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

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245 Holiday homes

Holiday guest house in Winchester

Winchester guest house

1 bedroom • 1 bathroom • sleeps 2

from £98 / night

£619 - £699 / week

1 / 22

Holiday lodge with golf nearby in Winchester

Winchester lodge

2 bedrooms • 2 bathrooms • sleeps 4

from £141 / night

£842 - £2,359 / week

1 / 21

Winchester holiday apartment let

Winchester apartment

3 bedrooms • 2 bathrooms • sleeps 5

from £178 / night

£1,123 / week

1 / 12

Holiday apartment with golf nearby in Winchester

Winchester apartment

1 bedroom • 1 bathroom • sleeps 4

“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 £121 / night

£682 - £842 / week

1 / 22

Holiday apartment in Winchester

Winchester apartment

2 bedrooms • 1 bathroom • sleeps 5

“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 £120 / night

£135 - £900 / week

1 / 8

Holiday cottage rental

Pitt cottage

3 bedrooms • 2 bathrooms • sleeps 5

from £103 / night

£630 - £994 / week

1 / 31

Home rental in Winchester

Winchester house

2 bedrooms • 2 bathrooms • sleeps 6

from £201 / night

£1,317 - £1,718 / week

1 / 17

Holiday lodge with golf nearby in Winchester

Winchester lodge

3 bedrooms • 2 bathrooms • sleeps 6

from £164 / night

£979 - £2,605 / week

1 / 20

Holiday cottage in Winchester

Winchester cottage

2 bedrooms • 1 bathroom • sleeps 4

from £172 / night

£1,025 / week

1 / 18

Winchester holiday cottage accommodation

Winchester cottage

1 bedroom • 1 bathroom • sleeps 2

from £103 / night

£722 / week

1 / 15

Winchester holiday b&b rental

Winchester b&b

1 bedroom • 1 bathroom • sleeps 2

from £92 / night

£642 / week

1 / 27

Holiday home rental

Winchester house

3 bedrooms • 3 bathrooms • sleeps 6

from £218 / night

£1,523 / week

1 / 17

Holiday log cabin rental

Winchester log cabin

3 bedrooms • 2 bathrooms • sleeps 6

from £141 / night

£842 - £2,376 / week

1 / 20

Studio rental in Winchester with golf nearby

Winchester studio

Studio • 2 bathrooms • sleeps 7

“Excellent Location” The apartment, although billed as a studio, is spacious, clean and modern with everything you need for a pleasant stay. The booking procedure could not have been any simpler. The directions were excellent we were soon parked and unpacked ready to explore. The apartment is ideally situated just above a lovely bay, with amazing views of the sea and literally two mins to the beach. I would recommend the apartment to anyone wanting to get away from it all but have all the amenities close at hand.

from £80 / night

£1,000 - £1,200 / week

1 / 15

Holiday home in Winchester

Winchester house

2 bedrooms • 1 bathroom • sleeps 7

from £213 / night

£1,488 - £1,656 / week

1 / 11

Holiday log cabin rental

Winchester log cabin

2 bedrooms • 2 bathrooms • sleeps 4

from £178 / night

£756 - £2,101 / week

1 / 13

Holiday apartment in Winchester

Winchester apartment

2 bedrooms • 1 bathroom • sleeps 4

from £141 / night

£986 / week

1 / 47

Apartment rental in Winchester

Winchester apartment

1 bedroom • 1 bathroom • sleeps 2

from £144 / night

£802 / week

1 / 13

Holiday home rental

Winchester house

2 bedrooms • 2 bathrooms • sleeps 4

from £149 / night

£938 / week

1 / 15

Holiday log cabin with golf nearby in Winchester

Winchester log cabin

3 bedrooms • 2 bathrooms • sleeps 6

from £110 / night

£768 / week

1 / 12

Holiday log cabin with golf nearby in Winchester

Winchester log cabin

2 bedrooms • 2 bathrooms • sleeps 4

from £99 / night

£687 / week

1 / 14

Holiday home in Winchester

Winchester house

3 bedrooms • 3 bathrooms • sleeps 6

from £218 / night

£1,523 / week

1 / 21

Holiday cottage rental

Winchester cottage

1 bedroom • 1 bathroom • sleeps 3

“Luxurious home away from home” My boyfriend and I stayed here last weekend and had the most wonderful time. We felt very spoiled, especially with the complimentary wine, champagne and chocolates. The steam room and garden area really differentiates it from any where else we've ever been. We would strongly recommend and look forward to going back again soon.

from £166 / night

£1,088 - £1,569 / week

1 / 19

Holiday b&b in Winchester

Winchester b&b

1 bedroom • 1 bathroom • sleeps 2

from £92 / night

£573 / week

1 / 7

Holiday home in Winchester

Winchester house

3 bedrooms • 1 bathroom • sleeps 5

from £172 / night

£1,145 / week

1 / 18

Tented camp rental in Itchen Abbas with golf nearby

Itchen Abbas tented camp

1 bedroom • 1 bathroom • sleeps 4

from £172 / night

£1,203 / week

1 / 16

Holiday cottage in Winchester

Winchester cottage

3 bedrooms • 1 bathroom • sleeps 5

from £121 / night

£796 / week

1 / 33

Holiday tented camp in Itchen Abbas

Itchen Abbas tented camp

1 bedroom • 1 bathroom • sleeps 4

from £172 / night

£1,203 / week

1 / 16

Holiday apartment rental

Winchester apartment

1 bedroom • 1 bathroom • sleeps 4

from £181 / night

£887 / week

1 / 14

Itchen Abbas holiday tented camp accommodation

Itchen Abbas tented camp

1 bedroom • 1 bathroom • sleeps 4

from £172 / night

£1,203 / week

1 / 16

Holiday apartment in Winchester

Winchester apartment

1 bedroom • 1 bathroom • sleeps 2

from £81 / night

£555 - £920 / week

1 / 12

Itchen Abbas holiday tented camp rental

Itchen Abbas tented camp

5 bedrooms • 1 bathroom • sleeps 4

from £172 / night

£1,203 / week

1 / 16

Holiday home in Winchester

Winchester house

3 bedrooms • 1 bathroom • sleeps 5

from £287 / night

£2,004 / week

1 / 53

Apartment rental in Winchester

Winchester apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £161 / night

£916 / week

1 / 22

Great rentals within 20 miles that match your search

Apartment rental in Old Blendworth

Old Blendworth apartment

1 bedroom • 1 bathroom • sleeps 2

Pricing unknown

1 / 18

Holiday cottage with golf nearby in Lyndhurst

Lyndhurst cottage

3 bedrooms • 2 bathrooms • sleeps 6

from £172 / night

£682 - £1,254 / week

1 / 13

Holiday home in Beaulieu

Beaulieu house

6 bedrooms • 7 bathrooms • sleeps 12

from £745 / night

£5,210 / week

1 / 9

Holiday apartment in Southampton

Southampton apartment

1 bedroom • 1 bathroom • sleeps 2

from £75 / night

£521 / week

1 / 15

Holiday cottage in Worcester

Worcester cottage

3 bedrooms • 2 bathrooms • sleeps 4

from £88 / night

£616 / week

1 / 4

Hamble holiday home rental

Hamble house

2 bedrooms • 2 bathrooms • sleeps 4

from £121 / night

£802 / week

1 / 16

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Winchester holidays

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

Meed
Lovely place

We booked this lovely studio for 2 nights and everything was great. The location, the size of the studio and the kitchen is very well equipped. There was a file with all details for heating, TV, kitchen appliances. Lovely view from the balcony. We will definitely come back. … see more
The Down House Cottage
Great stay

Very good place to stay to exore the area . Train station in village is a benefit as did not use car . Cottage has everything you need for a self catering stay . To sit out in the evening and look out at beautiful garden was wonderful … see more
City Centre Apartment Winchester with parking provided
Winchester Apartment

Great apartment, clean . Great location . 3 mins walk to the Centre. 5 mins to station. Would book again . … see more
Hang Your Hat - stylish hideaway in Winchester
Gorgeous little place

We were let down at the last minute by another cottage letting company but Mike answered our request straight away. Hang Your Hat is such a lovely little house with everything you would need. We are very happy things worked out the way they did as we could have not found anywhere better that Hang Your Hat. It was close to all the places on interest, bars and restaurants of Winchester. We would definitely go back and would certainly recommend to others.see more
The Old Tractor Barn, Crabwood Cottages
Lovely cottage, ideal for a family

We had a great 4 night stay at the cottage. It was perfect for a family of 4, or could comfortably house 5. 2 good sized double bedrooms and one single. Plenty of storage and lots of home comforts supplied. Lovely garden and surrounded by open spaces and countryside. We visited Peppa pig world, Bournemouth and Winchester from here.see more
Luxury 2 Bedroom Scandinavian Lodge with HOT TUB
Throughly enjoyed our stay

We had the best time in our log cabin. Clean, all the facilities were fantastic and we would highly recommend to anyone and we already have. … see more

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