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76 Houses

(1) Excellent 

    13

    Lake House

    Connecticut / Lakeville

    Lakeville house

    5 9 2 nights min

    • 5 bedrooms
    • sleeps 9
    • 2 nights min
    • Child Friendly
    • Pet Friendly

    Price per night from

    $690

    Price per night from

    $690

    (3) Excellent 

      42

      4 Bedroom Furnished House in Lakeville Connecticut

      Connecticut / Lakeville

      Lakeville house

      4 8 2 nights min

      • 4 bedrooms
      • sleeps 8
      • 2 nights min
      • Child Friendly
      • Air conditioning
      • Ask about pets

      Price per night from

      $374

      Price per night from

      $374

      Great rentals within 20 miles that match your search

      Distance approx 15.6 km from Lakeville

      (1) Excellent 

        28

        Hudson Valley Cabin - Romantic & Secluded Log Cabin with Private Lake - 85 acres

        New York / Stanfordville

        Stanfordville log cabin

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min

        Price per night from

        $259

        Price per night from

        $259

        Distance approx 17.07 km from Lakeville

        (24) Excellent 

          18

          Berkshires: Romantic Cottage with spectacular view

          Berkshires / Great Barrington

          Great Barrington cottage

          1 3 min stay varies

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

          Price per night from

          $229

          Price per night from

          $229

          Distance approx 14.11 km from Lakeville

            30

            Evergreen Pines Country Estate Villa

            New York / Ancram

            Ancram house

            4 8 1 night min

            • 4 bedrooms
            • sleeps 8
            • 1 night min
            • Beach / lakeside relaxation
            • Swimming pool
            • Child Friendly

            Price per night from

            $2,298

            Price per night from

            $2,298

            Distance approx 19.68 km from Lakeville

              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 4.15 km from Lakeville

              (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 17.8 km from Lakeville

                  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 13.92 km from Lakeville

                    24

                    Prana Residence - Spa

                    Connecticut / Cornwall Bridge

                    Cornwall Bridge house

                    3 7 2 nights min

                    • 3 bedrooms
                    • sleeps 7
                    • 2 nights min
                    • Swimming pool
                    • Ask about children
                    • Air conditioning

                    Price per night from

                    $862

                    Price per night from

                    $862

                    Distance approx 10.27 km from Lakeville

                    (5) Excellent 

                      10

                      Apple Cottage

                      Berkshires / Sheffield

                      Sheffield farmhouse

                      3 8 1 night min

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

                      Price per night from

                      $432

                      Responds fast!
                      avg. 3 hours 22 minutes

                      Price per night from

                      $432

                      Distance approx 12.58 km from Lakeville

                      (8) Excellent 

                        17

                        Outdoor getaway hunting,fishing,skiing..relaxation

                        New York / Copake

                        Copake house

                        3 9 2 nights min

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

                        Price per night from

                        $219

                        Price per night from

                        $219

                        Distance approx 12.52 km from Lakeville

                        (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 13.46 km from Lakeville

                            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 19.88 km from Lakeville

                            (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

                              Distance approx 16.77 km from Lakeville

                              (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

                                Distance approx 17.07 km from Lakeville

                                  8

                                  Guest House on a Trout River w/ Year Round Hot Tub

                                  New York / Red Hook

                                  Red Hook house

                                  1 4 3 nights min

                                  • 1 bedroom
                                  • sleeps 4
                                  • 3 nights min
                                  • Child Friendly
                                  • Pet Friendly

                                  Price per night from

                                  $202

                                  Price per night from

                                  $202

                                  Distance approx 17.43 km from Lakeville

                                    12

                                    Fabulous Post & Beam Berkshire Rental

                                    Berkshires / Monterey

                                    Monterey house

                                    7 21 nights min

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

                                    Price per night from

                                    $204

                                    Price per night from

                                    $204

                                    Distance approx 16.76 km from Lakeville

                                    (14) Excellent 

                                    Certificate of Excellence

                                      55

                                      RiverSong Suite In The Berkshires

                                      Berkshires / North Egremont

                                      North Egremont apartment

                                      1 2 1 night min

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

                                      Certificate of Excellence

                                      Price per night from

                                      $218

                                      Responds fast!
                                      avg. 33 minutes

                                      Price per night from

                                      $218

                                      Distance approx 18.98 km from Lakeville

                                        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

                                        $4,137

                                        Price per night from

                                        $4,137

                                        Distance approx 18.49 km from Lakeville

                                          20

                                          Beautiful Lake House - Magnificent in all 4 Seasons 3 Bed, 2 Bath

                                          Connecticut / Winsted

                                          Winsted house

                                          3 6 min stay varies

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

                                          Price per night from

                                          $259

                                          Responds fast!
                                          avg. 2 hours 31 minutes

                                          Price per night from

                                          $259

                                          Distance approx 13.43 km from Lakeville

                                            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

                                            $214

                                            Responds fast!
                                            avg. 1 hour 16 minutes

                                            Price per night from

                                            $214

                                            Distance approx 15.47 km from Lakeville

                                            (3) Excellent 

                                              11

                                              Overnight at Althouse -Higgins

                                              New York / Hillsdale

                                              Hillsdale apartment

                                              2 4 2 nights min

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

                                              Price per night from

                                              $202

                                              Price per night from

                                              $202

                                              Distance approx 7.09 km from Lakeville

                                                12

                                                The FarmHouse

                                                New York / Millerton

                                                Millerton house

                                                2 5 120 nights min

                                                • 2 bedrooms
                                                • sleeps 5
                                                • 120 nights min

                                                Price per night from

                                                $107

                                                Price per night from

                                                $107

                                                Distance approx 13.61 km from Lakeville

                                                  35

                                                  Charming Private Guest Suite in Historic Village in the Berkshires

                                                  Berkshires / New Marlborough

                                                  New Marlborough studio

                                                  Studio 2 1 night min

                                                  • Studio
                                                  • sleeps 2
                                                  • 1 night min

                                                  Price per night from

                                                  $110

                                                  Price per night from

                                                  $110

                                                  Distance approx 16.31 km from Lakeville

                                                    8

                                                    Kent Victorian Room 4

                                                    Connecticut / Kent

                                                    Kent room

                                                    1 2 2 nights min

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

                                                    Price per night from

                                                    $127

                                                    Price per night from

                                                    $127

                                                    Distance approx 7.47 km from Lakeville

                                                      13

                                                      Quiet Country Contemporary Home on 5 Private Acres

                                                      Connecticut / West Cornwall

                                                      West Cornwall house

                                                      3 10 2 nights min

                                                      • 3 bedrooms
                                                      • sleeps 10
                                                      • 2 nights min
                                                      • Nearest beach 6 mi
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $466

                                                      Price per night from

                                                      $466

                                                      Distance approx 17.94 km from Lakeville

                                                      (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

                                                        Distance approx 16.31 km from Lakeville

                                                          8

                                                          Kent Victorian Room 3

                                                          Connecticut / Kent

                                                          Kent room

                                                          1 2 2 nights min

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

                                                          Price per night from

                                                          $172

                                                          Price per night from

                                                          $172

                                                          Distance approx 6.93 km from Lakeville

                                                            44

                                                            1790 Classic Colonial Center Hall home

                                                            Connecticut / Sharon

                                                            Sharon house

                                                            5 11 2 nights min

                                                            • 5 bedrooms
                                                            • sleeps 11
                                                            • 2 nights min
                                                            • Child Friendly

                                                            Price per night from

                                                            $575

                                                            Price per night from

                                                            $575

                                                            Distance approx 18.96 km from Lakeville

                                                            (6) Excellent 

                                                              12

                                                              The Smith Farm Homestead

                                                              Berkshires / Alford

                                                              Alford b and b

                                                              1 2 2 nights min

                                                              • 1 bedroom
                                                              • sleeps 2
                                                              • 2 nights min
                                                              • Air conditioning
                                                              “Visit Great Barrington, but stay in a true New England town. Cho” Set back in the Berkshires, Alford Ma is a stone's throw from New York State. The small town borders Great Barrington, which is rich in activity. Many famous americans have roamed Bar
                                                              …see more

                                                              Price per night from

                                                              $167

                                                              Responds fast!
                                                              avg. 3 hours 57 minutes

                                                              Price per night from

                                                              $167

                                                              Distance approx 10.5 km from Lakeville

                                                              (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 19.07 km from Lakeville

                                                                  25

                                                                  Lakefront Warren 'Carriage House' on 25 Acres!

                                                                  Connecticut / Warren

                                                                  Warren house

                                                                  7 14 4 nights min

                                                                  • 7 bedrooms
                                                                  • sleeps 14
                                                                  • 4 nights min
                                                                  • Ski
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $1,149

                                                                  Responds fast!
                                                                  avg. 58 minutes

                                                                  Price per night from

                                                                  $1,149

                                                                  Distance approx 15.51 km from Lakeville

                                                                    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 18.73 km from Lakeville

                                                                      32

                                                                      Summer or Summer Monthly Swimming Lake Rhinebeck Oasis

                                                                      New York / Rhinebeck

                                                                      Rhinebeck house

                                                                      3 8 30 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 8
                                                                      • 30 nights min
                                                                      • Child Friendly
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $268

                                                                      Price per night from

                                                                      $268

                                                                      Distance approx 9.85 km from Lakeville

                                                                        4

                                                                        Exclusive Rental in Beautiful Amenia!

                                                                        New York / Amenia

                                                                        Amenia house

                                                                        3 6 30 nights min

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

                                                                        Price per night from

                                                                        $153

                                                                        Price per night from

                                                                        $153

                                                                        Distance approx 14.39 km from Lakeville

                                                                          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

                                                                          $173

                                                                          Price per night from

                                                                          $173

                                                                          Distance approx 19.81 km from Lakeville

                                                                            20

                                                                            Litchfield Hills Hideaway

                                                                            Connecticut / Litchfield

                                                                            Litchfield apartment

                                                                            1 2 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 2
                                                                            • 2 nights min

                                                                            Price per night from

                                                                            $138

                                                                            Responds fast!
                                                                            avg. 3 hours 37 minutes

                                                                            Price per night from

                                                                            $138

                                                                            Distance approx 16.07 km from Lakeville

                                                                              18

                                                                              3 Bedroom Hudson Valley Farm House

                                                                              New York / Craryville

                                                                              Craryville guest house

                                                                              3 6 2 nights min

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

                                                                              Price per night from

                                                                              $368

                                                                              Price per night from

                                                                              $368