Self catering accommodation in Winchester and cottages – Holiday Lettings - Holiday Rentals Winchester

Close

View larger map

Also consider

Europe Holidays
430742 properties
United Kingdom Holidays
55805 properties
England Holidays
40729 properties
Cottages Cornwall
2983 properties
Apartments Greater London
941 properties
Cottages Cumbria / Lake District
940 properties
Houses Devon
2810 properties
Cottages Central England / Cotswolds
940 properties
Houses Dorset
819 properties
Houses Isle of Wight
507 properties
Cottages Peak District / Derbyshire
460 properties
Houses Somerset
610 properties
Houses Kent
557 properties
Houses Sussex
770 properties
Houses Norfolk
1023 properties
Cottages Isle of Man
11 properties
Northumberland
640 properties
Houses Yorkshire / Yorkshire Dales
1496 properties
Coastal Cottages
222 properties

Winchester

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

37 Holiday homes

(25) Very Good 

35

Holiday bungalow in Winchester

Hampshire / Winchester

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
“Excellent weekend break away” The accommodation was clean and fully kitted with all your amenities. Hosts were very welcoming. We were lucky enough to have lovely weather so enjoyed sitting in the garden and hot tub! Would definitely recommend to  …see more

from £120 / night

£825 - £1415 / week

Book View

from £120 / night

(7) Excellent 

18

Log cabin rental in Winchester

Hampshire / Winchester

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Suitable for children age 5+
  • Car not necessary
“Fabulous Winchester” My mother and I stayed in Winchester for a week. The city itself is beautiful, very historic, has a lovely atmosphere. We also spent a day touring the New Forest and spent an afternoon in Lymington, which is quaint, nice marina ar  …see more

from £50 / night

£300 - £350 / week

Book View

from £50 / night

(5) Excellent 

17

Holiday guest house in Winchester

Hampshire / Winchester

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask owner if suitable for children
  • Ask about pets
The Hayloft is one of 3 cottages within Crabwood Cottages. It has been tastefully converted with fabulous views over rolling fields and forest, perfect for couples or overnight business trips. The Hayloft is situated right on a bridleway leading to wonderful woodland  …see more

from £85 / night

£450 - £600 / week

Book View

from £85 / night

(4) Excellent 

27

Twyford holiday cottage rental

Twyford / Twyford

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Private garden
Peacefully situated on a 4 acre smallholding in the depths of the Hampshire countryside, yet only 7 miles from Winchester, The Stables provide exceptionally well thought-out, beautifully presented accommodation.  …see more

from £97 / night

£417 - £699 / week

Enquire View

from £97 / night

(4) Excellent 

11

Winchester holiday apartment let

Hampshire / Winchester

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
Stunning contemporary apartment in central Winchester, sleeping 5. Newly refurbished and just minutes from the town centre and train station it is in an ideal location for exploring the historic town and the surrounding countryside.<br />Winchester is packed with  …see more

from £155 / night

£980 / week

Book View

from £155 / night

(15) Excellent 

27

Holiday cottage rental

Winchester / Pitt

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
The Old Tractor Barn is one of 3 cottages within Crabwood Cottages. It is a fabulous holiday cottage set in farmland with wonderful views of horses grazing in rolling paddocks and chickens pecking around the old farmyard and direct access on to a bridleway.The location  …see more

from £95 / night

£485 - £795 / week

Book View

from £95 / night

4

Holiday home in Winchester

Hampshire / Winchester

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
period cottage with enclosed courtyard garden in central location, sleeps 2+2 this red brick victorian property forms part of an historic conservation area at the heart of winchester, with the mainline train station just 300 yards. Lovingly fitted...  …see more

from £75 / night

£525 - £795 / week

Enquire View

from £75 / night

(8) Excellent 

15

Winchester holiday cottage accommodation

Hampshire / Winchester

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask owner if suitable for children
  • Car not necessary
  • Private garden
“Dr” We spent a lovely five nights at this adorable little cottage: the interior is as described and both tasteful and comfortable. The cottage is well-situated in the Hampshire hills: we had a wonderful rural walk along the River Itchen and a great da  …see more

from £85 / night

£595 / week

Book View

from £85 / night

(5) Very Good 

21

Holiday cottage in Winchester

Hampshire / Winchester

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
“A sweet little house” A sweet little house in the centre of Winchester. The house was well equipped and clean. Had all mod cons including wifi.  …see more

from £128 / night

£895 / week

Book View

from £128 / night

(7) Very Good 

21

Cottage rental in Winchester

Twyford / Twyford

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
“Cosy house in the countryside” Well equiped house with garden located in a village not far to train station to move around South England. Easy access to Winchester and pathways of South Downs NP.  …see more

from £150 / night

£625 - £795 / week

Book View

from £150 / night

(8) Excellent 

17

Holiday home rental

Hampshire / Winchester

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
“A well appointed house in central Winchester” The house is well situated in walking distance to Winchester Cathedral and the High street. The house is brilliant, a good sized, well appointed kitchen. Very comfortable bedrooms and living room. I loved  …see more

from £190 / night

£1330 / week

Book View

from £190 / night

(17) Excellent 

16

Holiday penthouse rental

Hampshire / Winchester

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Car not necessary
“Great Place and location” we both really enjoyed our stay. Gordon, the owner, could not have been more helpful. Everything you could want to enjoy a great city with fabulous restaurants all around just everything was in walking distance. Beds were c  …see more

from £180 / night

£1200 / week

Book View

from £180 / night

(3) Very Good 

18

Home rental in Winchester

Hampshire / Winchester

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
Unique stylish contemporary holiday home filled with light from windows on all sides.Off street parking available, but train station short walk away, so car not essential.Comfortable home from home accommodation for a family .<br />Winchester is a city with much t  …see more

from £150 / night

£950 - £1500 / week

Book View

from £150 / night

(10) Very Good 

19

Holiday apartment with golf nearby in Winchester

Hampshire / Winchester

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
“Right in the heart of Winchester” A small flat which is located right in the centre of Winchester.. Very convenient location. although small the flat appeared to be well equipped and included wifi and parking.  …see more

from £95 / night

£525 - £765 / week

Book View

from £95 / night

(2) Excellent 

14

Holiday home in Winchester

Hampshire / Winchester

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
“Cosy say in Granary Cottage” Great accommodation, everything we needed the kitchen was very well equipped Had a problem with the Wi Fi but otherwise a great stay. Located well for visiting Winchester and the surrounding areas. Owners very helpful an  …see more

from £102 / night

£714 / week

Book View

from £102 / night

7

Winchester holiday home rental

Hampshire / Winchester

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Riverside Cottage is away from the maddening crowd yet easy access to Winchester, Andover, London with lots of local interest too It is an old thatched cottage set in 8 acres and on the River Dever. It overlooks fields and so private and relaxing. Riverside also ha  …see more

from £700 / night

£2300 / week

Book View

from £700 / night

29

Holiday townhouse in Winchester

Hampshire / Winchester

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden
This stylish and very well presented town-house is within walking distance of Winchester town centre and its wonderful amenities. The property benefits from a courtyard garden, roof terraces, balcony and secure under croft allocated parking. At street level there is und  …see more

from £169 / night

£1182 - £1231 / week

Book View

from £169 / night

7

Holiday apartment in Winchester

Hampshire / Winchester

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
This distinctive period house dates back to circa 1900 when it was originally the front office of the Winchester Brewery. The property has since been sympathetically converted to provide a wonderful house which has retained some lovely period features, including wood pa  …see more

from £175 / night

£1225 / week

Book View

from £175 / night

(24) Excellent 

8

Holiday apartment in Winchester

Hampshire / Winchester

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
“Very well equipped ,spacious, clean and cheerful.” Very prompt contact. Clear instructions on how to find and get into the flat. Accessed via stairs. Walking distance into the centre. Parking space and access to it is tight but manageable. Quiet ap  …see more

from £105 / night

£660 - £770 / week

Enquire View

from £105 / night

6

Holiday b&b in Winchester

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
The rooms are fitted with a flat-screen TV and DVD player. You will find a coffee machine in the room. Every room is fitted with a private bathroom. For your comfort, you will find free toiletries and a hairdryer. Winchester Crown Court is 400 metres from Saskia's  …see more

from £90 / night

£630 / week

Book View

from £90 / night

14

Holiday lodge rental

Hampshire / Winchester

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Old Orchard is one of 3 accommodations within Crabwood Cottages. It is a peaceful rural holiday accommodation with lovely views and wonderful forest walks on your doorstep, yet perfectly located to explore The South of England and nearby cathedral city of Winchester  …see more

from £120 / night

£700 - £3840 / week

Book View

from £120 / night

(4) Excellent 

9

Winchester holiday b&b rental

Hampshire / Winchester

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
“Fabulous find - a real gem” The studio is absolutely perfect. We had the most wonderful three night stay. Fabulous space, idyllic garden, great location and beautifully quiet. Victoria and her family were so welcoming and the breakfast was amazing. De  …see more

from £65 / night

£455 / week

Book View

from £65 / night

7

Holiday b&b in Winchester

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
The rooms are fitted with a flat-screen TV and DVD player. You will find a coffee machine in the room. Every room is fitted with a private bathroom. For your comfort, you will find free toiletries and a hairdryer. Winchester Crown Court is 400 metres from Saskia'  …see more

from £95 / night

£665 / week

Book View

from £95 / night

(4) Excellent 

24

Winchester holiday barn rental

Hampshire / Winchester

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Pet friendly
Beautifully converted timber barn in the heart of the Test Valley. The Test Way on your doorstep for miles of country walks. Ideal country retreat for fishing, shooting, walking, cycling, dogs and families. luxury accommodation with parking, gardens and balcony.  …see more

from £125 / night

£800 / week

Book View

from £125 / night

(14) Excellent 

8

Holiday home in Winchester

Hampshire / Winchester

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
Prices for a single room start from £95 Prices for the whole house start from £335 two bare feet Winchester offers loft-style living to those looking for a break with friends and family or to those travelling with work. Each of the 3 individually styled bed  …see more

from £335 / night

£2345 / week

Book View

from £335 / night

7

Holiday home in Winchester

Hampshire / Winchester

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
DETAILS FOR NO. 12 ST CLEMENT STEET Holiday Cottage in Winchester UK at No. 12 St Clement Street "Honeysuckle". A delightful period cottage believed to date back to the 1800's, located in the heart of the City and within walking distance of the High Stre  …see more

from £148 / night

£1031 - £1080 / week

Book View

from £148 / night

11

Holiday home in Winchester

Hampshire / Winchester

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
DETAILS NO. 79 TOWER STREET Holiday Home in Winchester UK is charming period property with a City Centre location making it an ideal holiday home. You and your family can enjoy this holiday home in Winchester and all the city centre has to offer being just a stone'  …see more

from £186 / night

£1299 - £1446 / week

Book View

from £186 / night

20

Holiday shepherds hut in Winchester

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
Rent this beautiful shepherds hut set in a idyllic location of a private four acre field with access to a its own woodlands. Discover and enjoy the natural wildlife that surrounds the hut including an active badger set, rabbits, hares, pheasant and wild deer or spot  …see more

from £65 / night

£400 / week

Book View

from £65 / night

9

Holiday home rental

Hampshire / Winchester

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
DETAILS NO. 73 TOWER STREET Holiday Home in Winchester UK at No. 73 Tower Street No. 73 Tower Street has a really great city centre location as holiday home in Winchester because it is situated within a few minutes walk of the Railway Station, Discovery Centre, Theatre  …see more

from £186 / night

£1299 - £1348 / week

Book View

from £186 / night

33

Holiday home rental

Hampshire / Winchester

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
DETAILS NO. 02 BECKS MEWS No. 02 Becks Mews - Sleeping 4-7 people is a modern mews house perfectly placed self catering accommodation within minutes walk of the station. The bespoke doors, leaded dormers and the appearance of the house is smart, attractive and appropr  …see more

from £200 / night

£1396 - £1543 / week

Book View

from £200 / night

47

Holiday apartment in Winchester

Hampshire / Winchester

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask owner if suitable for children
Situated within a former warehouse building converted in 1973, this serviced apartment offers great accommodation for 4 on the 2nd floor (with lift) and is surprisingly quiet for the heart of the City. FACILITIES NO. 11 COSSACK LANE HOUSE Apartment located on the 2nd fl  …see more

from £123 / night

£861 / week

Book View

from £123 / night

17

Holiday apartment in Winchester

Hampshire / Winchester

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
DETAILS NO. 01B 1 CLIFTON TERRACE Holiday Apartment in Winchester UK at No. 01B 1 Clifton Terrace. No. 01B 1 Clifton Terrace is a light and attractive 1st floor apartment situated in the heart of central Winchester in a popular and elevated residential area immediatel  …see more

from £159 / night

£1112 - £1210 / week

Book View

from £159 / night

10

Winchester / Kings Worthy

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly

 …see more

from £90 / night

£630 / week

Book View

from £90 / night

(3) Very Good 

21

Hampshire / Winchester

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly

 …see more

from £190 / night

£1330 / week

Book View

from £190 / night

44

Hampshire / Winchester

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary

 …see more

from £120 / night

£825 - £1415 / week

Book View

from £120 / night

(6) Very Good 

11

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Nearest beach 45 km
  • Car not necessary
  • Air conditioning

 …see more

from £90 / night

£700 / week

Book View

from £90 / night

(29) Excellent 

16

Hampshire / Winchester

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Private garden

 …see more

from £145 / night

£950 - £1370 / week

Book View

from £145 / night

Top Destination reviews

Garden Apartment in Winchester
Excellent accommodation ideally placed for exploring Winchester

This is ideal accommodation for a base from which to explore Winchester, located just a few minutes walk from the town centre in one direction and close by the main city park in the other. The apartment is well appointed and we were welcomed by flow … see more
The Sky Penthouse
Beautiful Apartment

Myself and the family stayed at the Sky Penthouse for my graduation. The owners, Gordon and his wife, were both very warm and welcoming. Any questions or queries were met with with a fast and helpful reply via text message. The apartment it-self was … see more
South House Winchester
A well appointed house in central Winchester

The house is well situated in walking distance to Winchester Cathedral and the High street. The house is brilliant, a good sized, well appointed kitchen. Very comfortable bedrooms and living room. I loved the knitted blankets in the twin room! … see more
The Granary Annex at Worthy Barn
Comfortable accommodation with welcoming owners

We chose this holiday cottage because of: Modern spacious design, No dogs, No smoking and Wi-fi available + easy access to Winchester. The cafe and shop opposite was also a bonus. The owners next door were very responsive to our needs and queries. … see more
The Down House Cottage
Dr

We spent a lovely five nights at this adorable little cottage: the interior is as described and both tasteful and comfortable. The cottage is well-situated in the Hampshire hills: we had a wonderful rural walk along the River Itchen and a great day o … see more
Idyllic Hampshire Hideaway - The Orchard Studio
Lovely pet friendly holiday B&B

We stayed over the Christmas holiday, warm,cosy welcome even Christmas decorations, everything we needed and more. … see more