Vacation Rentals & Cottages in Winterslow

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425 Houses

(27) Excellent 

Certificate of Excellence

    13

    Owls Lodge

    Wiltshire / Winterslow

    Winterslow lodge

    1 2 2 nights min

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

    Certificate of Excellence

    Price per night from

    $116

    Responds fast!
    avg. 1 hour 20 minutes

    Price per night from

    $116

      16

      Broomley Cottage

      Wiltshire / Winterslow

      Winterslow cottage

      1 2 2 nights min

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

      Price per night from

      $218

      Responds fast!
      avg. 1 minutes

      Price per night from

      $218

        11

        The Beadles

        Wiltshire / Winterslow

        Winterslow cottage

        1 2 3 nights min

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

        Price per night from

        $88

        Responds fast!
        avg. 1 minutes

        Price per night from

        $88

          7

          The Cottage

          Wiltshire / Winterslow

          Winterslow cottage

          2 4 2 nights min

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

          Price per night from

          $133

          Responds fast!
          avg. 1 minutes

          Price per night from

          $133

          Great rentals within 20 miles that match your search

          Distance approx 18.37 km from Winterslow

          (6) Very Good 

            8

            Old Orchard Cottage

            Wiltshire / Westbury

            Westbury cottage

            2 4 min stay varies

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

            Price per night from

            $72

            Price per night from

            $72

            Distance approx 15.63 km from Winterslow

              21

              DELUXE SHEPHERDS HUT

              Dorset / Alderholt

              Alderholt shepherds hut

              1 2 3 nights min

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

              Price per night from

              $87

              Price per night from

              $87

              Distance approx 14.75 km from Winterslow

                24

                The Arches

                Hampshire / Winchester

                Winchester cottage

                1 2 2 nights min

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

                Price per night from

                $288

                Responds fast!
                avg. 1 minutes

                Price per night from

                $288

                Distance approx 13 km from Winterslow

                  6

                  Packridge Farm (one bedroom)

                  Hampshire / Romsey

                  Romsey cottage

                  1 2 2 nights min

                  • 1 bedroom
                  • sleeps 2
                  • 2 nights min
                  • Swimming pool
                  • Pet Friendly
                  • Private garden

                  Price per night from

                  $231

                  Price per night from

                  $231

                  Distance approx 18.1 km from Winterslow

                    9

                    Grade 2 Listed Building With Great Views And Concierge

                    Hampshire / Southampton

                    Southampton apartment

                    1 2 2 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 2 nights min

                    Price per night from

                    $144

                    Price per night from

                    $144

                    Distance approx 16.32 km from Winterslow

                      55

                      Beautiful large stable building, sleeps up to 38 people, all in one huge house!

                      New Forest / Lyndhurst

                      Lyndhurst house

                      12 38 min stay varies

                      • 12 bedrooms
                      • sleeps 38
                      • min stay varies
                      • Child Friendly
                      • Pet Friendly

                      Price per night from

                      $647

                      Responds fast!
                      avg. 1 hour 52 minutes

                      Price per night from

                      $647

                      Distance approx 12.98 km from Winterslow

                      (9) Excellent 

                        15

                        Clotted Cream Apartment at Packridge

                        Hampshire / Romsey

                        Romsey cottage

                        1 4 7 nights min

                        • 1 bedroom
                        • sleeps 4
                        • 7 nights min
                        • Swimming pool
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $130

                        Price per night from

                        $130

                        Distance approx 6.15 km from Winterslow Show on Map

                          13

                          Egremont Russet

                          Stockbridge / Houghton

                          Houghton cottage

                          1 2 2 nights min

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

                          Price per night from

                          $159

                          Responds fast!
                          avg. 1 minutes

                          Price per night from

                          $159

                          Distance approx 6.73 km from Winterslow Show on Map

                          (40) Excellent 

                            30

                            Damson Cottage - The Old Barns

                            Hampshire / Stockbridge

                            Stockbridge barn

                            1 4 min stay varies

                            • 1 bedroom
                            • sleeps 4
                            • min stay varies
                            • Nearest beach 27 mi
                            • Pet Friendly

                            Price per night from

                            $195

                            Price per night from

                            $195

                            Distance approx 17.7 km from Winterslow

                            (19) Excellent 

                              19

                              Willowbank Lodges/Herons Nest

                              Wiltshire / Pewsey

                              Pewsey log cabin

                              1 2 3 nights min

                              • 1 bedroom
                              • sleeps 2
                              • 3 nights min
                              • Nearest beach 89 mi
                              • Child Friendly
                              • Pet Friendly

                              Price per night from

                              $108

                              Responds fast!
                              avg. 3 hours 34 minutes

                              Price per night from

                              $108

                              Distance approx 14.72 km from Winterslow

                                18

                                Lay Your Hat In Winchester

                                Hampshire / Winchester

                                Winchester cottage

                                1 3 2 nights min

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

                                Price per night from

                                $198

                                Responds fast!
                                avg. 1 minutes

                                Price per night from

                                $198

                                Distance approx 13.04 km from Winterslow

                                (22) Excellent 

                                Certificate of Excellence

                                  12

                                  Badgers Holt Self Catering

                                  New Forest / Fordingbridge

                                  Fordingbridge apartment

                                  1 2 2 nights min

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

                                  Certificate of Excellence

                                  Price per night from

                                  $108

                                  Responds fast!
                                  avg. 17 minutes

                                  Price per night from

                                  $108

                                  Distance approx 10.95 km from Winterslow

                                  (43) Very Good 

                                  Certificate of Excellence

                                    18

                                    Avon Vale , New Forest Self Catering Cottage for 2

                                    New Forest / Woodgreen

                                    Woodgreen cottage

                                    1 2 min stay varies

                                    • 1 bedroom
                                    • sleeps 2
                                    • min stay varies
                                    • Nearest beach 33 mi
                                    • Pet Friendly

                                    Certificate of Excellence

                                    Price per night from

                                    $70

                                    Responds fast!
                                    avg. 41 minutes

                                    Price per night from

                                    $70

                                    Distance approx 14.98 km from Winterslow

                                      10

                                      Beautiful Thatched Cottage In Village Location, With Direct Forest Access

                                      New Forest / North Gorley

                                      North Gorley house

                                      3 6 7 nights min

                                      • 3 bedrooms
                                      • sleeps 6
                                      • 7 nights min
                                      • Nearest beach 20 mi
                                      • Child Friendly
                                      • Private garden

                                      Price per night from

                                      $248

                                      Responds fast!
                                      avg. 3 hours 58 minutes

                                      Price per night from

                                      $248

                                      Distance approx 19.67 km from Winterslow

                                      (8) Excellent 

                                        20

                                        Gorse Cottage

                                        New Forest / Brockenhurst

                                        Brockenhurst cottage

                                        5 10 7 nights min

                                        • 5 bedrooms
                                        • sleeps 10
                                        • 7 nights min
                                        • Child Friendly
                                        • Pet Friendly
                                        • Private garden

                                        Price per night from

                                        $258

                                        Price per night from

                                        $258

                                        Distance approx 16.28 km from Winterslow

                                        (3) Excellent 

                                          12

                                          Delightful period cottage with the open forest and ponies on the doorstep

                                          New Forest / Lyndhurst

                                          Lyndhurst cottage

                                          3 6 min stay varies

                                          • 3 bedrooms
                                          • sleeps 6
                                          • min stay varies
                                          • Nearest beach 23 mi
                                          • Child Friendly
                                          • Private garden

                                          Price per night from

                                          $202

                                          Responds fast!
                                          avg. 1 hour 23 minutes

                                          Price per night from

                                          $202

                                          Distance approx 11.94 km from Winterslow

                                          (12) Excellent 

                                          Certificate of Excellence

                                            26

                                            Idyllic Hampshire Hideaway - The Orchard Studio, Sparsholt

                                            Hampshire / Winchester

                                            Winchester b&b

                                            1 2 1 night min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 1 night min
                                            • Child Friendly
                                            • Pet Friendly
                                            • Private garden

                                            Certificate of Excellence

                                            Price per night from

                                            $108

                                            Responds fast!
                                            avg. 3 hours 15 minutes

                                            Price per night from

                                            $108

                                            Distance approx 6.72 km from Winterslow Show on Map

                                            (6) Excellent 

                                              33

                                              The Old Barns

                                              Hampshire / Stockbridge

                                              Stockbridge barn

                                              4 8 2 nights min

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

                                              Price per night from

                                              $692

                                              Price per night from

                                              $692

                                              Distance approx 15.62 km from Winterslow

                                                8

                                                DAIRY COTTAGE

                                                Dorset / Alderholt

                                                Alderholt cottage

                                                1 3 3 nights min

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

                                                Price per night from

                                                $101

                                                Price per night from

                                                $101

                                                Distance approx 17.7 km from Winterslow

                                                (10) Excellent 

                                                  20

                                                  Willowbank Lodges

                                                  Wiltshire / Pewsey

                                                  Pewsey log cabin

                                                  8 19 min stay varies

                                                  • 8 bedrooms
                                                  • sleeps 19
                                                  • min stay varies
                                                  • Nearest beach 89 mi
                                                  • Child Friendly
                                                  • Pet Friendly

                                                  Price per night from

                                                  $658

                                                  Responds fast!
                                                  avg. 3 hours 34 minutes

                                                  Price per night from

                                                  $658

                                                  Distance approx 13.76 km from Winterslow

                                                  (11) Excellent 

                                                  Certificate of Excellence

                                                    20

                                                    Riverside Lodge

                                                    New Forest / Fordingbridge

                                                    Fordingbridge lodge

                                                    2 4 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 4
                                                    • min stay varies
                                                    • Nearest beach 15 mi
                                                    • Child Friendly
                                                    • Pet Friendly

                                                    Certificate of Excellence

                                                    Price per night from

                                                    $206

                                                    Responds fast!
                                                    avg. 1 hour 52 minutes

                                                    Price per night from

                                                    $206

                                                    Distance approx 16.55 km from Winterslow

                                                    (1) Excellent 

                                                      8

                                                      Old Manor Cottage

                                                      Wiltshire / Pewsey

                                                      Pewsey cottage

                                                      1 4 3 nights min

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

                                                      Price per night from

                                                      $116

                                                      Price per night from

                                                      $116

                                                      Distance approx 15.35 km from Winterslow

                                                        12

                                                        Bull Farm Studios - River Room

                                                        Hampshire / Kings Worthy

                                                        Kings Worthy studio

                                                        Studio 2 7 nights min

                                                        • Studio
                                                        • sleeps 2
                                                        • 7 nights min
                                                        • Private garden

                                                        Price per night from

                                                        $87

                                                        Responds fast!
                                                        avg. 2 hours 36 minutes

                                                        Price per night from

                                                        $87

                                                        Distance approx 13.27 km from Winterslow

                                                        (1) Excellent 

                                                          12

                                                          3 Bedroom, Luxury Scandinavian Lodge, set in woodland

                                                          Hampshire / Winchester

                                                          Winchester log cabin

                                                          3 6 28 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 28 nights min
                                                          • Child Friendly
                                                          • Car not necessary
                                                          • Pet Friendly

                                                          Price per night from

                                                          $139

                                                          Price per night from

                                                          $139

                                                          Distance approx 13.8 km from Winterslow

                                                          (30) Excellent 

                                                          Certificate of Excellence

                                                            76

                                                            Amble Back a short stroll from everything you need

                                                            New Forest / Fordingbridge

                                                            Fordingbridge house

                                                            2 4 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Nearest beach 26 mi
                                                            • Child Friendly
                                                            • Car not necessary

                                                            Certificate of Excellence

                                                            Price per night from

                                                            $80

                                                            Price per night from

                                                            $80

                                                            Distance approx 7.42 km from Winterslow Show on Map

                                                            (4) Excellent 

                                                              29

                                                              Meadow Cottage

                                                              Salisbury / Harnham

                                                              Harnham cottage

                                                              3 4 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 4
                                                              • min stay varies
                                                              • Nearest beach 44 mi
                                                              • Child Friendly
                                                              • Pet Friendly

                                                              Price per night from

                                                              $195

                                                              Price per night from

                                                              $195

                                                              Distance approx 14.97 km from Winterslow

                                                              (9) Excellent 

                                                                17

                                                                South House Winchester

                                                                Hampshire / Winchester

                                                                Winchester house

                                                                3 6 2 nights min

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

                                                                Price per night from

                                                                $274

                                                                Responds fast!
                                                                avg. 1 hour 32 minutes

                                                                Price per night from

                                                                $274

                                                                Distance approx 18.62 km from Winterslow

                                                                  22

                                                                  GOODREST, large garden, sleeps four, detached, Verwood, Ref 956297

                                                                  Dorset / Verwood

                                                                  Verwood house

                                                                  2 4 1 night min

                                                                  • 2 bedrooms
                                                                  • sleeps 4
                                                                  • 1 night min

                                                                  Price per night from

                                                                  $48

                                                                  Price per night from

                                                                  $48

                                                                  Distance approx 10.81 km from Winterslow

                                                                  (1) Excellent 

                                                                    6

                                                                    Large cosy house ideal for corporate lets.

                                                                    Hampshire / Andover

                                                                    Andover apartment

                                                                    3 9 1 night min

                                                                    • 3 bedrooms
                                                                    • sleeps 9
                                                                    • 1 night min
                                                                    • Child Friendly
                                                                    • Car not necessary
                                                                    • Private garden

                                                                    Price per night from

                                                                    $173

                                                                    Price per night from

                                                                    $173

                                                                    Distance approx 6.86 km from Winterslow Show on Map

                                                                    (2) Very Good 

                                                                      10

                                                                      Byways Apartments- 1 bedroom

                                                                      Wiltshire / Salisbury

                                                                      Salisbury apartment

                                                                      1 2 4 nights min

                                                                      • 1 bedroom
                                                                      • sleeps 2
                                                                      • 4 nights min

                                                                      Price per night from

                                                                      $108

                                                                      Price per night from

                                                                      $108

                                                                      Distance approx 16.19 km from Winterslow

                                                                      (152) Very Good 

                                                                        23

                                                                        Forest Lodge

                                                                        Wiltshire / New Forest National Park Wiltshire

                                                                        New Forest National Park Wiltshire log cabin

                                                                        2 4 min stay varies

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

                                                                        Price per night from

                                                                        $101

                                                                        Responds fast!
                                                                        avg. 2 hours 4 minutes

                                                                        Price per night from

                                                                        $101

                                                                        Distance approx 19.26 km from Winterslow

                                                                        (1) Excellent 

                                                                          35

                                                                          Sunnydell Cottage, New Forest Escapes

                                                                          Ringwood / Burley

                                                                          Burley house

                                                                          4 8 min stay varies

                                                                          • 4 bedrooms
                                                                          • sleeps 8
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $648

                                                                          Responds fast!
                                                                          avg. 3 hours 10 minutes

                                                                          Price per night from

                                                                          $648

                                                                          Distance approx 18.96 km from Winterslow

                                                                          (20) Excellent 

                                                                            30

                                                                            Old Bridge Cottage

                                                                            New Forest / Ringwood

                                                                            Ringwood cottage

                                                                            6 11 3 nights min

                                                                            • 6 bedrooms
                                                                            • sleeps 11
                                                                            • 3 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Nearest beach 18 mi
                                                                            • Swimming pool

                                                                            Price per night from

                                                                            $768

                                                                            Responds fast!
                                                                            avg. 1 hour 54 minutes

                                                                            Price per night from

                                                                            $768

                                                                            Distance approx 15.27 km from Winterslow

                                                                              29

                                                                              No. 01 St Swithuns Court

                                                                              Hampshire / Winchester

                                                                              Winchester townhouse

                                                                              3 6 7 nights min

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

                                                                              Price per night from

                                                                              $244

                                                                              Price per night from

                                                                              $244