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

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327 Holiday homes

(5) Very Good 

41

Pet friendly accommodation in Winchester with satellite tv, sleeps 2, horse riding

Hampshire / Winchester

1 2 2 nights min

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

from £125 / night

£850 / week

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from £125 / night

(3) Very Good 

21

Looking for pet friendly accommodation in Winchester? Rent this lodge from £143/night

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

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from £143 / night

(7) Very Good 

17

House in Winchester with bicycles available from £175/night - Perfect for fishing, cycling holidays & city breaks

Hampshire / Winchester

2 6 5 nights min

  • 2 bedrooms
  • sleeps 6
  • 5 nights min
  • Child friendly
  • Car not necessary

from £175 / night

£1,150 - £1,500 / week

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from £175 / night

(6) Very Good 

11

3 bedroom accommodation in Winchester

Hampshire / Winchester

3 5 2 nights min

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

from £155 / night

£980 / week

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from £155 / night

(20) Excellent 

Certificate of Excellence

27

Certificate of Excellence cottage in Pitt with table tennis and bbq - golf within 30mins drive

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 - £840 / week

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Responds fast!
avg. 2 hours 8 minutes

from £120 / night

(19) Excellent 

16

Escape to Winchester, Hampshire in this beautiful holiday penthouse | Sleeps 6, 2 bedrooms

Hampshire / Winchester

2 6 2 nights min

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

from £200 / night

£1,000 - £1,100 / week

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Responds fast!
avg. 2 hours 38 minutes

from £200 / night

(8) Excellent 

17

Holiday rental in Winchester from £190/night. Sleeps 6, 3 bedrooms

Hampshire / Winchester

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary

from £190 / night

£1,330 / week

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Responds fast!
avg. 1 hour 48 minutes

from £190 / night

(24) Excellent 

8

Spacious self catering property in Winchester | sleeps 8 | pet friendly, city breaks

Hampshire / Winchester

3 8 2 nights min

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

from £335 / night

£2,345 / week

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from £335 / night

(9) Excellent 

15

Cosy rental in Winchester, Hampshire, sleeps 2 | wi-fi

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 £90 / night

£630 / week

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from £90 / night

(10) Excellent 

17

Top rated holiday guest house in Winchester | city breaks | Sleeps 2 | golf within 30mins drive | Nearest beach 25 km

Hampshire / Winchester

1 2 min stay varies

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

from £100 / night

£560 - £630 / week

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Responds fast!
avg. 2 hours 8 minutes

from £100 / night

7

Holiday house in Winchester, Hampshire, from £700/night. With bbq, swimming pool and much more!

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

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Responds fast!
avg. 1 hour 58 minutes

from £700 / night

(11) Very Good 

18

Stay at this cottage in Winchester with bbq, garden & wi-fi from £150/night

Hampshire / Winchester

2 4 4 nights min

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

from £150 / night

£895 / week

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from £150 / night

(13) Excellent 

Certificate of Excellence

18

Log cabin in Winchester that has earned great reviews from travellers from £60/night - Perfect for walking holidays

Hampshire / Winchester

1 2 2 nights min

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

Certificate of Excellence

from £60 / night

£350 / week

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Responds fast!
avg. 3 hours 59 minutes

from £60 / night

(9) Excellent 

20

Authentic log cabin in Winchester, Hampshire | tennis in town | Nearest beach 20 km

Hampshire / Winchester

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 20 km
  • Child friendly
  • Pet friendly

from £123 / night

£735 - £1,335 / week

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from £123 / night

(29) Excellent 

8

Fantastic rental in Winchester, Hampshire - Great for cycling holidays and walking holidays | wi-fi

Hampshire / Winchester

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
“Super little apartment” The whole experience was great with prompt and friendly response from the owner. The apartment is fully detached above the car parking area with a small balcony to the living room. The kitchen is very well equipped with dish washer and washing machine. There was a good size flat screen TV in the lounge with comfortable seating. There is a double bed room and the second bedroom sleeps 3 in a bunk. Everything was exactly as in the photographs on the booking site. It is located in a quiet cul-de-sac about 1 mile from the centre of Winchester. Although close to the railway line, the double glazing makes the trains hardly noticeable. I would definitely book this again if I was visiting Winchester.

from £110 / night

£725 - £810 / week

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from £110 / night

(1) Excellent 

21

Child friendly rental - 2 bedrooms in Winchester, Hampshire with golf course on site / within 15 min walk

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

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from £123 / night

(10) Excellent 

9

Private b&b with 1 bedroom in Winchester | balcony / terrace, patio and more

Hampshire / Winchester

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £65 / night

£455 / week

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Responds fast!
avg. 2 hours 58 minutes

from £65 / night

7

2 bedroom house in Winchester from £147/night | patio & fireplace

Hampshire / Winchester

2 5 7 nights min

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

from £148 / night

£1,031 - £1,080 / week

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from £148 / night

(8) Excellent 

15

Self-catering apartment in Winchester with satellite tv & solarium / roof terrace - Great for city breaks

Hampshire / Winchester

1 2 2 nights min

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

from £90 / night

£560 - £635 / week

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from £90 / night

29

Comfortable townhouse in Hampshire. Sleeps 6 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

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from £169 / night

(16) Very Good 

16

Holiday rental in Winchester with nightlife, cycling holidays

Hampshire / Winchester

1 4 5 nights min

  • 1 bedroom
  • sleeps 4
  • 5 nights min
  • Child friendly
  • Car not necessary
“Great place to stay in Wichester” The apartment was exactly as described and worked well for our party of 3 adults. Everything was in good order & the main bedroom very spacious with doors onto the small courtyard. An added bonus was the private parking which is very hard to find in this city! Location was fantastic - only a 5 minute walk to town center and even less to the park at bottom of road. Caroline was a perfect host and met us upon arrival and was always available to contact with any enquiries. All in all very enjoyable.

from £110 / night

£625 - £765 / week

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from £110 / night

(10) Very Good 

14

Holiday accommodation in Winchester with great reviews | satellite tv, wi-fi | golf within 30mins drive

Hampshire / Winchester

2 4 2 nights min

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

from £102 / night

£714 / week

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from £102 / night

17

Apartment in Winchester with fishing - from £159/night

Hampshire / Winchester

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min

from £159 / night

£1,112 - £1,210 / week

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from £159 / night

47

Apartment with 2 bedrooms in Winchester, Hampshire | tennis in town, city breaks & water sports

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

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from £123 / night

(8) Excellent 

13

Log cabin with fireplace, bicycles available, balcony / terrace & more 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 £155 / night

£660 - £1,185 / week

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from £155 / night

14

Enjoy water sports and horse riding in Winchester at this log cabin from £86/night

Hampshire / Winchester

2 4 28 nights min

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

from £86 / night

£600 / week

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from £86 / night

11

House in Winchester with fireplace from £186/night - Great for walking holidays

Hampshire / Winchester

2 7 7 nights min

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

from £186 / night

£1,299 - £1,446 / week

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from £186 / night

(1) Excellent 

12

Beautiful log cabin in idyllic Winchester, Hampshire | sleeps 6

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

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from £96 / night

13

Apartment in Winchester from £125/night | 1 bedroom, sleeps 2

Hampshire / Winchester

1 2 3 nights min

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

from £125 / night

£700 / week

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from £125 / night

(35) Excellent 

Certificate of Excellence

16

Amazing cottage in Winchester from £145/night | wi-fi, satellite tv & garden

Hampshire / Winchester

1 3 2 nights min

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

Certificate of Excellence

from £145 / night

£950 - £1,370 / week

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Responds fast!
avg. 3 hours 7 minutes

from £145 / night

(4) Excellent 

21

House in Winchester with wi-fi | golf within 30mins drive, city breaks & tennis in town | From £190/night

Hampshire / Winchester

3 6 2 nights min

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

from £190 / night

£1,330 / week

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Responds fast!
avg. 1 hour 22 minutes

from £190 / night

(10) Very Good 

11

Winchester - b&b with a very good review rating | wi-fi & garden | city breaks

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

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Responds fast!
avg. 3 hours 47 minutes

from £80 / night

11

Affordable apartment rental in Hampshire – 2 bedrooms from £46/night

Hampshire / Winchester

2 4 min stay varies

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

from £46 / night

£323 - £1,085 / week

Enquire View

from £46 / night

(2) Very Good 

7

Child friendly apartment in Winchester, Hampshire - 1 bedroom | horse riding

Hampshire / Winchester

1 2 2 nights min

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

from £90 / night

£500 / week

Book View

Responds fast!
avg. 2 hours 15 minutes

from £90 / night

12

Experience a home from home at this house in Winchester | fireplace & garden

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

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