Chesterfield Rentals

Close

Enter dates for more accurate prices

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

1,134 Houses

(3) Very Good 

    8

    SPRINGWELL FARM HOLIDAY COTTAGE, farmhouse, romantic, pet friendly, near

    Chesterfield / Holymoorside

    Holymoorside house

    1 2 3 nights min

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

    Price per night from

    $98

    Price per night from

    $98

    (1) Excellent 

      6

      THE BYRE, 200 year old cottage, parking, patio with furniture, in Ashover, Ref

      Chesterfield / Clay Cross

      Clay Cross house

      1 2 3 nights min

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

      Price per night from

      $93

      Price per night from

      $93

      (1) Excellent 

        16

        MANOR HOUSE, enclosed garden, WiFi, childrens play area, woodburning stove, Ref

        Chesterfield / New Tupton

        New Tupton house

        5 10 3 nights min

        • 5 bedrooms
        • sleeps 10
        • 3 nights min
        • Child Friendly
        • Private garden

        Price per night from

        $349

        Price per night from

        $349

          25

          SHIRE COTTAGE, stone barn conversion, stunning countryside views, exposed

          Chesterfield / Holestone Moor

          Holestone Moor house

          2 3 3 nights min

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

          Price per night from

          $107

          Price per night from

          $107

          (3) Very Good 

            11

            THE TACK ROOM COTTAGE, country location with charming views, character

            Chesterfield / Ashover

            Ashover house

            3 6 3 nights min

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

            Price per night from

            $175

            Price per night from

            $175

            (35) Excellent 

              11

              ACORN COTTAGE, pet friendly, character holiday cottage, with a garden in

              Chesterfield / Ashover

              Ashover house

              2 4 3 nights min

              • 2 bedrooms
              • sleeps 4
              • 3 nights min
              • Child Friendly
              • Pet Friendly
              • Private garden
              “Lovely” From the moment we arrived, we were made to feel very welcome at acorn cottage by the owners. The log burner was on, mince pies were in the oven. The cottage itself was beautiful. It was very clean and there was good information as regards

              Price per night from

              $114

              Price per night from

              $114

              (4) Excellent 

                7

                THE OLD BLACKSMITHS, beautiful stone cottage, en-suites, parking, side patio

                Chesterfield / Clay Cross

                Clay Cross house

                2 4 3 nights min

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

                Price per night from

                $105

                Price per night from

                $105

                  18

                  RUMBLINGS 1, end-terrace, king-size double, woodburner, parking, WiFi, in

                  Chesterfield / Barlow

                  Barlow house

                  2 4 3 nights min

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

                  Price per night from

                  $119

                  Price per night from

                  $119

                  (8) Excellent 

                    17

                    THE OLD STABLES, character barn conversion, en-suite, country views, in

                    Chesterfield / Ashover

                    Ashover house

                    4 8 3 nights min

                    • 4 bedrooms
                    • sleeps 8
                    • 3 nights min
                    • Child Friendly
                    • Private garden

                    Price per night from

                    $223

                    Price per night from

                    $223

                    (2) Excellent 

                      19

                      GARDENER'S COTTAGE, good touring base, flexible zip/link bed, multi-fuel stove

                      Chesterfield / Clay Cross

                      Clay Cross house

                      2 3 3 nights min

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

                      Price per night from

                      $121

                      Price per night from

                      $121

                        11

                        RUMBLINGS 3, end-terrace, woodburner, play room, parking, in Chesterfield, Ref

                        Chesterfield / Barlow

                        Barlow house

                        2 5 3 nights min

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

                        Price per night from

                        $125

                        Price per night from

                        $125

                        (1) Excellent 

                          17

                          RIBER VIEW BARN, barn conversion, views, near Ashover

                          Chesterfield / Ashover

                          Ashover cottage

                          2 4 3 nights min

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

                          Price per night from

                          $111

                          Price per night from

                          $111

                            35

                            WOODTHORPE CRUCK COTTAGE, WiFi, hot tub, near Chesterfield

                            Chesterfield / Old Tupton

                            Old Tupton cottage

                            3 6 3 nights min

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

                            Price per night from

                            $213

                            Price per night from

                            $213

                              22

                              31 RECTORY ROAD, pet-friendly, WiFi, centre of Clowne

                              Chesterfield / Clowne

                              Clowne cottage

                              2 4 3 nights min

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

                              Price per night from

                              $102

                              Price per night from

                              $102

                                10

                                THE CHAPEL, open plan living, countryside views, WIFI, converted chapel, Ref

                                Chesterfield / Ashover

                                Ashover cottage

                                1 2 3 nights min

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

                                Price per night from

                                $113

                                Price per night from

                                $113

                                (5) Excellent 

                                  9

                                  3 The Rumblings

                                  Chesterfield / Barlow

                                  Barlow cottage

                                  2 5 min stay varies

                                  • 2 bedrooms
                                  • sleeps 5
                                  • min stay varies
                                  • Child Friendly

                                  Price per night from

                                  $91

                                  Price per night from

                                  $91

                                  (5) Excellent 

                                    23

                                    Carpenters Lodge

                                    Derbyshire / Chesterfield

                                    Chesterfield lodge

                                    2 4 2 nights min

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

                                    Price per night from

                                    $132

                                    Responds fast!
                                    avg. 2 hours 26 minutes

                                    Price per night from

                                    $132

                                    (37) Excellent 

                                      20

                                      Cavendish Cottage Ashover Derbyshire

                                      Chesterfield / Ashover

                                      Ashover cottage

                                      2 4 min stay varies

                                      • 2 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Child Friendly
                                      • Pet Friendly
                                      • Private garden

                                      Price per night from

                                      $132

                                      Price per night from

                                      $132

                                      (25) Excellent 

                                      Certificate of Excellence

                                        31

                                        THE SWALLOWS

                                        Chesterfield / Cutthorpe

                                        Cutthorpe cottage

                                        3 5 3 nights min

                                        • 3 bedrooms
                                        • sleeps 5
                                        • 3 nights min
                                        • Nearest beach 100 mi
                                        • Child Friendly
                                        • Ask about pets

                                        Certificate of Excellence

                                        Price per night from

                                        $124

                                        Responds fast!
                                        avg. 1 hour 49 minutes

                                        Price per night from

                                        $124

                                        (4) Very Good 

                                          6

                                          1 The Rumblings

                                          Chesterfield / Barlow

                                          Barlow cottage

                                          2 4 min stay varies

                                          • 2 bedrooms
                                          • sleeps 4
                                          • min stay varies
                                          • Child Friendly
                                          • Pet Friendly

                                          Price per night from

                                          $88

                                          Price per night from

                                          $88

                                          (16) Excellent 

                                          Certificate of Excellence

                                            17

                                            The Barn at Woodland View

                                            Chesterfield / Barlow

                                            Barlow cottage

                                            2 4 3 nights min

                                            • 2 bedrooms
                                            • sleeps 4
                                            • 3 nights min
                                            • Child Friendly
                                            • Car not necessary
                                            • Private garden

                                            Certificate of Excellence

                                            Price per night from

                                            $103

                                            Responds fast!
                                            avg. 1 hour 52 minutes

                                            Price per night from

                                            $103

                                            (8) Excellent 

                                            Certificate of Excellence

                                              14

                                              Runner Duck Cottage

                                              Chesterfield / Cutthorpe

                                              Cutthorpe cottage

                                              1 4 2 nights min

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

                                              Certificate of Excellence

                                              Price per night from

                                              $107

                                              Responds fast!
                                              avg. 44 minutes

                                              Price per night from

                                              $107

                                              (13) Excellent 

                                                26

                                                THE ROBINS

                                                Chesterfield / Cutthorpe

                                                Cutthorpe cottage

                                                1 2 min stay varies

                                                • 1 bedroom
                                                • sleeps 2
                                                • min stay varies
                                                • Nearest beach 100 mi
                                                • Child Friendly
                                                • Pet Friendly

                                                Price per night from

                                                $95

                                                Responds fast!
                                                avg. 1 hour 49 minutes

                                                Price per night from

                                                $95

                                                (15) Excellent 

                                                Certificate of Excellence

                                                  14

                                                  Fox's Place Holiday Home

                                                  Derbyshire / Chesterfield

                                                  Chesterfield house

                                                  3 7 min stay varies

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

                                                  Certificate of Excellence

                                                  Price per night from

                                                  $161

                                                  Responds fast!
                                                  avg. 2 hours 31 minutes

                                                  Price per night from

                                                  $161

                                                  (41) Excellent 

                                                  Certificate of Excellence

                                                    17

                                                    Ippleton House (formerly Church View)

                                                    Derbyshire / Chesterfield

                                                    Chesterfield house

                                                    3 6 min stay varies

                                                    • 3 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Child Friendly
                                                    • Ask about pets
                                                    • Private garden

                                                    Certificate of Excellence

                                                    Price per night from

                                                    $103

                                                    Responds fast!
                                                    avg. 2 hours 59 minutes

                                                    Price per night from

                                                    $103

                                                    (6) Excellent 

                                                      9

                                                      2 The Rumblings

                                                      Chesterfield / Barlow

                                                      Barlow cottage

                                                      2 4 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Child Friendly

                                                      Price per night from

                                                      $88

                                                      Price per night from

                                                      $88

                                                        4

                                                        Pilsley Road

                                                        Chesterfield / Clay Cross

                                                        Clay Cross house

                                                        4 8 3 nights min

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

                                                        Price per night from

                                                        $124

                                                        Price per night from

                                                        $124

                                                        (43) Excellent 

                                                        Certificate of Excellence

                                                          19

                                                          Foxglove Cottage - Ashover near Matlock

                                                          Chesterfield / Ashover

                                                          Ashover cottage

                                                          2 4 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • min stay varies
                                                          • Child Friendly
                                                          • Pet Friendly
                                                          • Private garden

                                                          Certificate of Excellence

                                                          Price per night from

                                                          $108

                                                          Responds fast!
                                                          avg. 46 minutes

                                                          Price per night from

                                                          $108

                                                          (1) Excellent 

                                                            9

                                                            20 Holland Road

                                                            Derbyshire / Chesterfield

                                                            Chesterfield house

                                                            3 7 3 nights min

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

                                                            Price per night from

                                                            $181

                                                            Price per night from

                                                            $181

                                                            (1) Very Good 

                                                              14

                                                              Large Guest Accommodation / Holiday Let with Hottub

                                                              Chesterfield / Hardstoft

                                                              Hardstoft house

                                                              9 26 2 nights min

                                                              • 9 bedrooms
                                                              • sleeps 26
                                                              • 2 nights min
                                                              • Child Friendly
                                                              • Private garden

                                                              Price per night from

                                                              $1,022

                                                              Responds fast!
                                                              avg. 2 hours 50 minutes

                                                              Price per night from

                                                              $1,022

                                                              (23) Excellent 

                                                              Certificate of Excellence

                                                                26

                                                                The Boathouse - secluded lakeside lodge

                                                                Derbyshire / Chesterfield

                                                                Chesterfield boathouse

                                                                1 4 3 nights min

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • 3 nights min
                                                                • Beach / lakeside relaxation
                                                                • Ask about children
                                                                • Private garden

                                                                Certificate of Excellence

                                                                Price per night from

                                                                $168

                                                                Responds fast!
                                                                avg. 1 hour 51 minutes

                                                                Price per night from

                                                                $168

                                                                (46) Excellent 

                                                                  7

                                                                  Oaks Lane Farm B&B, Ashover, Derbyshire, England

                                                                  Chesterfield / Ashover

                                                                  Ashover b&b

                                                                  1 3 2 nights min

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

                                                                  Price per night from

                                                                  $117

                                                                  Responds fast!
                                                                  avg. 3 hours 27 minutes

                                                                  Price per night from

                                                                  $117

                                                                  (1) Excellent 

                                                                    11

                                                                    William Street North

                                                                    Derbyshire / Chesterfield

                                                                    Chesterfield house

                                                                    5 13 3 nights min

                                                                    • 5 bedrooms
                                                                    • sleeps 13
                                                                    • 3 nights min
                                                                    • Child Friendly
                                                                    • Ask about pets

                                                                    Price per night from

                                                                    $181

                                                                    Price per night from

                                                                    $181

                                                                    (1) Excellent 

                                                                      8

                                                                      Johnnygate Grange, Barlow Chesterfield Derbyshire, Chatsworth,Peak District,S18.

                                                                      Chesterfield / Barlow

                                                                      Barlow house

                                                                      5 10 min stay varies

                                                                      • 5 bedrooms
                                                                      • sleeps 10
                                                                      • min stay varies
                                                                      • Child Friendly
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $365

                                                                      Price per night from

                                                                      $365

                                                                      (30) Excellent 

                                                                      Certificate of Excellence

                                                                        24

                                                                        The Retreat

                                                                        Chesterfield / Ashover

                                                                        Ashover cottage

                                                                        1 2 3 nights min

                                                                        • 1 bedroom
                                                                        • sleeps 2
                                                                        • 3 nights min

                                                                        Certificate of Excellence

                                                                        Price per night from

                                                                        $117

                                                                        Responds fast!
                                                                        avg. 15 minutes

                                                                        Price per night from

                                                                        $117

                                                                        (1)  

                                                                          13

                                                                          Heywood St

                                                                          Derbyshire / Chesterfield

                                                                          Chesterfield house

                                                                          3 6 2 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 2 nights min
                                                                          • Child Friendly
                                                                          • Car not necessary
                                                                          • Ask about pets

                                                                          Price per night from

                                                                          $135

                                                                          Price per night from

                                                                          $135

                                                                          (1) Excellent 

                                                                            14

                                                                            72 Holland Road

                                                                            Derbyshire / Chesterfield

                                                                            Chesterfield house

                                                                            3 8 2 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 8
                                                                            • 2 nights min
                                                                            • Child Friendly
                                                                            • Private garden

                                                                            Price per night from

                                                                            $139

                                                                            Price per night from

                                                                            $139

                                                                            (45) Excellent 

                                                                            Certificate of Excellence

                                                                              21

                                                                              Columbine Cottage - Ashover holiday rental

                                                                              Chesterfield / Ashover

                                                                              Ashover cottage

                                                                              3 6 min stay varies

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

                                                                              Certificate of Excellence

                                                                              Price per night from

                                                                              $132

                                                                              Responds fast!
                                                                              avg. 46 minutes

                                                                              Price per night from

                                                                              $132