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The best holiday rentals in Winchester

Check out our pick of great holiday rentals in Winchester

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Two Bare Feet, hotel in Winchester

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 really lucky for us to choose ‘two bare feet’! A few minutes walk from high street. We liked our room with two beds and also common kitchen with a microwave, plates and cutlery everything! which helped us a lot. The bread, bananas and eggs were prepared for the guests which was nice. We met a lovely couple from Belgium there we enjoyed talking with them. We highly recommend ‘two bare feet’ for people visiting Winchester.
Scored 9.2
9.2
Rated superb
Superb
416 reviews
Price from
£132.25
per night
The Fox, hotel in Winchester

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

Breakfast selections exceeded expectation. Kingsize room was wonderful. staff very proffessional and happy in their services provided. Very helpfull manager who gave lots of advice on visiting destinations for days out. very quiet location but handy for accessing tourist destination
Scored 9.6
9.6
Rated exceptional
Exceptional
436 reviews
Price from
£159
per night
Idyllic Studio Flat, hotel in Winchester

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.

Gorgeous location. Well-equipped. Very comfortable bed and a good night’s sleep. Lovely welcome from Julie.
Scored 9.2
9.2
Rated superb
Superb
101 reviews
Price from
£85
per night
The Bugle Inn Twyford, hotel in Winchester

The Bugle Inn Twyford is set in Winchester, 12 km from Ageas Bowl, 17 km from The Mayflower Theatre, and 17 km from Southampton Guildhall.

Country in beautifully located
Scored 9.0
9.0
Rated superb
Superb
261 reviews
Price from
£150
per night
Millstream House, hotel in Winchester

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

Perfect walking distance for Winchester city centre. Lovely old house right on the river.
Scored 9.2
9.2
Rated superb
Superb
65 reviews
Price from
£241
per night
The Barrel Room at The Northbrook Arms, hotel in Winchester

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...

Nice, but fairly small room. Kitchen unit only has microwave - something you need to be aware of on Mondays & Tuesdays when the ub is closed. It´s quite a bit outside Winchester, which we didn´t mind though. Lovely village.
Scored 9.0
9.0
Rated superb
Superb
76 reviews
Price from
£88
per night
31 Queens Road, hotel in Winchester

31 Queens Road, a property with a garden and a shared lounge, is set in Winchester, 21 km from The Mayflower Theatre, 21 km from Southampton Guildhall, as well as 22 km from Southampton Cruise...

Everything. The location was close enough to walk to the centre, although the walk back up the hill wasn't the best. Richard certainly made us more than welcome & the breakfast was superb.
Scored 8.3
8.3
Rated very good
Very good
144 reviews
Price from
£96.50
per night
10 st james villas, hotel in Winchester

Situated in Winchester and only 19 km from The Mayflower Theatre, 10 st james villas features accommodation with garden views, free WiFi and free private parking.

Proprietor is a descendant of aviation pioneer A V Roe who developed numerous aircraft including the Lancaster bomber and the Avro Arrow. The presented memorabilia would be especially interesting for Canadians.
Scored 8.9
8.9
Rated fabulous
Fabulous
365 reviews
Price from
£110
per night
The Dolphin, hotel in Winchester

Located just 18 km from The Mayflower Theatre, The Dolphin offers accommodation in Winchester with access to a garden, a bar, as well as luggage storage space.

Nothing
Scored 7.5
7.5
Rated good
Good
248 reviews
Price from
£120.25
per night
Bell tent glamping at Marwell Resort, hotel in Winchester

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.

Tent was cosy and clean
Scored 7.9
7.9
Rated good
Good
196 reviews
Price from
£60
per night
All holiday rentals in Winchester

Most booked holiday rentals in Winchester this month

Enjoy breakfast in Winchester!

  • The Bugle Inn Twyford
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 261 reviews

    The Bugle Inn Twyford is set in Winchester, 12 km from Ageas Bowl, 17 km from The Mayflower Theatre, and 17 km from Southampton Guildhall.

    The super friendly staff, food and a room to die for

  • City Apartment
    Breakfast options
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 122 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
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 101 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.

    Really nice area, very private. Felt very comfortable

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

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

    So many lovely courses, totally loved every choice.

  • Two Bare Feet
    Breakfast options
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 416 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
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 65 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
    Scored 9.1
    9.1
    Rated superb
    Superb
     · 9 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
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 13 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.

These holiday rentals in Winchester have options with FREE cancellation

  • The Barrel Room at The Northbrook Arms
    Free cancellation options available
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 76 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.

  • 61
    Free cancellation options available
    Scored 7.6
    7.6
    Rated good
    Good
     · 263 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.

    I haven't had breakfast. That's my only complaint

  • 4 Bed City House with Private Garden and Parking
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 32 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
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 34 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.

    Immaculate. Could not have wished for more from a property rental.

  • Beautiful house on the River Itchen
    Free cancellation options available
    Scored 9.1
    9.1
    Rated superb
    Superb
     · 37 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.

  • Old School House, Winchester
    Free cancellation options available
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 17 reviews

    Situated in Winchester and only 22 km from The Mayflower Theatre, Old School House, Winchester features accommodation with garden views, free WiFi and free private parking.

    Clean and well located apartment with private parking. All commodities available in the apartment that makes you feel at home.

  • Sky View
    Free cancellation options available
    Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 40 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
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 13 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!

Highly rated holiday rentals in Winchester

  • The Nestle House
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 18 reviews

    Housed in a historic building, the recently renovated The Nestle House provides accommodation with a garden and free WiFi. A fitness room is available for guests.

    The attention to detail was exceptional from the host.

  • Cosy 1-Bed Escape with Free Parking - At Hem
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 26 reviews

    Cosy 1-Bed Escape with Free Parking - At Hem, 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

  • Tastefully Decorated 1-Bed with Free Parking - At Hem
    Scored 9.1
    9.1
    Rated superb
    Superb
     · 56 reviews

    Tastefully Decorated 1-Bed with Free Parking - At Hem 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
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 91 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.

  • Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 16
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 5 reviews

    Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 16 is set in Winchester, 12 km from Ageas Bowl, 17 km from The Mayflower Theatre, and 17 km from Southampton Guildhall.

  • Mallard Cottage
    8.0+ review score
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 11 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.

  • Queens Road Rental - Winchester Accommodation
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 5 reviews

    Set in Winchester, 21 km from The Mayflower Theatre and 21 km from Southampton Guildhall, Queens Road Rental - Winchester Accommodation offers accommodation with free WiFi, a garden, and access to a...

    The location was excellent. The property was clean and tidy and a small provisions pack made available.

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

    Walsingham House - Peaceful Elevated - Near Oram's Arbour is a recently renovated holiday home in Winchester, where guests can make the most of its garden and barbecue facilities.

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

FAQ about holiday rentals in Winchester

Holiday rentals that guests love in Winchester

  • Scored 8.9
    8.9
    Rated fabulous
    Fabulous
     · 25 reviews
    Nice holiday home close to the center of Winchester. Well equipped, nice terrace and view on the water. Very friendly and helpful hosts.
    Liesbeth
    Family with young children
  • Scored 7.5
    7.5
    Rated good
    Good
     · 248 reviews
    The village, and pub are very photogenic, Rooms are very spacious compared to most hotel rooms. Good fans downstairs in both apartments, but it was very hot for our 2 night stay and the upper bedrooms were stifling without their own fans, or the ability to open a window.
    Noel
    Group
  • Avg. price/night: £110
    Scored 8.9
    8.9
    Rated fabulous
    Fabulous
     · 365 reviews
    The location is fantastic, St James Villa is a 5 minute walk to Winchester city centre, but leafy and quiet and residential. The decor is quintessential English opulence. I love it, completely unique, one of a kind and with the best host. Alex is charming and the perfect host.
    Jenny
    Family with young children
  • Avg. price/night: £121
    Scored 7.7
    7.7
    Rated good
    Good
     · 680 reviews
    Lovely village & lovely property with very cosy & attractive rooms
    Jayne Louise
    Group
  • Avg. price/night: £159
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 436 reviews
    Village of Crawley sweet and walkable. Lovely facilities. The food was exceptional. Must also mention the housekeeper who served breakfast and gave us many touristic suggestions. She made us feel so welcome! The other staff was very helpful too.
    Cynthia
    Young couple
  • Avg. price/night: £159
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 436 reviews
    Lovely pub with rooms in an incredibly pretty village. Rooms lovely and nicely appointed, good sized bathroom all very clean. We had dinner there and it was fantastic with very good and friendly service to match. Breakfast was fabulous too and we got loads of tips and even leaflets on things to do in the area from a lovely lady who was working at breakfast. I would definitely return!
    Fabiana
    Young couple
  • Avg. price/night: £120
    Scored 8.9
    8.9
    Rated fabulous
    Fabulous
     · 79 reviews
    Beautiful old village pub serving meals had lunch it was great
    sheila
    Young couple
  • Avg. price/night: £159
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 436 reviews
    The staff at the Fox were exceptionally welcoming and friendly. The property is nestled in a charming village, offering a serene and private atmosphere. The rooms were impressively clean, with comfortable beds and ample space. The staff, particularly Tina during breakfast, exemplified genuine warmth, kindness, and attentiveness. The breakfast served was superb, leaving a lasting impression. I am certain to return and will wholeheartedly recommend this place to friends and family.
    Sipho
    Solo traveller
  • Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 11 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
  • Scored 9.0
    9.0
    Rated superb
    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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