Self catering accommodation in Winchester and Cottages - Holiday Lettings - Holiday Rentals Winchester

Close

View larger map

Also consider

Europe Holidays
473233 properties
United Kingdom Holidays
62360 properties
Winchester Holidays
34 properties
Cottages Cornwall
2983 properties
Apartments Greater London
941 properties
Cottages Cumbria / Lake District
940 properties
Cottages Devon
2810 properties
Cottages Central England / Cotswolds
940 properties
Cottages Dorset
819 properties
Cottages Isle of Wight
507 properties
Cottages Peak District / Derbyshire
460 properties
Cottages Somerset
610 properties
Cottages Kent
557 properties
Cottages Sussex
770 properties
Cottages Norfolk
1023 properties
Cottages Isle of Man
11 properties
Northumberland
640 properties
Cottages Yorkshire / Yorkshire Dales
1496 properties
Cottages England
41760 properties
Cottages Scotland
7758 properties
Apartments Edinburgh
1385 properties
Cottages Wales
7155 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

323 Holiday homes

(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

£1,330 / week

Book View

Responds fast!
avg. 1 hour 39 minutes

from £190 / night

21

Holiday lodge with golf nearby in Winchester

Hampshire / Winchester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 20 km
  • Child friendly
  • Pet friendly

from £123 / night

£735 - £1,335 / week

Book View

from £123 / night

(5) Excellent 

17

Home rental in Winchester

Hampshire / Winchester

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary

from £175 / night

£995 - £1,500 / week

Book View

from £175 / night

(8) Excellent 

9

Winchester holiday b&b rental

Hampshire / Winchester

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
“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

from £65 / night

£455 / week

Book View

Responds fast!
avg. 3 hours 53 minutes

from £65 / night

(19) Excellent 

Certificate of Excellence

27

Holiday cottage rental

Winchester / Pitt

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 30 km
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £120 / night

£560 - £947 / week

Book View

Responds fast!
avg. 2 hours 52 minutes

from £120 / night

(7) Very Good 

14

Holiday home in Winchester

Hampshire / Winchester

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
“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 w
…see more

from £102 / night

£714 / week

Book View

from £102 / night

(5) Excellent 

11

Winchester holiday apartment let

Hampshire / Winchester

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly

from £155 / night

£980 / week

Book View

from £155 / night

12

Holiday home in Winchester

Hampshire / Winchester

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
  • Private garden

from £73 / night

£505 - £846 / week

Enquire View

from £73 / night

(19) Excellent 

16

Holiday penthouse rental

Hampshire / Winchester

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Car not necessary
“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 ap
…see more

from £200 / night

£1,100 - £1,800 / week

Book View

Responds fast!
avg. 2 hours 45 minutes

from £200 / night

(9) Excellent 

15

Winchester holiday cottage accommodation

Hampshire / Winchester

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • 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 £90 / night

£630 / week

Book View

from £90 / night

(9) Excellent 

Certificate of Excellence

17

Holiday guest house in Winchester

Hampshire / Winchester

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 25 km
  • Pet friendly

Certificate of Excellence

from £100 / night

£560 - £630 / week

Book View

Responds fast!
avg. 2 hours 52 minutes

from £100 / night

(5) Very Good 

41

Winchester holiday barn rental

Hampshire / Winchester

1 2 2 nights min

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

from £125 / night

£850 / week

Book View

Responds fast!
avg. 2 hours 9 minutes

from £125 / night

29

Holiday townhouse in Winchester

Hampshire / Winchester

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden

from £169 / night

£1,182 - £1,231 / week

Book View

from £169 / night

(4) Excellent 

15

Holiday apartment in Winchester

Hampshire / Winchester

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary

from £90 / night

£535 - £600 / week

Book View

Responds fast!
avg. 3 hours 29 minutes

from £90 / 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

from £123 / night

£861 / week

Book View

from £123 / night

(12) Excellent 

18

Log cabin rental in Winchester

Hampshire / Winchester

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • 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 £60 / night

£350 / week

Book View

Responds fast!
avg. 3 hours 47 minutes

from £60 / night

7

Winchester holiday home rental

Hampshire / Winchester

5 10 2 nights min

  • 5 bedrooms
  • Sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £700 / night

£2,300 / week

Book View

Responds fast!
avg. 2 hours 31 minutes

from £700 / night

(10) Very Good 

18

Holiday cottage in Winchester

Hampshire / Winchester

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Car not necessary
  • Private garden
“Recent Stay” We thought the cottage was very convenient and at the right end of Winchester . It suited our needs.
…see more

from £150 / night

£895 / week

Book View

from £150 / night

(27) 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
“Xmas 2015” Stayed hear with my husband, son and his girlfriend when visiting my family over Christmas. The apartment was clean, very well equipped and in a good location. Would stay here again.
…see more

from £110 / night

£725 - £810 / week

Enquire View

from £110 / night

(21) Excellent 

8

Holiday home in Winchester

Hampshire / Winchester

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly

from £335 / night

£2,345 / week

Book View

from £335 / night

(9) Excellent 

20

Holiday log cabin rental

Hampshire / Winchester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 20 km
  • Child friendly
  • Pet friendly
“Clean, light, bright and spacious even though the weather was wet” Went to stay for a week with my sisters, mother and a small dog! Really lovely clean and spacious accommodation with comfy beds. The kitchen was fairly well equipped, although no veget
…see more

from £123 / night

£735 - £1,335 / week

Book View

from £123 / night

(14) Very Good 

16

Holiday apartment with golf nearby in Winchester

Hampshire / Winchester

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Car not necessary
“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 othe
…see more

from £110 / night

£625 - £765 / week

Book View

from £110 / night

33

Holiday home rental

Hampshire / Winchester

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly

from £200 / night

£1,396 - £1,543 / week

Book View

from £200 / night

(8) Excellent 

13

Holiday log cabin rental

Hampshire / Winchester

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 20 km
  • Child friendly
  • Pet friendly

from £155 / night

£660 - £1,185 / week

Book View

from £155 / night

17

Holiday apartment in Winchester

Hampshire / Winchester

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min

from £159 / night

£1,112 - £1,210 / week

Book View

from £159 / night

(2) Excellent 

21

Holiday lodge with golf nearby in Winchester

Hampshire / Winchester

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly

from £143 / night

£800 - £1,400 / week

Book View

from £143 / night

11

Holiday home in Winchester

Hampshire / Winchester

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly

from £186 / night

£1,299 - £1,446 / week

Book View

from £186 / night

14

Holiday log cabin with golf nearby in Winchester

Hampshire / Winchester

2 4 28 nights min

  • 2 bedrooms
  • Sleeps 4
  • 28 nights min
  • Child friendly
  • Pet friendly

from £86 / night

£600 / week

Book View

from £86 / night

12

Holiday log cabin with golf nearby in Winchester

Hampshire / Winchester

3 6 28 nights min

  • 3 bedrooms
  • Sleeps 6
  • 28 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

from £96 / night

£670 / week

Book View

from £96 / night

7

Holiday home in Winchester

Hampshire / Winchester

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly

from £148 / night

£1,031 - £1,080 / week

Book View

from £148 / night

(4) Excellent 

Certificate of Excellence

21

Holiday home in Winchester

Hampshire / Winchester

3 6 2 nights min

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

Certificate of Excellence

from £190 / night

£1,330 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £190 / night

(34) Excellent 

16

Holiday cottage rental

Hampshire / Winchester

1 3 2 nights min

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

from £145 / night

£950 - £1,370 / week

Book View

Responds fast!
avg. 3 hours 33 minutes

from £145 / night

(7) Very Good 

11

Holiday b&b in Winchester

Hampshire / Winchester

1 2 1 night min

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

from £80 / night

£500 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from £80 / night

7

Holiday apartment in Winchester

Hampshire / Winchester

1 2 2 nights min

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

from £85 / night

£500 / week

Book View

Responds fast!
avg. 2 hours 24 minutes

from £85 / night

Why Winchester?

Based in the county of Hampshire, England, Winchester is a city steeped in history. With cultural landmarks, family attractions and more, book your holiday rental in Winchester today and enjoy an action-packed trip to this beautiful city.

About Winchester

Winchester has been the setting for many novels, including The Whole Day Through by Patrick Gale and One Day by David Nicholls.

What to Do

Winchester Science Centre and Planetarium has over 100 exhibitions where you can discover more about the universe. You can also find out more about the human body as well as live shows and workshops.

Top Winchester Travel Tips

Take a visit to the stunning city of Winchester and marvel at the exquisite range of attractions on offer. Book your holiday rental in Winchester today to enjoy one of the best historic and cultural cities within the UK.

Top Destination reviews

The Old Tractor Barn, Crabwood Cottages
The old tractor barn

Had a wonderful week exploring the south of England . The weather was amazing and most importantly the cottage was superb ! Every need catered for ! lovely friendly hosts- perfect for our family of 5! Was really sad to leave … see more
Hang Your Hat - classy hideaway in Winchester
A great place to Hang your Hat

Winchester is a walking city full of history and Hang your Hat is a great place to start and finish any walk . Perfect location . on street permit ( supplied ) parking , great modern amenities in a 160 year old renovated cottage and the owner Mike a semi retired medical professional is very helpful with immense local knowledge and takes great care and pride in the property. Only thing that could have been better was the weather . Thanks Mike it was great. John and Marlene Adelaide Australiasee more
Cosy character cottage in central Winchester
It was a little nice cottage, we were all very happy

The Furniture is simple but functional and aestethic Located near by the attractions of Winchester as Cathedral etc and near by the Itchen with a attractive footpath along the river Winchester has a lot of nice Restaurants and Pubs all near the cottage We cooked often, the kitchen was good equipped, apart from the knifes...We bought 2 and left them in the kitchen. I hope you understand my english, perhaps I did not use the right words. In this case sorry about eventually misunderstandingssee more
The Down House Cottage
Comfortable and charming

Adequate kitchen equipment, cosy lounge with large wood burning stove and snug bedroom. Super Bathroom shower. Well positioned for access to Winchester and Hampshire including 1/2 hour to dockyard exhibits at Portsmouth. … see more
two bare feet
Quirky and great fun

Wonderful property - very unusual. Beautifully clean and beds very comfortable: excellent location in the centre of Winchester … see more
Idyllic Hampshire Hideaway - The Orchard Studio
A delightful stay.

What an amazing place, everything you could wish for. Beautiful garden, wonderful breakfast and perfect for our two dogs. Lovely walks on the doorstep. Local pub had great food and dog friendly. Victoria, the owner, was lovely and very welcoming. Would highly recommend Orchard Studio. It is a very special place. One review I read before I booked said it was uber cute and that is exactly what it was. Have to say it was just perfect. Many thanks.see more