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The best holiday rentals in Winchester

Check out our pick of great holiday rentals in Winchester

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Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

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City Apartment is located in Winchester, 20 km from Southampton Guildhall, 22 km from Southampton Cruise Terminal, and 25 km from Ageas Bowl. Featuring inner courtyard and quiet street views, this apartment also has free WiFi. The property is non-smoking and is set 20 km from The Mayflower Theatre.

Everything was perfect and we hope to stay again on our next visit to the UK. The apartment was very clean and comfortable, very nicely decorated and furnished. I prefer this kind of place to stay above people's homes which are full of personal belongings. Couldn't ask for a better place to stay - we loved it.

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9.5
Exceptional
121 reviews
Price from
721 zł
per night

Offering free WiFi, Esme's offers accommodation in Winchester, within walking distance from Wolvesey Castle and 550 metres from the Winchester Cathedral.

The room comes with a flat-screen TV<,a shower room and a hair dryer.

Warm, welcoming and very comfortable.

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9.6
Exceptional
106 reviews
Price from
776 zł
per night

Set in Winchester, 16 km from The Mayflower Theatre and 16 km from Southampton Guildhall, Idyllic Studio Flat offers air-conditioned accommodation with a terrace and free WiFi. With garden views, this accommodation features a patio. The property is non-smoking and is situated 17 km from Southampton Cruise Terminal.

Beautiful neighborhood with gorgeous greenery and landscaping. Gorgeous views, closes to multiple footpaths, convient location for access to nice pubs, sites and Winchester. The studio flat was modern and thoughtfully designed, and stocked with quality items for a comfortable stay.

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9.1
Superb
100 reviews
Price from
425 zł
per night

The Fox is located in Crawley, 7 km from Winchester. Free parking is available on site.

All rooms are en-suite and feature free WiFi, Egyptian cotton sheets, a flat-screen TV and coffee & tea making facilities.

Very helpful staff, delicious food - both dinner and breakfast

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9.6
Exceptional
413 reviews
Price from
596 zł
per night

Two Bare Feet is located in Winchester, within a 10-minute walk from the train station. The accommodation offers suites with a shared kitchen. There is free WiFi throughout.

The suites at Two Bare Feet are individually designed, and each has an en suite with either a bath or shower. The rooms have a TV, sofa and desk.

The instructions provided by the host were excellent, and I had no difficulties in locating the buidling--even though it is tucked off the street up a driveway--or in getting into my room. The tranquility and quiet were very welcome. Very comfortable bed, nice big shower, useful work desk, plenty of storage space. Very nice shared kitchen facilities! Within a few blocks of a wide selection of cafés, restaurants, and other stores.

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9.3
Superb
422 reviews
Price from
532 zł
per night

The spacious holiday home is fitted with 4 bedrooms, 2 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a terrace with garden views. For added privacy, the accommodation features a private entrance.

Very clean and tidy. Clear instructions for entry. Came back to me quickly when I had a query.

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9.2
Superb
13 reviews
Price from
1,791 zł
per night

This holiday home has 3 bedrooms, a kitchen with an oven and a toaster, a flat-screen TV, a seating area and 1 bathroom fitted with a bath. Towels and bed linen are offered in the holiday home. The property has an outdoor dining area.

Spacious home. Perfect location. Quiet.

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9.4
Superb
43 reviews
Price from
1,021 zł
per night

Situated in Winchester in the Hampshire region, Jubilee apartment, Winchester has a terrace and inner courtyard views. This apartment features accommodation with a patio. Free WiFi is available throughout the property and The Mayflower Theatre is 22 km away.

Clean, dry and warm, centrally located, close to station, theatre and cafes.

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9.7
Exceptional
15 reviews
Price from
876 zł
per night

Situated in Winchester and only 19 km from The Mayflower Theatre, 4 Bed City House with Private Garden and Parking features accommodation with garden views, free WiFi and free private parking. The property features city and inner courtyard views, and is 20 km from Southampton Guildhall. Outdoor dining is also possible at the holiday home.

Lovely property, very well maintained.

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9.6
Exceptional
27 reviews
Price from
1,485 zł
per night

The spacious holiday home comes with 3 bedrooms, a flat-screen TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are provided in the holiday home. The property has an outdoor dining area.

The location was fabulous. Easy to get to the centre of things.

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9.2
Superb
26 reviews
Price from
1,066 zł
per night

Most booked holiday rentals in Winchester this month

Enjoy breakfast in Winchester!

  • City Apartment
    Breakfast options
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 121 reviews

    City Apartment is located in Winchester, 20 km from Southampton Guildhall, 22 km from Southampton Cruise Terminal, and 25 km from Ageas Bowl.

    The owners were super helpful and staying up late to guide us to the key lock box.

  • Esme's
    Breakfast options
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 106 reviews

    Offering free WiFi, Esme's offers accommodation in Winchester, within walking distance from Wolvesey Castle and 550 metres from the Winchester Cathedral.

    Breakfast was not included. The welcome was great.

  • Idyllic Studio Flat
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 100 reviews

    Set in Winchester, 16 km from The Mayflower Theatre and 16 km from Southampton Guildhall, Idyllic Studio Flat offers air-conditioned accommodation with a terrace and free WiFi.

    The accommodation is very stylish and modern. Bed was extremely comfortable.

  • The Fox
    Breakfast options
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 413 reviews

    The Fox is located in Crawley, 7 km from Winchester. Free parking is available on site.

    Property was immaculately clean with locally sourced products

  • Two Bare Feet
    Breakfast options
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 422 reviews

    Two Bare Feet is located in Winchester, within a 10-minute walk from the train station. The accommodation offers suites with a shared kitchen. There is free WiFi throughout.

    It was very clean very spacious and done to a high standard

  • Family home in Hampshire - Sleeps up to 9 people with 3 parking spaces
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 13 reviews

    Family home in Hampshire - Sleeps up to 9 people with 3 parking spaces, a property with a garden, is situated in Winchester, 21 km from Southampton Guildhall, 22 km from Southampton Cruise Terminal,...

    It had the space we needed and was very well presented.

  • Millstream House
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 43 reviews

    Boasting river views, Millstream House features accommodation with a garden and a patio, around 21 km from The Mayflower Theatre.

    The property was beautiful in a beautiful location.

  • Jubilee apartment, Winchester
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 15 reviews

    Situated in Winchester in the Hampshire region, Jubilee apartment, Winchester has a terrace and inner courtyard views. This apartment features accommodation with a patio.

    Great location, well decorated, all new and clean. Host is very kind .

These holiday rentals in Winchester have options with FREE cancellation

  • Bell tent glamping at Marwell Resort
    Free cancellation options available
    7.8
    Scored 7.8
    Good
    Rated good
     · 134 reviews

    Offering a garden and garden view, Bell tent glamping at Marwell Resort is set in Winchester, 10 km from Ageas Bowl and 17 km from Southampton Guildhall.

    Staff was fantastic and enjoyed staying in the bell tents

  • 61
    Free cancellation options available
    7.5
    Scored 7.5
    Good
    Rated good
     · 257 reviews

    61 in Winchester offers accommodation with free WiFi, 19 km from The Mayflower Theatre, 19 km from Southampton Guildhall and 20 km from Southampton Cruise Terminal.

    Very helpful owner I'd definitely stay there again 😇💯

  • 4 Bed City House with Private Garden and Parking
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 27 reviews

    Situated in Winchester and only 19 km from The Mayflower Theatre, 4 Bed City House with Private Garden and Parking features accommodation with garden views, free WiFi and free private parking.

    Great location. Close to the high street. Lovely property.

  • House situated on River Itchen
    Free cancellation options available
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 26 reviews

    Offering a garden and city view, House situated on River Itchen is located in Winchester, 22 km from Southampton Cruise Terminal and 25 km from Ageas Bowl.

    Fantastic property, very modern and fab location over looking the river.

  • Beautiful house on the River Itchen
    Free cancellation options available
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 26 reviews

    Situated in Winchester, 21 km from The Mayflower Theatre and 21 km from Southampton Guildhall, Beautiful house on the River Itchen features accommodation with free WiFi in a historic building.

    Lovely clean house with everything you need. Excellent location.

  • Sky View
    Free cancellation options available
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 37 reviews

    Set 21 km from Southampton Guildhall, 23 km from Southampton Cruise Terminal and 26 km from Ageas Bowl, Sky View provides accommodation located in Winchester.

    Amazing spacious place! Very clean and easy check in.

  • No2 St Peters Street
    Free cancellation options available
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 8 reviews

    Providing a garden, a bar and free WiFi, No2 St Peters Street is a recently renovated holiday home 20 km from The Mayflower Theatre and 20 km from Southampton Guildhall.

    The decor was beautiful and done to a really high standard. Everything was spotless and the location was perfect!

  • The Barrel Room at The Northbrook Arms
    Free cancellation options available
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 56 reviews

    Set in Winchester, within 23 km of Jane Austen's House Museum and 29 km of Highclere Castle, The Barrel Room at The Northbrook Arms offers accommodation with a bar as well as free private parking for...

    Gorgeous room, well equipped and very comfortable.

Highly rated holiday rentals in Winchester

  • The Nestle House
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 12 reviews

    Located in Winchester, The Nestle House is a historic holiday home that provides free WiFi, and guests can enjoy a garden and a terrace. With city views, this accommodation offers a patio.

    The attention to detail was exceptional from the host.

  • Boscobel Apartments Down
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 20 reviews

    Boscobel Apartments Down, a property with a garden, is set in Winchester, 21 km from Southampton Guildhall, 23 km from Southampton Cruise Terminal, as well as 26 km from Ageas Bowl.

    Location was excellent - everything you could need in this comfy little apartment

  • Boscobel Apartments Up
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 54 reviews

    Boscobel Apartments Up is set in Winchester, 21 km from Southampton Guildhall, 23 km from Southampton Cruise Terminal, and 26 km from Ageas Bowl.

    The environment is great and the landlord is very patient:)

  • Jabba, The Hut
    8.0+ review score
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 79 reviews

    Jabba, The Hut, a property with a garden, is situated in Winchester, 25 km from The Mayflower Theatre, 25 km from Southampton Guildhall, as well as 27 km from Southampton Cruise Terminal.

    Great time at jabba the hut, will definitely be back.

  • Mallard Cottage
    8.0+ review score
    9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 9 reviews

    Mallard Cottage, a property with a garden, is situated in Winchester, 25 km from Ageas Bowl, 26 km from Jane Austen's House Museum, as well as 34 km from Highclere Castle.

    The location was great, and off road parking was invaluable. The owners were very welcoming.

  • Walsingham House - Peaceful Elevated - Near Oram's Arbour
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 29 reviews

    Featuring garden views, Walsingham House - Peaceful Elevated - Near Oram's Arbour provides accommodation with a garden and a terrace, around 21 km from The Mayflower Theatre.

    It’s a wow property. Super clean. With all facilities

  • Gorgeous Apartment in the centre of Winchester
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 5 reviews

    Set in Winchester and only 22 km from The Mayflower Theatre, Gorgeous Apartment in the centre of Winchester offers accommodation with quiet street views, free WiFi and free private parking.

    Well situated. Everything provided, e.g. towels, sheets, toilet rolls, dishwasher capsules. Really helpful not to have to immediately go out shopping. Warm, clean and comfortable.

  • No 3 Old Printworks
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 23 reviews

    Set in Winchester in the Hampshire region, No 3 Old Printworks offers accommodation with free WiFi and free private parking.

    Location was very central and perfect for exploring Winchester

FAQ about holiday rentals in Winchester







Holiday rentals that guests love in Winchester

  • Avg. price/night: 615.62 zł
    7.9
    Scored 7.9
    Good
    Rated good
     · 623 reviews
    Loved to village feel.
    Williams
    Family with young children
  • Avg. price/night: 615.62 zł
    7.9
    Scored 7.9
    Good
    Rated good
     · 623 reviews
    Nice place in a small village. Stayed there to be a bit closer to the ferry in Southhampton. The kitchen had already closed by the time we got there, but we found something nearby. Just a 7 min drive.
    M
    Michael
    Young couple
  • Avg. price/night: 700.71 zł
    9.4
    Scored 9.4
    Superb
    Rated superb
     · 11 reviews
    The room - we had a family one was really well set up - it was an L shaped room and was great for a family. The host was wonderful and really made our stay. There was lovely touches with fresh milk and a tiny fridge for it, breakfast was delicious and we also had an evening meal in the pub which was great and there was a really lovely atmosphere - proper village pub. Would recommend a stay here and will look to stay here again.
    Vicki
    Family with young children
  • Avg. price/night: 550.56 zł
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 926 reviews
    A luxurious room in an ancient pub - and wow the food! Loved every moment of the stay with friendly staff and surrounded by pictures on the walls depicting the pub's ancient past. Comfy bed, peaceful night (it is in a rural village after all). Lovely walks around the area. Plenty of room in the car park.
    Nick
    Young couple
  • Avg. price/night: 795.80 zł
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 413 reviews
    The venue was absolutely gorgeous, a stunning little village, the staff were all very friendly and gave wonderful advice on places to visit. The morning breakfast was fantastic, much more than expected!
    Danielle
    Young couple
  • Avg. price/night: 615.62 zł
    7.9
    Scored 7.9
    Good
    Rated good
     · 623 reviews
    The location was great, in a nice quiet village not too far from work and only a 3 minute walk to a lovely restaurant which we had been to before. The decor was nicely done and continued it's theme throughout.
    Tracy
    Young couple
  • Avg. price/night: 530.54 zł
    8.5
    Scored 8.5
    Very good
    Rated very good
     · 1,319 reviews
    Quirky and friendly. Staff were kind and accommodating, nothing was too much trouble. Dietary needs catered for. Food excellent and plentiful. Lovely comfortable (stable) room. Immaculately clean. Loved the interior of the main building which used repurposed furniture and horse related items in an imaginative way. Great village location but close enough to Winchester City for exploring.
    Karen
    Young couple
  • Avg. price/night: 795.80 zł
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 413 reviews
    Beautiful village Exceptional building Spotlessly clean Excellent food and choice Staff outstanding Recommend anyone to stay here
    william
    Young couple
  • 9.9
    Scored 9.9
    Exceptional
    Rated exceptional
     · 9 reviews
    I have stay in a lot of holiday homes and one was by far the best. High spec and accommodating hosts.
    Brian
    People with friends
  • 9.0
    Scored 9.0
    Superb
    Rated superb
     · 4 reviews
    Everything was wonderful. Feels like home, it was very clean and comfortable. Additionally the landlady was too sweet and caring. This holiday home is surely one of the best place to stay in Winchester. Will miss this place alot as it was such a beautiful place to stay. Thank you Miss.Lund for everything during our stay :)
    Evanglin
    Solo traveller

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