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.

Lovely Views from front windows. Pretty river walks. Cosy, homely accommodation.
Scored 9.2
9.2
Rated superb
Superb
87 reviews
Price from
£241
1 night, 2 adults
The Post Barn, beautiful barn conversion 10mins from Winchester, hotel in Sparsholt

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.

Located in nice little village close to Winchester with a bus into town - bus stop right opposite the accommodation Great pub within a short walk Spotlessly clean accommodation and well equipped kitchen (though no oven) We had a great stay and it was perfect to visit Winchester Christmas market Prompt and helpful responses from the owner
Scored 8.8
8.8
Rated fabulous
Fabulous
27 reviews
Price from
£179.18
1 night, 2 adults
The Annexe @ Mandalay Lodge, hotel in Medstead

Offering a garden and garden view, The Annexe @ Mandalay Lodge is set in Medstead, 25 km from Frensham Great Pond and Common and 34 km from Ageas Bowl.

We loved the decor, the cosy bed and tv set up. Most of all we loved the log fire! Host was super friendly and very responsive. Would definitely stay again!
Scored 9.5
9.5
Rated exceptional
Exceptional
37 reviews
Price from
£126.75
1 night, 2 adults
Percy House Serviced Accommodation-Southampton, hotel in Southampton

Located 4 km from Southampton Guildhall, 5.5 km from Southampton Cruise Terminal and 11 km from Ageas Bowl, Percy House Serviced Accommodation-Southampton features accommodation set in Southampton.

It’s close to everything In Southampton
Scored 9.1
9.1
Rated superb
Superb
10 reviews
Price from
£256.87
1 night, 2 adults
Cosy cabin in Annie’s meadow, hotel in West Meon

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.

The great outdoors was my favourite part about this trip. It’s in a lovely area where nature greets you and there are plenty of areas to go for a lovely walk or a village pub with lovely fresh food. This place came with its own beauty and the cabin itself was cosy and welcoming. The cabin also provided entertainment from games and vinyls to having a radio.
Scored 9.6
9.6
Rated exceptional
Exceptional
37 reviews
Price from
£180
1 night, 2 adults
The Barn, hotel in Romsey

Offering a garden and garden view, The Barn is situated in Romsey, 18 km from The Mayflower Theatre and 18 km from Southampton Guildhall.

It's was peaceful, the host showed us around, despite living in the main house she gave us complete privacy. The barn is central to some nice locations for days out. Winchester, Southampton, Portsmouth and the New forest to name a few.
Scored 9.7
9.7
Rated exceptional
Exceptional
95 reviews
Price from
£134
1 night, 2 adults
Mulberry Barn Annx - Self Contained Near Winchester, hotel in Micheldever

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, and 35 km from Southampton Guildhall.

Lovely property for our stay. We stayed for one night for my daughter’s 9th birthday. Lovely location!
Scored 8.4
8.4
Rated very good
Very good
61 reviews
Price from
£165
1 night, 2 adults
4 bedrooms house for working Professionals, hotel in Southampton

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 size double bedrooms. Has the basics you need for a short stay. No issue with self check in. Has heating to make the place cosy. Good shower.
Scored 8.2
8.2
Rated very good
Very good
9 reviews
Price from
£170
1 night, 2 adults
Accessible 3-bedroom bungalow with patio +driveway, hotel in Southampton

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...

Cleanliness , heating system and smoking area at the back
Scored 8.6
8.6
Rated fabulous
Fabulous
35 reviews
Price from
£185.10
1 night, 2 adults
The Paddock View at Danebury, hotel in Stockbridge

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 7.8
7.8
Rated good
Good
15 reviews
Price from
£62.05
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.

Most booked holiday homes in Winchester this month

See all

Enjoy breakfast in Winchester!

  • Kingsgate Cottage
    Scored 9.6
    9.6
    Rated exceptional
    Exceptional
     · 5 reviews

    Set in Winchester in the Hampshire region, Kingsgate Cottage features a terrace. Guests staying at this holiday home have access to a patio.

  • WINTER SPECIAL OFFER!! Chic Stunning 2-BR Central Location, Sleeps 6, Winchester - By Blue Puffin Stays
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 6 reviews

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

    This property was everything we hoped for and more! Comfortable beds, a fully stocked kitchen, and interiors that felt like home. Can’t wait to return

  • 2-BR Chic Cosy Winchester Cottage Retreat with Garden, Near Cathedral! Sleeps 6, Pet Friendly with Parking - WINTER SPECIAL OFFER!! - 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 Chic Cosy Winchester Cottage Retreat with Garden, Near Cathedral!

  • 4 Bed City House with Private Garden and Parking
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 41 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.

    Comfy beds Lovely spacious and well laid out lounge are

  • Sky View
    Breakfast options
    Scored 9.4
    9.4
    Rated superb
    Superb
     · 49 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.

  • The Nestle House
    Scored 9.8
    9.8
    Rated exceptional
    Exceptional
     · 23 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. A fitness room is available for guests.

    Great location, great host, anything you would need

  • The Old Cook House
    Scored 9.0
    9.0
    Rated superb
    Superb
     · 12 reviews

    The Old Cook House, a property with a garden, is situated in Winchester, 21 km from Southampton Cruise Terminal, 24 km from Ageas Bowl, as well as 32 km from Jane Austen's House Museum.

    Excellent facilities, everything you’d have in your own home!

  • Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 14
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 5 reviews

    Birdsong Rural Winchester Twyford - 2BR, 5BR, 7BR - sleeps upto 14 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 9.7
    9.7
    Rated exceptional
    Exceptional
     · 11 reviews

    Mallard Cottage, a property with a garden, is situated in Winchester, 21 km from Southampton Guildhall, 22 km from Southampton Cruise Terminal, as well as 25 km from Ageas Bowl.

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

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

    Situated in Winchester, in a historic building, 21 km from Southampton Guildhall, Hang Your Hat is a holiday home with a garden and barbecue facilities.

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

  • South House
    Budget options available
    Scored 9.3
    9.3
    Rated superb
    Superb
     · 92 reviews

    Set in Winchester in the Hampshire region, South House has a patio. This property offers access to a balcony, free private parking and free WiFi.

    location was perfect for central town and cathedral

  • House in historic Winchester
    Scored 8.4
    8.4
    Rated very good
    Very good
     · 13 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.

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

    Hyde Brewery House - 2 bedroom house with parking is set in Winchester, 22 km from Southampton Guildhall, 23 km from Southampton Cruise Terminal, as well as 27 km from Jane Austen's House Museum.

    clean, comfortable beds, warm and great well stocked kitchen

  • The Old Brewery Boardroom - Winchester City Centre - Unique Property - Free Parking - Sleeps 6 - by XPlus Stays
    Scored 8.8
    8.8
    Rated fabulous
    Fabulous
     · 16 reviews

    Housed in a historic building, the recently renovated The Old Brewery Boardroom - Winchester City Centre - Unique Property - Free Parking - Sleeps 6 - by XPlus Stays offers accommodation with a garden...

    Great location for sightseeing. Beautiful interiors and good facilities.

  • Charming 4-Bed House in Winchester Free Parking
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 5 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.

  • Beggar's Lane Cottage
    Budget options available
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 57 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.

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

  • Charming Mews House in Historic Winchester
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 1 review

    Offering a garden and city 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
    Scored 10.0
    10.0
    Rated exceptional
    Exceptional
     · 2 reviews

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

  • 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.

  • Millstream House
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 87 reviews

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

    The property met every single need! Great location

  • Winchester City House
    Scored 8.0
    8.0
    Rated very good
    Very good
     · 1 review

    Offering garden views, Winchester City House is an accommodation situated in Winchester, 21 km from Southampton Guildhall and 22 km from Southampton Cruise Terminal.

  • Queens Road Rental - Winchester Accommodation
    Scored 7.8
    7.8
    Rated good
    Good
     · 7 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...

    Thank you, I had a very comfy and peaceful stay with everything I needed provided.

  • 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, 20 km from Southampton Cruise Terminal, 23 km from Ageas Bowl, as well as 30 km from Jane Austen's House Museum.

  • Cosy Apartment
    Central location

    Cosy Apartment is set in Winchester, 21 km from Southampton Cruise Terminal, 25 km from Ageas Bowl, as well as 27 km from Jane Austen's House Museum.

  • The Loft Winchester

    The Loft Winchester is situated in Winchester, 21 km from The Mayflower Theatre, 21 km from Southampton Guildhall, and 22 km from Southampton Cruise Terminal.

  • Winchester Stunning Spacious 4 Bedroom House

    Set in Winchester in the Hampshire region, Winchester Stunning Spacious 4 Bedroom House has a terrace. Offering a garden, the property is located within 20 km of Southampton Guildhall.

  • 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

See all
  • Scored 9.5
    9.5
    Rated exceptional
    Exceptional
     · 97 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: £118.15
    Scored 8.1
    8.1
    Rated very good
    Very good
     · 1,655 reviews
    Very clean, well appointed, excellent spa, friendly helpful staff.
    Yvette
    Solo traveller
  • Avg. price/night: £49.50
    Scored 7.1
    7.1
    Rated good
    Good
     · 3,305 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: £85
    Scored 8.6
    8.6
    Rated fabulous
    Fabulous
     · 1,110 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: £105
    Scored 7.6
    7.6
    Rated good
    Good
     · 1,427 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
     · 1,535 reviews
    Really quirky theme, lovely big bed, very clean
    Catherine
    Young couple
  • Scored 7.9
    7.9
    Rated good
    Good
     · 24 reviews
    Very central. Excellent location. Kitchen was VERY clean and bedrooms very comfortable.
    Helen
    People with friends
  • Avg. price/night: £84.38
    Scored 9.2
    9.2
    Rated superb
    Superb
     · 982 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 9.7
    9.7
    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