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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.

It was very clean, well equipped, lots of nice extras like milk, cereals, wine and tea. That was a nice surprise and great location.

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9.5
Exceptional
125 reviews
Price from
£146.25
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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9.2
Superb
103 reviews
Price from
£84.92
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.

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!

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9.6
Exceptional
422 reviews
Price from
£159
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
420 reviews
Price from
£106.25
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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9.3
Superb
51 reviews
Price from
£203.90
per night

Located in Winchester in the Hampshire region, No 2 The Old School House, Winchester provides accommodation with free WiFi and free private parking. The property is situated 22 km from Southampton Guildhall, 23 km from Southampton Cruise Terminal and 26 km from Jane Austen's House Museum. The property is non-smoking and is set 22 km from The Mayflower Theatre.

Great appartment and location. Claire was great to deal with. We stayed here twice on our trip to the Uk. Cameron NZ

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9.7
Exceptional
6 reviews
Price from
£251.33
per night

Boasting city views, The Penthouse, Winchester features accommodation with a terrace, around 21 km from The Mayflower Theatre. Among the facilities at this property are a lift and private check-in and check-out, along with free WiFi throughout the property. The property is non-smoking and is situated 21 km from Southampton Guildhall.

A very spacious and well cleaned flat right at the Westgate with three comfortable bedrooms and a huge living room/kitchen. We didn't spend a lot of time in the space itself but it has everything you could ask for and even enough space in the living room for a quick group round of video games on the TV. (Yes, we're the kind of people who travel with a console.) One bedroom has an en suite with a shower, the other bathroom is shared between two bedrooms and that's the one that comes with a tub. There were even complimentary coffee pods and milk, there's nothing else we could have asked for. If I happen to be in the area again I'll for sure look for availability here.

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9.8
Exceptional
5 reviews
Price from
£250
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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9.5
Exceptional
29 reviews
Price from
£313.80
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
28 reviews
Price from
£213
per night

The spacious holiday home features 3 bedrooms, 3 bathrooms, bed linen, towels, a flat-screen TV with streaming services, a dining area, a fully equipped kitchen, and a patio with river views. A private entrance leads guests into the holiday home, where they can enjoy some chocolates or cookies. The property has an outdoor dining area.

Prompt response when I requested access codes on the day of arrival. Washing machine for laundry.

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9.1
Superb
29 reviews
Price from
£213
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
     · 125 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.

  • Idyllic Studio Flat
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 103 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
     · 422 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
     · 420 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.

    A fantastically presented property in an excellent location.

  • Millstream House
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 51 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.

  • No 2 The Old School House, Winchester
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 6 reviews

    Located in Winchester in the Hampshire region, No 2 The Old School House, Winchester provides accommodation with free WiFi and free private parking.

    Location very central but in a quiet street Accommodation was spacious and comfortable Parking space was essential!

  • The Penthouse, Winchester
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 5 reviews

    Boasting city views, The Penthouse, Winchester features accommodation with a terrace, around 21 km from The Mayflower Theatre.

    Very clean and spacious in an excellent position.

  • 4 Bed City House with Private Garden and Parking
    9.5
    Scored 9.5
    Exceptional
    Rated exceptional
     · 29 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.

These holiday rentals in Winchester have options with FREE cancellation

  • House situated on River Itchen
    Free cancellation options available
    9.2
    Scored 9.2
    Superb
    Rated superb
     · 28 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
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 29 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
     · 38 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
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 61 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.

  • The Nestle House
    Free cancellation options available
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 14 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
    Free cancellation options available
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 22 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
    Free cancellation options available
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 55 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:)

Highly rated holiday rentals in Winchester

  • Jabba, The Hut
    8.0+ review score
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 82 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

    Set in Winchester in the Hampshire region, Mallard Cottage offers accommodation with free WiFi and free private parking.

    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

  • Esme's
    8.0+ review score
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 99 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.

  • Gorgeous Apartment in the centre of Winchester
    9.1
    Scored 9.1
    Superb
    Rated superb
     · 7 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.

    Location, very comfy beds, nice touch ro leave milk &crossiants

  • 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

  • The Sky Penthouse
    9.8
    Scored 9.8
    Exceptional
    Rated exceptional
     · 42 reviews

    Set in Winchester, in a historic building, 22 km from The Mayflower Theatre, The Sky Penthouse is an apartment with a fitness centre and massage services.

    物业位于城市核心地段,靠温切斯特大教堂不远,车行5分钟可以抵达。房间非常干净有艺术感。房东太太非常nice。家里整洁而舒适。值得推荐

  • Hang Your Hat
    8.0+ review score
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 97 reviews

    Set in a former Brewery workers cottage built by Lord Northbrook in 1843, Hang Your Hat is situated in Winchester and offers accommodation with a private courtyard garden, free WiFi and a log...

    Home from home .Christmas tree was a lovely touch Would definitely recommend

FAQ about holiday rentals in Winchester







Holiday rentals that guests love in Winchester

  • Avg. price/night: £159
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 422 reviews
    A beautiful pub in a lovely village location. Breakfast was excellent with generous portions
    Neil
    Young couple
  • Avg. price/night: £140
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 860 reviews
    It’s nice and central in a lovely village Rooms were comfortable and everything you needed was there. Breakfast was very good. Staff were very friendly
    Gabriele
    Family with young children
  • 8.8
    Scored 8.8
    Fabulous
    Rated fabulous
     · 95 reviews
    Location was convenient for Winchester and beautiful, with lots of different animals in the fields nearby. Beds were comfortable. We made a mistake in the booking and checked in a day early(!) but the host was very accommodating and sorted it out for us. Also my husband currently has a health condition that means he gets cold easily--hosts kindly remotely jacked up the thermostat and husband was warm and comfortable. Everything you could want is provided in the property and unlike most such holiday rentals, the house is spacious.
    Claire
    Young couple
  • Avg. price/night: £159
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 422 reviews
    We liked everything about it. beautiful room, size of bed, bath, fridge in room, plentiful tea, coffee, biscuits and fresh milk, excellent breakfast, nice meal in the evening, nice and quiet, parking, staff, great location and interesting village
    I
    Ian
    Young couple
  • Avg. price/night: £121
    7.9
    Scored 7.9
    Good
    Rated good
     · 633 reviews
    Loved to village feel.
    Williams
    Family with young children
  • Avg. price/night: £121
    7.9
    Scored 7.9
    Good
    Rated good
     · 633 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: £120
    8.9
    Scored 8.9
    Fabulous
    Rated fabulous
     · 21 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: £121
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 933 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
  • 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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