Vacation Rentals & Cottages in Winchester

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362 Houses

(4) Excellent 

    21

    South House - In the centre of Winchester

    Hampshire / Winchester

    Winchester house

    3 6 2 nights min

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

    Price per night from

    $273

    Responds fast!
    avg. 25 minutes

    Price per night from

    $273

    (39) Excellent 

    Certificate of Excellence

      19

      Hang Your Hat - classy hideaway in Winchester

      Hampshire / Winchester

      Winchester cottage

      1 3 2 nights min

      • 1 bedroom
      • sleeps 3
      • 2 nights min
      • Car not necessary
      • Private garden
      “A perfect 3 night break in every way!” We recently stayed at 'Hang Your Hat' for 3 nights and wished we could have stayed longer. As soon as we saw the cottage we loved it! It had everything you would want from a holiday home and more. We brought our

      Certificate of Excellence

      Price per night from

      $208

      Responds fast!
      avg. 1 hour 10 minutes

      Price per night from

      $208

      (13) Very Good 

      Certificate of Excellence

        11

        HARDY HOUSE, WINCHESTER

        Hampshire / Winchester

        Winchester b&b

        1 2 1 night min

        • 1 bedroom
        • sleeps 2
        • 1 night min
        • Nearest beach 45 mi
        • Car not necessary
        • Air conditioning
        “Relaxed modern home experience” We had such a good stay here when we stumbled on it, shortly after it opened, that we came back to stay a second time. Although the room is small it is very light and modern and very comfortable. The shower room has eve

        Certificate of Excellence

        Price per night from

        $115

        Price per night from

        $115

          4

          Exec Spec Apartments

          Hampshire / Winchester

          Winchester apartment

          1 4 1 night min

          • 1 bedroom
          • sleeps 4
          • 1 night min
          • Child Friendly

          Price per night from

          $215

          Price per night from

          $215

            17

            Winchester Cottage Opposite Famous Organic FarmShop - 3 Bedrooms & Garden Office

            Hampshire / Winchester

            Winchester house

            3 5 3 nights min

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

            Price per night from

            $169

            Price per night from

            $169

            (2) Very Good 

              7

              Sunnyside

              Hampshire / Winchester

              Winchester apartment

              1 2 2 nights min

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

              Price per night from

              $129

              Responds fast!
              avg. 56 minutes

              Price per night from

              $129

                12

                43193 Cottage situated in Winchester

                Hampshire / Winchester

                Winchester house

                2 3 7 nights min

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

                Price per night from

                $99

                Price per night from

                $99

                (13) Excellent 

                Certificate of Excellence

                  22

                  The Hayloft, Crabwood Cottages

                  Hampshire / Winchester

                  Winchester guest house

                  1 2 1 night min

                  • 1 bedroom
                  • sleeps 2
                  • 1 night min
                  • Nearest beach 25 mi
                  • Pet Friendly

                  Certificate of Excellence

                  Price per night from

                  $122

                  Responds fast!
                  avg. 2 hours 9 minutes

                  Price per night from

                  $122

                  (6) Very Good 

                    41

                    Willow Cottage - The Old Barns

                    Hampshire / Winchester

                    Winchester barn

                    1 2 min stay varies

                    • 1 bedroom
                    • sleeps 2
                    • min stay varies
                    • Pet Friendly

                    Price per night from

                    $180

                    Price per night from

                    $180

                    (9) Excellent 

                    Certificate of Excellence

                      15

                      Charming apartment, 1 bed, easy walk to Cathedral and restaurants, lovely views

                      Hampshire / Winchester

                      Winchester apartment

                      1 2 2 nights min

                      • 1 bedroom
                      • sleeps 2
                      • 2 nights min
                      • Car not necessary

                      Certificate of Excellence

                      Price per night from

                      $129

                      Responds fast!
                      avg. 1 hour 35 minutes

                      Price per night from

                      $129

                      (4) Excellent 

                        20

                        Luxury 3 Bedroom, Scandinavian Lodge with HOT TUB

                        Hampshire / Winchester

                        Winchester lodge

                        3 6 min stay varies

                        • 3 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $205

                        Price per night from

                        $205

                        (8) Very Good 

                          11

                          The Loft Winchester

                          Hampshire / Winchester

                          Winchester apartment

                          3 5 2 nights min

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

                          Price per night from

                          $223

                          Price per night from

                          $223

                          (18) Very Good 

                            22

                            City Centre Apartment Winchester

                            Hampshire / Winchester

                            Winchester apartment

                            1 4 5 nights min

                            • 1 bedroom
                            • sleeps 4
                            • 5 nights min
                            • Child Friendly
                            • Car not necessary

                            Price per night from

                            $158

                            Price per night from

                            $158

                            (12) Very Good 

                            Certificate of Excellence

                              14

                              The Granary Annex at Worthy Barn

                              Hampshire / Winchester

                              Winchester house

                              2 4 2 nights min

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

                              Certificate of Excellence

                              Price per night from

                              $147

                              Price per night from

                              $147

                              (9) Excellent 

                                17

                                Stylish House in Winchester

                                Hampshire / Winchester

                                Winchester house

                                2 6 5 nights min

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

                                Price per night from

                                $251

                                Price per night from

                                $251

                                (3) Excellent 

                                  21

                                  Luxury 2 Bedroom Scandinavian Lodge with HOT TUB

                                  Hampshire / Winchester

                                  Winchester lodge

                                  2 4 min stay varies

                                  • 2 bedrooms
                                  • sleeps 4
                                  • min stay varies
                                  • Nearest beach 20 mi
                                  • Child Friendly
                                  • Pet Friendly

                                  Price per night from

                                  $177

                                  Price per night from

                                  $177

                                    7

                                    Family home in beautiful Hampshire countryside

                                    Hampshire / Winchester

                                    Winchester house

                                    5 10 2 nights min

                                    • 5 bedrooms
                                    • sleeps 10
                                    • 2 nights min
                                    • Swimming pool
                                    • Child Friendly
                                    • Pet Friendly

                                    Price per night from

                                    $1,147

                                    Responds fast!
                                    avg. 3 hours 27 minutes

                                    Price per night from

                                    $1,147

                                    (10) Very Good 

                                      18

                                      Cosy character cottage in central Winchester

                                      Hampshire / Winchester

                                      Winchester cottage

                                      2 4 min stay varies

                                      • 2 bedrooms
                                      • sleeps 4
                                      • min stay varies
                                      • Child Friendly
                                      • Car not necessary
                                      • Private garden

                                      Price per night from

                                      $215

                                      Price per night from

                                      $215

                                      (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

                                        (21) Excellent 

                                        Certificate of Excellence

                                          31

                                          The Old Tractor Barn, Crabwood Cottages

                                          Winchester / Pitt

                                          Winchester cottage

                                          3 5 min stay varies

                                          • 3 bedrooms
                                          • sleeps 5
                                          • min stay varies
                                          • Nearest beach 30 mi
                                          • Child Friendly
                                          • Pet Friendly

                                          Certificate of Excellence

                                          Price per night from

                                          $125

                                          Responds fast!
                                          avg. 2 hours 9 minutes

                                          Price per night from

                                          $125

                                          (10) Excellent 

                                            15

                                            The Down House Cottage

                                            Hampshire / Winchester

                                            Winchester cottage

                                            1 2 3 nights min

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

                                            Price per night from

                                            $129

                                            Price per night from

                                            $129

                                              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

                                              $243

                                              Price per night from

                                              $243

                                              (11) Excellent 

                                                20

                                                Luxury 3 bedroom Scandinavian Lodge

                                                Hampshire / Winchester

                                                Winchester log cabin

                                                3 6 min stay varies

                                                • 3 bedrooms
                                                • sleeps 6
                                                • min stay varies
                                                • Nearest beach 20 mi
                                                • Child Friendly
                                                • Pet Friendly

                                                Price per night from

                                                $177

                                                Price per night from

                                                $177

                                                (22) Excellent 

                                                  15

                                                  The Sky Penthouse

                                                  Hampshire / Winchester

                                                  Winchester penthouse

                                                  2 6 2 nights min

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

                                                  Price per night from

                                                  $280

                                                  Responds fast!
                                                  avg. 2 hours 0 minutes

                                                  Price per night from

                                                  $280

                                                  (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

                                                    $273

                                                    Responds fast!
                                                    avg. 1 hour 32 minutes

                                                    Price per night from

                                                    $273

                                                    (8) Excellent 

                                                      13

                                                      Luxury 2 Bedroom Scandinavian Lodge

                                                      Hampshire / Winchester

                                                      Winchester log cabin

                                                      2 4 min stay varies

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • min stay varies
                                                      • Nearest beach 20 mi
                                                      • Child Friendly
                                                      • Pet Friendly

                                                      Price per night from

                                                      $208

                                                      Price per night from

                                                      $208

                                                        17

                                                        No. 01b 1 Clifton Terrace

                                                        Hampshire / Winchester

                                                        Winchester apartment

                                                        1 3 7 nights min

                                                        • 1 bedroom
                                                        • sleeps 3
                                                        • 7 nights min
                                                        • Child Friendly
                                                        • Car not necessary

                                                        Price per night from

                                                        $274

                                                        Price per night from

                                                        $274

                                                          47

                                                          No. 11 Cossack Lane House

                                                          Hampshire / Winchester

                                                          Winchester apartment

                                                          2 4 7 nights min

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • 7 nights min
                                                          • Ask about children

                                                          Price per night from

                                                          $177

                                                          Price per night from

                                                          $177

                                                            11

                                                            No. 79 Tower Street

                                                            Hampshire / Winchester

                                                            Winchester house

                                                            2 7 7 nights min

                                                            • 2 bedrooms
                                                            • sleeps 7
                                                            • 7 nights min
                                                            • Child Friendly

                                                            Price per night from

                                                            $267

                                                            Price per night from

                                                            $267

                                                              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

                                                              $287

                                                              Responds fast!
                                                              avg. 1 minutes

                                                              Price per night from

                                                              $287

                                                                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

                                                                $197

                                                                Responds fast!
                                                                avg. 1 minutes

                                                                Price per night from

                                                                $197

                                                                  25

                                                                  The Loft at St Thomas'

                                                                  Hampshire / Winchester

                                                                  Winchester cottage

                                                                  2 4 2 nights min

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

                                                                  Price per night from

                                                                  $323

                                                                  Responds fast!
                                                                  avg. 1 minutes

                                                                  Price per night from

                                                                  $323

                                                                    13

                                                                    Panoramic view of Winchester Cathedral

                                                                    Hampshire / Winchester

                                                                    Winchester apartment

                                                                    1 2 3 nights min

                                                                    • 1 bedroom
                                                                    • sleeps 2
                                                                    • 3 nights min
                                                                    • Nearest beach 40 mi
                                                                    • Car not necessary

                                                                    Price per night from

                                                                    $180

                                                                    Price per night from

                                                                    $180

                                                                      15

                                                                      Dashwood Terrace

                                                                      Hampshire / Winchester

                                                                      Winchester cottage

                                                                      2 5 2 nights min

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

                                                                      Price per night from

                                                                      $151

                                                                      Responds fast!
                                                                      avg. 1 minutes

                                                                      Price per night from

                                                                      $151

                                                                        15

                                                                        City Centre Home With Private Off Road Parking

                                                                        Hampshire / Winchester

                                                                        Winchester house

                                                                        2 4 2 nights min

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

                                                                        Price per night from

                                                                        $172

                                                                        Responds fast!
                                                                        avg. 43 minutes

                                                                        Price per night from

                                                                        $172

                                                                        (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

                                                                          $138

                                                                          Price per night from

                                                                          $138

                                                                            14

                                                                            2 Bedroom, Luxury Scandinavian Lodge set in woodland

                                                                            Hampshire / Winchester

                                                                            Winchester log cabin

                                                                            2 4 28 nights min

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

                                                                            Price per night from

                                                                            $124

                                                                            Price per night from

                                                                            $124

                                                                            Great rentals within 20 miles that match your search

                                                                            Distance approx 8.47 km from Winchester

                                                                            (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

                                                                              $194

                                                                              Price per night from

                                                                              $194

                                                                              Why Winchester?

                                                                              Based in the county of Hampshire, England, Winchester is a city steeped in history. With cultural landmarks, family attractions and more, book your vacation rental in Winchester today and enjoy an action-packed trip to this beautiful city.

                                                                              About Winchester

                                                                              Winchester has been the setting for many novels, including The Whole Day Through by Patrick Gale and One Day by David Nicholls.

                                                                              What to Do

                                                                              Winchester Science Centre and Planetarium has over 100 exhibitions where you can discover more about the universe. You can also find out more about the human body as well as live shows and workshops.

                                                                              Top Winchester Travel Tips

                                                                              Take a visit to the stunning city of Winchester and marvel at the exquisite range of attractions on offer. Book your vacation rental in Winchester today to enjoy one of the best historic and cultural cities within the UK.