertown

                                                                  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

                                                                  $504

                                                                  Price per night from

                                                                  $504

                                                                  Distance approx 15.59 km from Spencertown

                                                                    20

                                                                    Blue SKies

                                                                    New York / Hudson

                                                                    Hudson apartment

                                                                    3 7 2 nights min

                                                                    • 3 bedrooms
                                                                    • sleeps 7
                                                                    • 2 nights min
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $287

                                                                    Price per night from

                                                                    $287

                                                                    Distance approx 10.6 km from Spencertown

                                                                      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

                                                                      Distance approx 16.89 km from Spencertown

                                                                        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 15.37 km from Spencertown

                                                                          18

                                                                          1 Bedroom Hudson Valley Farm House

                                                                          New York / Craryville

                                                                          Craryville guest house

                                                                          1 2 2 nights min

                                                                          • 1 bedroom
                                                                          • sleeps 2
                                                                          • 2 nights min
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $367

                                                                          Price per night from

                                                                          $367

                                                                          Distance approx 15.37 km from Spencertown

                                                                            18

                                                                            4 Bedroom Hudson Valley Farm House

                                                                            New York / Craryville

                                                                            Craryville guest house

                                                                            4 8 2 nights min

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

                                                                            Price per night from

                                                                            $367

                                                                            Price per night from

                                                                            $367

                                                                            Distance approx 18.82 km from Spencertown

                                                                              13

                                                                              Limekiln Farm, historic farmhouse, sleeps up to 6

                                                                              New York / West Coxsackie

                                                                              West Coxsackie farmhouse

                                                                              3 6 1 night min

                                                                              • 3 bedrooms
                                                                              • sleeps 6
                                                                              • 1 night min
                                                                              • Child Friendly
                                                                              • Ask about pets

                                                                              Price per night from

                                                                              $401

                                                                              Price per night from

                                                                              $401