Canaan Rentals

Close

Enter dates for more accurate prices

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

133 Houses

    9

    Cedar Chest

    New York / Canaan

    Canaan cottage

    1 2 7 nights min

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

    Price per night from

    $115

    Price per night from

    $115

    Great rentals within 20 miles that match your search

    Distance approx 7.2 km from Canaan

      19

      Berkshire Country Estate - Rose Suite

      New York / Old Chatham

      Old Chatham villa

      2 4 2 nights min

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

      Price per night from

      $195

      Price per night from

      $195

      Distance approx 12.92 km from Canaan

        8

        7 night Christmas week Wyndham Bentley Brook 2 bdr condo Slopeside

        Berkshires / Hancock

        Hancock condo

        2 8 7 nights min

        • 2 bedrooms
        • sleeps 8
        • 7 nights min
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $229

        Price per night from

        $229

        Distance approx 10.58 km from Canaan

          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 18.81 km from Canaan

            16

            Olde York Farm Distillery Suite

            New York / Claverack

            Claverack farmhouse

            2 6 1 night min

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

            Price per night from

            $286

            Price per night from

            $286

            Distance approx 12.63 km from Canaan

            (3) Very Good 

              14

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

              Berkshires / Hancock

              Hancock house

              4 9 2 nights min

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

              Price per night from

              $258

              Responds fast!
              avg. 1 hour 34 minutes

              Price per night from

              $258

              Distance approx 10.12 km from Canaan

              (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

                Price per night from

                $279

                Price per night from

                $279

                Distance approx 9.62 km from Canaan

                  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 6.44 km from Canaan

                    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 12.8 km from Canaan

                      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 10.2 km from Canaan

                        22

                        Vacation Home on 10 Acres with Pool and Spa

                        Berkshires / Stockbridge

                        Stockbridge house

                        3 6 7 nights min

                        • 3 bedrooms
                        • sleeps 6
                        • 7 nights min
                        • Child Friendly
                        • Ask about pets

                        Price per night from

                        $859

                        Price per night from

                        $859

                        Distance approx 15.09 km from Canaan

                          10

                          ground floor garden room

                          Berkshires / Lee

                          Lee b and b

                          1 2 2 nights min

                          • 1 bedroom
                          • sleeps 2
                          • 2 nights min
                          • Nearest beach 5 mi
                          • Ask about children
                          • Ask about pets

                          Price per night from

                          $91

                          Responds fast!
                          avg. 36 minutes

                          Price per night from

                          $91

                          Distance approx 7.2 km from Canaan

                            24

                            Beautiful Berkshire Country Estate

                            New York / Old Chatham

                            Old Chatham house

                            8 16 min stay varies

                            • 8 bedrooms
                            • sleeps 16
                            • min stay varies
                            • Swimming pool
                            • Child Friendly
                            • Air conditioning

                            Price per night from

                            $1,031

                            Price per night from

                            $1,031

                            Distance approx 12.64 km from Canaan

                            (1) Very Good 

                              6

                              Jiminy Peak Ski Resort-Country Village's Best Unit

                              Berkshires / Hancock

                              Hancock apartment

                              2 6 1 night min

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

                              Price per night from

                              $287

                              Responds fast!
                              avg. 19 minutes

                              Price per night from

                              $287

                              Distance approx 15.64 km from Canaan

                                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 6.46 km from Canaan

                                (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

                                  Price per night from

                                  $377

                                  Price per night from

                                  $377

                                  Distance approx 17.52 km from Canaan

                                    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 9.81 km from Canaan

                                    (30) Excellent 

                                      21

                                      Gartner House, a charming home in Lenox

                                      Berkshires / Lenox

                                      Lenox apartment

                                      4 7 2 nights min

                                      • 4 bedrooms
                                      • sleeps 7
                                      • 2 nights min
                                      • Child Friendly
                                      • Car not necessary
                                      • Ask about pets
                                      “Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa,

                                      Price per night from

                                      $229

                                      Price per night from

                                      $229

                                      Distance approx 11.17 km from Canaan

                                      (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

                                        Price per night from

                                        $487

                                        Price per night from

                                        $487

                                        Distance approx 9.07 km from Canaan

                                          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 14.63 km from Canaan

                                          (5) Excellent 

                                            31

                                            Berkshires Waterfront Lakehouse Sanctuary

                                            Berkshires / Lanesboro

                                            Lanesboro house

                                            3 6 2 nights min

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

                                            Price per night from

                                            $224

                                            Responds fast!
                                            avg. 3 hours 20 minutes

                                            Price per night from

                                            $224

                                            Distance approx 15.91 km from Canaan

                                              16

                                              Roaring Rapids Cottage

                                              New York / Columbiaville

                                              Columbiaville house

                                              2 5 3 nights min

                                              • 2 bedrooms
                                              • sleeps 5
                                              • 3 nights min
                                              • Nearest beach 3 mi
                                              • Ask about children
                                              • Air conditioning

                                              Price per night from

                                              $287

                                              Price per night from

                                              $287

                                              Distance approx 7.72 km from Canaan

                                                14

                                                Modern Cozy Wooded Retreat

                                                New York / Spencertown

                                                Spencertown house

                                                2 6 30 nights min

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

                                                Price per night from

                                                $153

                                                Price per night from

                                                $153

                                                Distance approx 11.31 km from Canaan

                                                (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

                                                  Distance approx 13.15 km from Canaan

                                                  (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

                                                    $744

                                                    Responds fast!
                                                    avg. 2 hours 46 minutes

                                                    Price per night from

                                                    $744

                                                    Distance approx 14.15 km from Canaan

                                                    (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

                                                      $172

                                                      Responds fast!
                                                      avg. 3 hours 37 minutes

                                                      Price per night from

                                                      $172

                                                      Distance approx 19.37 km from Canaan

                                                        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 12.76 km from Canaan

                                                        (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 8.58 km from Canaan

                                                          (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

                                                            Price per night from

                                                            $298

                                                            Price per night from

                                                            $298

                                                            Distance approx 11.86 km from Canaan

                                                            (1) Excellent 

                                                              17

                                                              Restored 1886 Eyebrow Colonial

                                                              Berkshires / Stockbridge

                                                              Stockbridge house

                                                              2 6 7 nights min

                                                              • 2 bedrooms
                                                              • sleeps 6
                                                              • 7 nights min
                                                              • Child Friendly
                                                              • Air conditioning
                                                              • Private garden

                                                              Price per night from

                                                              $245

                                                              Price per night from

                                                              $245

                                                              Distance approx 13.26 km from Canaan

                                                                10

                                                                Vacation Village in the Berkshires Available July 22-29

                                                                Berkshires / Hancock

                                                                Hancock condo

                                                                2 8 7 nights min

                                                                • 2 bedrooms
                                                                • sleeps 8
                                                                • 7 nights min
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $180

                                                                Price per night from

                                                                $180

                                                                Distance approx 18.23 km from Canaan

                                                                  23

                                                                  Bassinova-on-Hudson

                                                                  New York / Coxsackie

                                                                  Coxsackie villa

                                                                  5 10 2 nights min

                                                                  • 5 bedrooms
                                                                  • sleeps 10
                                                                  • 2 nights min
                                                                  • Child Friendly

                                                                  Price per night from

                                                                  $2,862

                                                                  Price per night from

                                                                  $2,862

                                                                  Distance approx 15.07 km from Canaan

                                                                    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 12.92 km from Canaan

                                                                    (1) Excellent 

                                                                      10

                                                                      Wyndham Bentley Brook Resort Rents-Hancock,MA -Jiminy Peak

                                                                      Berkshires / Hancock

                                                                      Hancock hotel apartment

                                                                      2 8 2 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 8
                                                                      • 2 nights min
                                                                      • Swimming pool
                                                                      • Child Friendly
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $521

                                                                      Price per night from

                                                                      $521

                                                                      Distance approx 12.98 km from Canaan

                                                                        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

                                                                        $4,121

                                                                        Price per night from

                                                                        $4,121

                                                                        Distance approx 13.17 km from Canaan

                                                                          24

                                                                          3BR Lee House w/ Easy Access to Main Street!

                                                                          Berkshires / Lee

                                                                          Lee house

                                                                          3 10 min stay varies

                                                                          • 3 bedrooms
                                                                          • sleeps 10
                                                                          • min stay varies
                                                                          • Ski
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $275

                                                                          Responds fast!
                                                                          avg. 19 minutes

                                                                          Price per night from

                                                                          $275

                                                                          Distance approx 10.31 km from Canaan

                                                                          (1) Excellent 

                                                                            34

                                                                            INTERIOR DESIGNERS BOTANICAL COTTAGE

                                                                            Berkshires / Lenox

                                                                            Lenox cottage

                                                                            1 5 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 5
                                                                            • 2 nights min
                                                                            • Nearest beach 3 mi
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $166

                                                                            Price per night from

                                                                            $166

                                                                            Distance approx 8.85 km from Canaan

                                                                              5

                                                                              Cozy Modern Condo for the Berkshires

                                                                              Berkshires / West Stockbridge

                                                                              West Stockbridge condo

                                                                              2 6 1 night min

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

                                                                              Price per night from

                                                                              $287

                                                                              Responds fast!
                                                                              avg. 1 hour 29 minutes

                                                                              Price per night from

                                                                              $287