Skip to main content

The best holiday homes in Winchester

Check out our pick of great holiday homes in Winchester

Filter by:

Review score

See the latest prices and deals by choosing your dates.
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.

Such a wonderful location with river & cathedral views and riverside walk into town. So beautiful and the perfect introduction to Winchester. Incredibly comfortable beds and Paula was a very helpful host.
Scored 9.2
9.2
Rated superb
Superb
66 reviews
Price from
£241
1 night, 2 adults
The Post Barn, beautiful barn conversion 10mins from Winchester, hotel in Winchester

Offering a garden and garden view, The Post Barn, beautiful barn conversion 10mins from Winchester is set in Sparsholt, 25 km from Southampton Guildhall and 26 km from Southampton Cruise Terminal.

Very clean and well equipped for a short stay.Lovely quiet location.Warm and homely.Short distance from Winchester which was the nearest large town.Would stay again and recommend to a friend.Overall a great place to stay and no real complaints about anything.
Scored 9.2
9.2
Rated superb
Superb
24 reviews
Price from
£170
1 night, 2 adults
4 bedrooms house for working Professionals, hotel in Winchester

Offering a garden and garden view, 4 bedrooms house for working Professionals is located in Southampton, 5.1 km from Southampton Guildhall and 5.7 km from Ageas Bowl.

Good location, spacious accommodation.
Scored 9.2
9.2
Rated superb
Superb
6 reviews
Price from
£169
1 night, 2 adults
The Annexe @ Mandalay Lodge, hotel in Winchester

Located in Medstead, the recently renovated The Annexe @ Mandalay Lodge provides accommodation 8.4 km from Jane Austen's House Museum and 25 km from Frensham Great Pond and Common.

Clean and well looked after
Scored 9.6
9.6
Rated exceptional
Exceptional
32 reviews
Price from
£127
1 night, 2 adults
Cosy cabin in Annie’s meadow, hotel in Winchester

Featuring garden views, Cosy cabin in Annie’s meadow provides accommodation with a garden and a balcony, around 15 km from Jane Austen's House Museum.

Lovely spacious cabin with amazing views over the countryside! Very friendly hosts, great hot tub, everything very comfortable.
Scored 9.6
9.6
Rated exceptional
Exceptional
35 reviews
Price from
£180
1 night, 2 adults
Mulberry Barn Annx - Self Contained Near Winchester, hotel in Winchester

Mulberry Barn Annx - Self Contained Near Winchester is located in Micheldever, 29 km from Jane Austen's House Museum, 34 km from The Mayflower Theatre, as well as 35 km from Southampton Guildhall.

Really lovely property, very rural but that was perfect for us. Very comfortable beds and spacious rooms.
Scored 8.3
8.3
Rated very good
Very good
63 reviews
Price from
£165
1 night, 2 adults
The Paddock View at Danebury, hotel in Winchester

Offering garden views, The Paddock View at Danebury is an accommodation located in Stockbridge, 23 km from Salisbury Train Station and 23 km from Salisbury Cathedral.

The caravan was very comfortable and reasonably priced
Scored 8.1
8.1
Rated very good
Very good
13 reviews
Price from
£87
1 night, 2 adults
Accessible 3-bedroom bungalow with patio +driveway, hotel in Winchester

Accessible 3-bedroom bungalow with patio +driveway, a property with a garden, is situated in Southampton, 5 km from The Mayflower Theatre, 5.1 km from Southampton Guildhall, as well as 5.8 km from...

Angelika the host was great, she answered all our questions before we arrived, her property was exactly what we wanted for a young family to enjoy for a few nights. Thanks
Scored 8.6
8.6
Rated fabulous
Fabulous
30 reviews
Price from
£212
1 night, 2 adults
The Retreat, a Luxury Riverside Cottage & garden, hotel in Winchester

Located just 3.7 km from Southampton Guildhall, The Retreat, a Luxury Riverside Cottage & garden features accommodation in Southampton with access to a garden, a shared lounge, as well as private...

Absolutely fantastic!!
Scored 8.8
8.8
Rated fabulous
Fabulous
62 reviews
Price from
£227
1 night, 2 adults
Luxury modern 1 bedroom house, hotel in Winchester

Located in Southampton, 600 metres from Southampton Guildhall and 2.2 km from Southampton Cruise Terminal, Luxury modern 1 bedroom house provides accommodation with amenities such as free WiFi and a...

The modern house in Southampton had a fully equipped kitchen, which was convenient even though we didn’t prepare any meals during our stay. The house was clean, and the large sofa provided a comfortable place to relax. The location was great, with supermarkets nearby and parking available for an additional fee just a few blocks away.
Scored 7.8
7.8
Rated good
Good
19 reviews
Price from
£95
1 night, 2 adults
All holiday homes in Winchester
Looking for a holiday home?
Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.
Search holiday homes in Winchester

Most booked holiday homes in Winchester this month

Enjoy breakfast in Winchester!

  • Stylish Stunning 2-BR Central Location, Sleeps 6, Winchester - By Blue Puffin Stays
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 5 reviews

    Offering a garden and garden view, Stylish Stunning 2-BR Central Location, Sleeps 6, Winchester - By Blue Puffin Stays is set in Winchester, 20 km from Southampton Guildhall and 22 km from Southampton...

    Very well presented property and excellent host communications. The property had everything one needed. A really excellent quality place with lots of space and very comfy sleeping. Definitely recommended

  • 2-BR Cosy Stunning Winchester Cottage Retreat with Garden, Near Cathedral! Sleeps 6, Pet Friendly with Parking - by Blue Puffin Stays
    Scored 9.9
    9.9
    Rated exceptional
    Exceptional
     · 7 reviews

    Set in Winchester, 21 km from The Mayflower Theatre, 2-BR Cosy Stunning Winchester Cottage Retreat with Garden, Near Cathedral!

  • Millstream House
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 66 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.

  • 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.

  • Sky View
    Breakfast options
    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
    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!

  • 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.

  • 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.

Save money on holiday homes in Winchester – budget options available!

  • Mallard Cottage
    Budget options available
    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.

  • 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

  • Designer's Town House
    Budget options available
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 13 reviews

    Set in Winchester, Designer's Town House is a historic holiday home that offers free WiFi, and guests can enjoy a garden and a terrace. With garden views, this accommodation provides a patio.

    Superb location Great size Very well fitted & superb amenities

  • Hang Your Hat
    Budget options available
    Scored 9.7
    9.7
    Rated exceptional
    Exceptional
     · 91 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

  • South House
    Budget options available
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 89 reviews

    South House is located in Winchester, on the border of the scenic South Downs National Park. Free WiFi access is available in this holiday home.

    location was perfect for central town and cathedral

  • Hyde Brewery House - 2 bedroom house with parking
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 10 reviews

    Set 22 km from Southampton Guildhall, 23 km from Southampton Cruise Terminal and 27 km from Jane Austen's House Museum, Hyde Brewery House - 2 bedroom house with parking features accommodation located...

    Great property but v admin happy. Huge deposit required. Didn’t see or speak to anyone. No toilet roll or salt n pepper

  • The Old Brewery Boardroom - Winchester City Centre, Free Parking for 2 Cars, Sleeps 6
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 10 reviews

    Housed in a historic building, the recently renovated The Old Brewery Boardroom - Winchester City Centre, Free Parking for 2 Cars, Sleeps 6 offers accommodation with a garden and free WiFi.

    Great location for sightseeing. Beautiful interiors and good facilities.

  • Queens Road Rental - Winchester Accommodation
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 6 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.

Great access to the city centre! Check these holiday homes in Winchester

  • Kingsgate Cottage
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Set in Winchester in the Hampshire region, Kingsgate Cottage features a terrace. This holiday home offers accommodation with a patio.

  • Piping Green 5 bedroom House
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Piping Green 5 bedroom House, a property with a garden, is set in Winchester, 15 km from The Mayflower Theatre, 16 km from Southampton Guildhall, as well as 17 km from Southampton Cruise Terminal.

  • House in historic Winchester
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 4 reviews

    House in historic Winchester, a property with a garden, is situated in Winchester, 22 km from The Mayflower Theatre, 22 km from Southampton Guildhall, as well as 23 km from Southampton Cruise Terminal...

    Very clean, with everything we needed. Perfect location.

  • Beggar's Lane Cottage
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 62 reviews

    Housed in a historic building, Beggar's Lane Cottage features accommodation with a garden and free WiFi in Winchester, 21 km from The Mayflower Theatre.

    Great location, close to town, bus routes and nature reserve.

  • Pemberly
    Central location
    Scored 8.3
    8.3
    Rated very good
    Very good
     · 7 reviews

    Situated 19 km from The Mayflower Theatre, Pemberly features accommodation with free WiFi and free private parking.

    Great location and surprisingly quiet nights sleep

  • Charming 4-Bed House in Winchester Free Parking
    Scored 7.3
    7.3
    Rated good
    Good
     · 3 reviews

    Offering a garden and garden view, Charming 4-Bed House in Winchester Free Parking is located in Winchester, 21 km from Southampton Guildhall and 23 km from Southampton Cruise Terminal.

  • The Old Sweet Shop
    Scored 7.0
    7.0
    Rated good
    Good
     · 1 review

    The Old Sweet Shop, a property with a garden, is situated in Winchester, 18 km from Southampton Guildhall, 20 km from Southampton Cruise Terminal, as well as 23 km from Ageas Bowl.

  • Charming Mews House in Historic Winchester

    Offering a garden and garden view, Charming Mews House in Historic Winchester is set in Winchester, 20 km from Southampton Guildhall and 21 km from Southampton Cruise Terminal.

  • Stylish 3BD Townhouse in Central Winchester

    Set 20 km from The Mayflower Theatre, Stylish 3BD Townhouse in Central Winchester offers accommodation with free WiFi and free private parking.

  • 59 Bar End Road

    Set 20 km from The Mayflower Theatre, 59 Bar End Road offers accommodation with free WiFi and free private parking.

  • 4 Bed in Redlynch 82799

    Set in Winchester and only 19 km from Salisbury Cathedral, 4 Bed in Redlynch 82799 offers accommodation with garden views, free WiFi and free private parking.

FAQ about holiday homes in Winchester

Holiday homes that guests love in Winchester

  • Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 95 reviews
    Central location, wonderful room, excellent walk in shower, all very clean. Parking permit sorted by host prior to arrival. Very helpful host with plenty of local knowledge - gave us lots of extra ideas about places to explore. Made for great weekend break.
    Chris
    Young couple
  • Avg. price/night: £126.65
    Scored 8.1
    8.1
    Rated very good
    Very good
     · 1,287 reviews
    Very clean, well appointed, excellent spa, friendly helpful staff.
    Yvette
    Solo traveller
  • Avg. price/night: £81
    Scored 7.1
    7.1
    Rated good
    Good
     · 3,493 reviews
    Location good for Winchester city and surrounding areas. Nice to have a swimming pool with a hotel. Room was large and cool. Beds very comfy. Towels nice white and fluffy. Bed linen very clean. Provided a upright fan. I had a settee in mine which made a change from lying on bed watching TV. Breakfast self service, but good selection of food
    Sally
    Solo traveller
  • Avg. price/night: £88
    Scored 8.5
    8.5
    Rated very good
    Very good
     · 1,231 reviews
    The room was lovely, very clean and inviting. A fan was provided but it was an exceptionally hot day/night.Staff were approachable, friendly and happy to help.
    Fenella
    Young couple
  • Avg. price/night: £125.10
    Scored 7.7
    7.7
    Rated good
    Good
     · 1,222 reviews
    Beautiful hotel, very clean, excellent service by all members of staff.
    Carl
    Solo traveller
  • Avg. price/night: £95
    Scored 8.9
    8.9
    Rated fabulous
    Fabulous
     · 1,485 reviews
    Really quirky theme, lovely big bed, very clean
    Catherine
    Young couple
  • Scored 8.1
    8.1
    Rated very good
    Very good
     · 19 reviews
    Very central. Excellent location. Kitchen was VERY clean and bedrooms very comfortable.
    Helen
    People with friends
  • Avg. price/night: £88
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 956 reviews
    The room was very clean and comfortable . We had evening meals as well as breakfast and the food was excellent . We stayed in Chisel room which had a balcony overlooking the beer garden .
    Michael
    Young couple
  • 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

Research, refine and make plans for your whole trip

gogless