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359 Holiday homes

25

Holiday home in Winchester

Hampshire / Winchester

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly

from £132 / night

£922 / week

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from £132 / night

(6) 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 £161 / night

£974 / week

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from £161 / night

(14) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £69 / night

£401 / week

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Responds fast!
avg. 2 hours 59 minutes

from £69 / night

12

Holiday home in Winchester

Hampshire / Winchester

2 3 7 nights min

  • 2 bedrooms
  • sleeps 3
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £73 / night

£505 - £846 / week

Enquire View

from £73 / night

(11) Very Good 

Certificate of Excellence

14

Holiday home in Winchester

Hampshire / Winchester

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly

Certificate of Excellence

from £117 / night

£818 / week

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from £117 / night

(10) Excellent 

22

Holiday guest house in Winchester

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 25 km
  • Pet friendly

from £98 / night

£619 - £699 / week

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Responds fast!
avg. 1 hour 29 minutes

from £98 / night

(9) Excellent 

15

Holiday apartment in Winchester

Hampshire / Winchester

1 2 2 nights min

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

from £103 / night

£642 - £727 / week

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Responds fast!
avg. 2 hours 25 minutes

from £103 / night

(18) Very Good 

16

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

from £126 / night

£682 - £1,082 / week

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from £126 / night

(9) 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 £201 / night

£1,117 - £1,718 / week

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from £201 / night

20

Holiday cottage in Winchester

Hampshire / Winchester

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden

from £359 / night

£1,029 - £1,597 / week

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from £359 / night

(8) Very Good 

11

Winchester holiday apartment let

Hampshire / Winchester

3 5 2 nights min

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

from £178 / night

£1,123 / week

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from £178 / night

(29) 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

from £110 / night

£725 - £810 / week

Enquire View

from £110 / night

(2) Excellent 

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 £141 / night

£809 - £1,780 / week

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from £141 / night

(3) Very Good 

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 £164 / night

£913 - £2,044 / week

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from £164 / night

(21) Excellent 

Certificate of Excellence

31

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 £100 / night

£573 - £911 / week

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Responds fast!
avg. 1 hour 29 minutes

from £100 / 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 £802 / night

£2,634 / week

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Responds fast!
avg. 3 hours 1 minutes

from £802 / 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

from £103 / night

£722 / week

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from £103 / night

(11) Excellent 

7

Winchester holiday b&b rental

Hampshire / Winchester

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £86 / night

£602 / week

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Responds fast!
avg. 2 hours 39 minutes

from £86 / 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

from £218 / night

£1,523 / week

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Responds fast!
avg. 1 hour 35 minutes

from £218 / 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 £194 / night

£1,354 - £1,410 / week

Book View

from £194 / night

(11) Very Good 

18

Holiday cottage in Winchester

Hampshire / Winchester

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Car not necessary
  • Private garden

from £172 / night

£911 - £1,025 / week

Book View

from £172 / night

(21) Excellent 

16

Holiday penthouse rental

Hampshire / Winchester

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Car not necessary

from £287 / night

£1,203 / week

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Responds fast!
avg. 2 hours 8 minutes

from £287 / 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

from £141 / night

£813 - £1,764 / week

Book View

from £141 / night

11

Holiday home in Winchester

Hampshire / Winchester

2 7 7 nights min

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

from £213 / night

£1,488 - £1,656 / week

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from £213 / night

17

Holiday apartment in Winchester

Hampshire / Winchester

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min

from £182 / night

£1,274 - £1,386 / week

Book View

from £182 / 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 £166 / night

£724 - £1,563 / week

Book View

from £166 / 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 £141 / night

£986 / week

Book View

from £141 / night

20

Holiday home rental

Hampshire / Winchester

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly

from £227 / night

£1,078 - £1,519 / week

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from £227 / night

19

Holiday home rental

Hampshire / Winchester

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly

from £154 / night

£762 - £1,110 / week

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from £154 / night

13

Apartment rental in Winchester

Hampshire / Winchester

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 40 km
  • Car not necessary

from £144 / night

£802 / week

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from £144 / night

15

Holiday home letting

Hampshire / Winchester

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly

from £239 / night

£881 - £1,319 / week

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from £239 / night

11

Holiday home rental

Hampshire / Winchester

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly

from £115 / night

£802 / week

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from £115 / night

25

Winchester holiday home rental

Hampshire / Winchester

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly

from £513 / night

£3,052 / week

Book View

from £513 / night

14

Winchester holiday home rental

Hampshire / Winchester

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Child friendly

from £129 / night

£899 / week

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from £129 / night

(1) Excellent 

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 £110 / night

£768 / week

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from £110 / 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 £99 / night

£687 / week

Book View

from £99 / night

(4) Excellent 

21

Holiday home in Winchester

Hampshire / Winchester

3 6 2 nights min

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

from £218 / night

£1,523 / week

Book View

Responds fast!
avg. 1 hour 9 minutes

from £218 / night

(35) Excellent 

Certificate of Excellence

16

Holiday cottage rental

Hampshire / Winchester

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Car not necessary
  • Private garden

Certificate of Excellence

from £166 / night

£1,088 - £1,569 / week

Book View

Responds fast!
avg. 1 hour 30 minutes

from £166 / night

(12) 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 £92 / night

£573 / week

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Responds fast!
avg. 3 hours 30 minutes

from £92 / night

4

Holiday apartment in Winchester

Hampshire / Winchester

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly

from £172 / night

£1,203 / week

Book View

from £172 / 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

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
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
The Old Tractor Barn, Crabwood Cottages
Absolutely lovely cottage in a wonderful setting

This cottage was gorgeous. It was super clean and a lovely cream tea was left for us when we arrived. Debbie is a lovely thoughtful lady. My dog lost her collar and I mentioned to Debbie that I was going to have to find somewhere to get her another. Next thing there were 2 sizes put through the letter box. The setting is amazing. The woods run at the bottom of the garden, and the horses are always looking for treats. I would love to returnsee more
The Granary Annex at Worthy Barn
Do not hesitate to book - The Granary is a Gem!

I have only good things to say about the granary! The décor is beautiful, location is perfect, just opposite a farm shop that do some great bits and have a lovely café! The bed was comfy and the bathroom is stunning! We have a little lad who is 1 year old and Catherine offered to supply a travel cot which meant we saved some valuable boot space! All in all a great place to stay and we will definitely look to stay again in the future.see more
Luxury 2 Bedroom Scandinavian Lodge with HOT TUB
Lovely mini-break

From the moment we walked in the lodge, we were pleased. Fresh flowers on the table,the fire place, the wood beams, it was spacious, well-equipped and clean and tidy. The beds were comfy,shower was good and hot tub was lovely. The Breakfast box was lovely. We booked late so missed out on being able to have afternoon tea (as it's ordered from a bakery, so if you are interested in that please book earlier). The Bluetooth speaker, putting equipment were nice additions to adding something extra. My only slight critism and suggestion; 1) the hairdryer provided in the master room was not particularly that great (I do have long hair and struggled) but lucikly there was a second one provided for the other bedroom which was better. 2) I think providing kitchen roll would also have been handy, as it's not something we thought to buy and is useful in cleaning and tidying up. Going back to the good stuff; We appreciated the information pack which provided lots of handy information for our stay and the team came around to visit once we checked in and again before we left to check everything was okay. Overall, very recommended and we are already talking about when we are going back. Thank you :-)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 amazing with beautiful views and had many nice touches. Couldn't fault it, would definitely stay again! Thank you for a great stay!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

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