Vacation Rentals & Cottages in Pickering

Close

Enter dates for more accurate prices

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

1,223 Houses

    14

    BRIAR COTTAGE, open fire, en-suite bedrooms, pet friendly, in Pickering, Ref

    North Yorkshire / Pickering

    Pickering house

    2 4 3 nights min

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

    Price per night from

    $118

    Price per night from

    $118

    (11) Very Good 

      24

      WOODLEA, pet friendly, character holiday cottage, with a garden in Rosedale

      Pickering / Rosedale Abbey

      Rosedale Abbey house

      4 8 3 nights min

      • 4 bedrooms
      • sleeps 8
      • 3 nights min
      • Child Friendly
      • Pet Friendly
      “The Perfect Home away from Home” We stayed at Woodlea for one week, March 9th - 16th, 2012. The home is well-furnished, the decor is welcoming and tasteful, the appliances are quite nice, and the fireplace was glorious. There was a minor plumbing pr

      Price per night from

      $163

      Price per night from

      $163

        21

        LA FENETRE, three floors, open plan accommodation, electric fire, in Pickering

        North Yorkshire / Pickering

        Pickering house

        3 5 3 nights min

        • 3 bedrooms
        • sleeps 5
        • 3 nights min
        • Pet Friendly
        • Private garden

        Price per night from

        $125

        Price per night from

        $125

        (10) Very Good 

          8

          CROFT HEAD COTTAGE, romantic, character holiday cottage, with open fire in

          North Yorkshire / Pickering

          Pickering house

          2 4 3 nights min

          • 2 bedrooms
          • sleeps 4
          • 3 nights min
          • Child Friendly
          • Private garden
          “Brilliant. We wanted to live there forever.” Yorkshire tea on arrival and yummy biscuits were great. Brilliant wood burner.

          Price per night from

          $92

          Price per night from

          $92

          (8) Very Good 

            12

            1 THE OLD METHODIST CHAPEL, family friendly, luxury holiday cottage, with a

            Pickering / Rosedale Abbey

            Rosedale Abbey house

            4 8 3 nights min

            • 4 bedrooms
            • sleeps 8
            • 3 nights min
            • Child Friendly
            “Very satisfactory.” Service excellent.very comfortable very clean.everything you could want in the Chapel.location quite excellent centre for walking and sightseeing. Enjoyed our stay .only things to say had real problems with cooker even though ther

            Price per night from

            $165

            Price per night from

            $165

            (41) Excellent 

              19

              Kings Haven Cottage Pickering North Yorkshire YO18 8AU

              North Yorkshire / Pickering

              Pickering cottage

              1 2 3 nights min

              • 1 bedroom
              • sleeps 2
              • 3 nights min
              • Car not necessary
              • Private garden

              Price per night from

              $85

              Price per night from

              $85

              (3) Excellent 

                9

                MOORS EDGE COTTAGE, pet friendly, country holiday cottage, with open fire in

                Pickering / Rosedale Abbey

                Rosedale Abbey house

                2 4 3 nights min

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

                Price per night from

                $115

                Price per night from

                $115

                  11

                  12 CASTLEGATE, terraced, open fire, private enclosed garden, pet-friendly, in

                  North Yorkshire / Pickering

                  Pickering house

                  2 4 3 nights min

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

                  Price per night from

                  $104

                  Price per night from

                  $104

                  (11) Very Good 

                    10

                    COW BYRE COTTAGE, character holiday cottage, with a garden in Wrelton, Ref 1577

                    North Yorkshire / Pickering

                    Pickering house

                    1 3 3 nights min

                    • 1 bedroom
                    • sleeps 3
                    • 3 nights min
                    • Child Friendly
                    • Private garden
                    “Exactly what we were looking for” Host showed us the accomodation and made themselves available to accomodate any further needs we might have. Clean and had everything we required. Location had everything we were looking for within walking distance or

                    Price per night from

                    $90

                    Price per night from

                    $90

                      10

                      SPIRE VIEW, off road parking, village amenities, WiFi, Pickering, Ref 943752

                      North Yorkshire / Pickering

                      Pickering house

                      1 2 3 nights min

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

                      Price per night from

                      $87

                      Price per night from

                      $87

                        17

                        THE FLOUR POT detached stone cottage, en-suite, WiFi, Pickering, Ref 936971

                        North Yorkshire / Pickering

                        Pickering house

                        1 2 3 nights min

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

                        Price per night from

                        $153

                        Price per night from

                        $153

                        (7) Excellent 

                          10

                          COBBLER'S COTTAGE, pet-friendly, character holiday cottage in Pickering, Ref

                          North Yorkshire / Pickering

                          Pickering house

                          3 5 3 nights min

                          • 3 bedrooms
                          • sleeps 5
                          • 3 nights min
                          • Pet Friendly

                          Price per night from

                          $133

                          Price per night from

                          $133

                          (1) Excellent 

                            11

                            THE HOLLIES, detached, all ground floor, gas fire in sitting room, lovely

                            North Yorkshire / Pickering

                            Pickering house

                            2 4 3 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 3 nights min
                            • Child Friendly
                            • Private garden

                            Price per night from

                            $124

                            Price per night from

                            $124

                              20

                              THE SIDINGS, Grade II listed, off road parking, patio garden, Pickering, Ref

                              North Yorkshire / Pickering

                              Pickering house

                              3 6 3 nights min

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

                              Price per night from

                              $129

                              Price per night from

                              $129

                              (2) Excellent 

                                13

                                31 OUTGANG ROAD, wood burner, ceiling beams, pet friendly, in Pickering, Ref

                                North Yorkshire / Pickering

                                Pickering house

                                1 2 3 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 3 nights min
                                • Child Friendly
                                • Pet Friendly
                                • Private garden

                                Price per night from

                                $104

                                Price per night from

                                $104

                                (18) Excellent 

                                  12

                                  PLATFORM 2 & 3/4, railway views, Wi-Fi, woodburner, pet-friendly with a garden

                                  North Yorkshire / Pickering

                                  Pickering house

                                  3 6 3 nights min

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

                                  Price per night from

                                  $104

                                  Price per night from

                                  $104

                                    13

                                    APPLELEAF COTTAGE, breakfast bar, open fire, exposed beams, in Pickering, Ref

                                    North Yorkshire / Pickering

                                    Pickering house

                                    2 4 3 nights min

                                    • 2 bedrooms
                                    • sleeps 4
                                    • 3 nights min
                                    • Child Friendly
                                    • Private garden

                                    Price per night from

                                    $112

                                    Price per night from

                                    $112

                                    (5) Very Good 

                                      18

                                      DAIRY HOUSE, pet-friendly, character holiday cottage, with a garden in

                                      North Yorkshire / Pickering

                                      Pickering house

                                      3 6 3 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 3 nights min
                                      • Child Friendly
                                      • Pet Friendly
                                      “A pleasant and comfortable stay.” The cottage is spacious and well appointed. It is in a peaceful location adjoining a farm. The village is a few miles from a town so a car is essential. A good venue for walking and for touring by car.

                                      Price per night from

                                      $149

                                      Price per night from

                                      $149

                                      (3) Excellent 

                                        15

                                        BECK COTTAGE, fantastic steam railway location, great touring base, character

                                        North Yorkshire / Pickering

                                        Pickering house

                                        2 4 3 nights min

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

                                        Price per night from

                                        $98

                                        Price per night from

                                        $98

                                          9

                                          LOCKTON COTTAGE, stone cottage with open fire, in Pickering, Ref 983666

                                          North Yorkshire / Pickering

                                          Pickering cottage

                                          2 4 3 nights min

                                          • 2 bedrooms
                                          • sleeps 4
                                          • 3 nights min
                                          • Child Friendly
                                          • Private garden

                                          Price per night from

                                          $143

                                          Price per night from

                                          $143

                                          (6) Excellent 

                                            21

                                            THE OLD POST OFFICE en-suites, Smart TV, WiFi in Rosedale Abbey Ref 937421

                                            Pickering / Rosedale Abbey

                                            Rosedale Abbey house

                                            5 9 3 nights min

                                            • 5 bedrooms
                                            • sleeps 9
                                            • 3 nights min
                                            • Child Friendly

                                            Price per night from

                                            $279

                                            Price per night from

                                            $279

                                              14

                                              ORCHARD COTTAGE, woodburning stove, pet friendly, near Kirbymoorside, ref 983978

                                              Pickering / Rosedale Abbey

                                              Rosedale Abbey cottage

                                              4 4 3 nights min

                                              • 4 bedrooms
                                              • sleeps 4
                                              • 3 nights min
                                              • Child Friendly
                                              • Pet Friendly
                                              • Private garden

                                              Price per night from

                                              $134

                                              Price per night from

                                              $134

                                                10

                                                ALFIE'S PLACE, pet-friendly, country holiday cottage, with a garden in

                                                North Yorkshire / Pickering

                                                Pickering house

                                                2 4 3 nights min

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

                                                Price per night from

                                                $100

                                                Price per night from

                                                $100

                                                (1) Excellent 

                                                  8

                                                  WESTGATE COTTAGE, WiFi, garden with furniture, great base for walking, Ref

                                                  North Yorkshire / Pickering

                                                  Pickering house

                                                  2 4 3 nights min

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

                                                  Price per night from

                                                  $104

                                                  Price per night from

                                                  $104

                                                  (5) Excellent 

                                                    11

                                                    KELD HEAD FARMHOUSE, detached period property, original beams, woodburner

                                                    North Yorkshire / Pickering

                                                    Pickering house

                                                    3 6 3 nights min

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

                                                    Price per night from

                                                    $182

                                                    Price per night from

                                                    $182

                                                    (13) Very Good 

                                                      14

                                                      COOPER'S COTTAGE, pet friendly, character holiday cottage, with a garden in

                                                      North Yorkshire / Pickering

                                                      Pickering house

                                                      2 4 3 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 3 nights min
                                                      • Child Friendly
                                                      • Pet Friendly
                                                      “A lovely cottage” A lovely cottage but found the stairs very dangerous to both adults and kids due to being very steep with no banister! my husband and I decided to let the kids have the double room as the other room had no door and opened onto steep

                                                      Price per night from

                                                      $104

                                                      Price per night from

                                                      $104

                                                      (4) Excellent 

                                                        19

                                                        THE OLD CARTWAY, WiFi, two sitting rooms, charming and cosy, in Pickering

                                                        North Yorkshire / Pickering

                                                        Pickering house

                                                        4 6 3 nights min

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

                                                        Price per night from

                                                        $147

                                                        Price per night from

                                                        $147

                                                        (1) Very Good 

                                                          11

                                                          CROFT COTTAGE, detached stone cottage, with WiFi and enclosed garden, in

                                                          North Yorkshire / Pickering

                                                          Pickering house

                                                          2 4 3 nights min

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

                                                          Price per night from

                                                          $107

                                                          Price per night from

                                                          $107

                                                            14

                                                            KEEP COTTAGE, enclosed garden, pet friendly, woodburning stove, Ref 904784

                                                            North Yorkshire / Pickering

                                                            Pickering house

                                                            3 5 3 nights min

                                                            • 3 bedrooms
                                                            • sleeps 5
                                                            • 3 nights min
                                                            • Child Friendly
                                                            • Pet Friendly
                                                            • Private garden

                                                            Price per night from

                                                            $134

                                                            Price per night from

                                                            $134

                                                              16

                                                              MYRTLE COTTAGE, Grade II listed, North York Moors

                                                              North Yorkshire / Pickering

                                                              Pickering cottage

                                                              2 4 3 nights min

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

                                                              Price per night from

                                                              $126

                                                              Price per night from

                                                              $126

                                                                16

                                                                POND COTTAGE, woodburning stove, pet friendly, near Kirbymoorside, Ref 983977

                                                                Pickering / Rosedale Abbey

                                                                Rosedale Abbey cottage

                                                                2 4 3 nights min

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

                                                                Price per night from

                                                                $128

                                                                Price per night from

                                                                $128

                                                                (14) Very Good 

                                                                  9

                                                                  CHERRY TREE COTTAGE, pet friendly, character holiday cottage, with open fire in

                                                                  North Yorkshire / Pickering

                                                                  Pickering house

                                                                  1 2 3 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 2
                                                                  • 3 nights min
                                                                  • Child Friendly
                                                                  • Pet Friendly
                                                                  “A lovely little retreat” Cherry tree cottage was a great little find and we will most definately be visiting again. There's everything you need within walking distance and the log burner turns the cottage into a cosy Warm retreat after a day visiting

                                                                  Price per night from

                                                                  $102

                                                                  Price per night from

                                                                  $102

                                                                  (4) Excellent 

                                                                    16

                                                                    23 ROSEDALE ABBEY, North York Moors, countryside views, WiFi

                                                                    Pickering / Rosedale Abbey

                                                                    Rosedale Abbey cottage

                                                                    3 6 3 nights min

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

                                                                    Price per night from

                                                                    $160

                                                                    Price per night from

                                                                    $160

                                                                    (8) Very Good 

                                                                      13

                                                                      HOGWARTS COTTAGE, pet-friendly, cottage with WiFi, near amenities, in

                                                                      North Yorkshire / Pickering

                                                                      Pickering house

                                                                      2 4 3 nights min

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

                                                                      Price per night from

                                                                      $107

                                                                      Price per night from

                                                                      $107

                                                                        18

                                                                        COSY COTTAGE, original features, summerhouse, centre of Pickering, Ref 963828

                                                                        North Yorkshire / Pickering

                                                                        Pickering house

                                                                        2 3 3 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 3
                                                                        • 3 nights min
                                                                        • Child Friendly
                                                                        • Private garden

                                                                        Price per night from

                                                                        $115

                                                                        Price per night from

                                                                        $115

                                                                          13

                                                                          58 WESTGATE, parking, WiFi, in Pickering

                                                                          North Yorkshire / Pickering

                                                                          Pickering cottage

                                                                          2 3 3 nights min

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

                                                                          Price per night from

                                                                          $105

                                                                          Price per night from

                                                                          $105

                                                                            22

                                                                            BRAMBLE COTTAGE, WiFi, woodburner, in Pickering

                                                                            North Yorkshire / Pickering

                                                                            Pickering cottage

                                                                            3 5 3 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 5
                                                                            • 3 nights min
                                                                            • Private garden

                                                                            Price per night from

                                                                            $156

                                                                            Price per night from

                                                                            $156

                                                                              9

                                                                              Castlegate Cottage - characterful & quaint grade II listed cottage built in 1800

                                                                              North Yorkshire / Pickering

                                                                              Pickering cottage

                                                                              3 5 2 nights min

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

                                                                              Price per night from

                                                                              $89

                                                                              Price per night from

                                                                              $89