Winchester Holiday Rentals

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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Winchester holiday rentals

Terrace/patio

Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Winchester
9.0 out of 10, Wonderful, (4 reviews)
"Lovely cabin and outside kitchen plus garden. It's my second stay and I enjoyed my stay. Love the garden kitchen,. It's very pretty and relaxing ."
United Kingdom
Nicola H.
The price is HK$1,397
HK$1,894 total
includes taxes & fees
6 Apr - 7 Apr
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
4 bedrooms, iron/ironing board, free WiFi

Piping House 4bedroom

Piping House 4bedroom
Colden Common
The price is HK$2,763
HK$2,960 total
includes taxes & fees
6 Apr - 7 Apr
Piping House 4bedroom
Fridge, microwave, oven, stovetop

2-BR Cosy Retreat, w/ Garden, central Winchester

2-BR Cosy Retreat, w/ Garden, central Winchester
Winchester
8.0 out of 10, Very good, (2 reviews)
"The property was excellent for location in Winchester and was very clean. The ‘garden’ is a small area of decking. "
United Kingdom
barbara
The price is HK$1,449
HK$2,742 total
includes taxes & fees
6 Apr - 7 Apr
2-BR Cosy Retreat, w/ Garden, central Winchester
Iron/ironing board, travel cot, WiFi, bed sheets

Winchester City Centre Flat/Sleeps 6/Free Parking

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
The price is HK$981
HK$1,912 total
includes taxes & fees
6 Apr - 7 Apr
Winchester City Centre Flat/Sleeps 6/Free Parking
1 bedroom, iron/ironing board, WiFi, bed sheets

Garden room, central Winchester

Garden room, central Winchester
Winchester
The price is HK$931
HK$1,097 total
includes taxes & fees
11 Apr - 12 Apr
Garden room, central Winchester
Dining

Squirrel's Leap

Squirrel's Leap
3.0 star property
Winchester
The price is HK$4,240
HK$5,087 total
includes taxes & fees
11 Apr - 12 Apr
Squirrel's Leap
TV

Escape to Boscobel: Enjoy a Cosy 1 Bed Apartment with Free Parking

Escape to Boscobel: Enjoy a Cosy 1 Bed Apartment with Free Parking
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"This apartment was exactly what we wanted, it was well equipped as we cooked an evening meal and breakfast while there. The host was very accommodating, easy check in and instructions were clear, cannot fault this apartment in any way, the pillows and bedding were exceptional quality."
United Kingdom
Karen J.
The price is HK$1,055
HK$1,418 total
includes taxes & fees
6 Apr - 7 Apr
Escape to Boscobel: Enjoy a Cosy 1 Bed Apartment with Free Parking
1 bedroom

Aethelred Annexe - New Build with Full Amenities

Aethelred Annexe - New Build with Full Amenities
Winchester
10.0 out of 10, Exceptional, (1 review)
"Had a lovely stay at the Aethelred Annexe! Great amenities and an incredibly generous host. It felt very warm and cozy and the bed was super comfy. Great location for a quick drive/ bus into the city centre. Would absolutely recommend."
United States
Andrea W.
The price is HK$838
HK$1,004 total
includes taxes & fees
9 Apr - 10 Apr
Aethelred Annexe - New Build with Full Amenities
Interior

Birdsong House

Birdsong House
Winchester
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at Birdsong house. The owner was always available and the house was so cozy and comfortable! Thank you"
United Kingdom
Judith D.
The price is HK$8,123
HK$8,268 total
includes taxes & fees
6 Apr - 7 Apr
Birdsong House
Interior

Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester
Winchester
The price is HK$10,317
HK$10,462 total
includes taxes & fees
6 Apr - 7 Apr
Birdsong Mansion sleeps 12 Twyford Winchester
Interior

Sunday Winchester Wessex Cathedral Hotel | Classic

Sunday Winchester Wessex Cathedral Hotel | Classic
Winchester
6.0 out of 10, (1 review)
"Carpets and sofa in room were noticeably stained. Otherwise the view was great, bed was comfortable and clean. Staff were very helpful and professional "
Canada
Cathy
The price is HK$944
HK$944 total
includes taxes & fees
26 Apr - 27 Apr
Sunday Winchester Wessex Cathedral Hotel | Classic
Property grounds

Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester
The price is HK$7,459
HK$8,951 total
includes taxes & fees
11 Apr - 12 Apr
Rivergem - Riverside Coach House
Spa

Beautiful 4 berth boat on the Isle of Wight for the ultimate relaxation

Beautiful 4 berth boat on the Isle of Wight for the ultimate relaxation
Binfield
10.0 out of 10, Exceptional, (1 review)
"Best stay! Very new experience of staying in a boat. Amazing location for public services as well. "
United Kingdom
srini k.
The price is HK$1,759
HK$2,008 total
includes taxes & fees
6 Apr - 7 Apr
Beautiful 4 berth boat on the Isle of Wight for the ultimate relaxation
Exterior

Hollington Park Glamping

Hollington Park Glamping
2.0 star property
Newbury
8.0 out of 10, Very good, (2 reviews)
"We had a lovely time here with our 2 year old for two nights. We stayed in the Bluebell Pod which was so cosy and comfortable. We had everything we needed and really enjoyed the woods and the animals. Many thanks. Hope to come again next year! "
United Kingdom
maria
The price is HK$620
HK$744 total
includes taxes & fees
16 Apr - 17 Apr
Hollington Park Glamping
Terrace/patio

Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool

Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool
Chandler's Ford
The price is HK$661
HK$982 total
includes taxes & fees
13 Apr - 14 Apr
Romantic Swiss Cabin Hideaway & Hot Tub Spa Pool
Free WiFi

Pebbles Guest House - Flat 7

Pebbles Guest House - Flat 7
2.0 star property
Freemantle
The price is HK$517
HK$621 total
includes taxes & fees
6 Apr - 7 Apr
Pebbles Guest House - Flat 7
Free WiFi

The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
The price is HK$891
HK$1,380 total
includes taxes & fees
6 Apr - 7 Apr
The Riley Stable- Cozy Getaway
TV

York Street

York Street
Cowes
10.0 out of 10, Exceptional, (8 reviews)
"It was absolutely perfect ! The house was so well looked after ."
United States
Anonymous traveller
The price is HK$8,941
HK$10,404 total
includes taxes & fees
7 Apr - 8 Apr
York Street
Outdoor dining

Beautiful New Forest Hideaway

Beautiful New Forest Hideaway
West Wellow
The price is HK$993
HK$1,511 total
includes taxes & fees
27 Apr - 28 Apr
Beautiful New Forest Hideaway
Iron/ironing board, free WiFi

Studio 24

Studio 24
2.0 star property
Southsea
The price is HK$973
HK$973 total
includes taxes & fees
7 Apr - 8 Apr
Studio 24
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winchester Hotel Reviews

Winchester Royal Hotel

Winchester Royal Hotel

4/10 Poor
"Bed wasn’t comfortable. Pillows rock hard. Rooms very hot and small. They did however move us a slightly bigger room. 1:30am people in corridor shouting and laughing. There is a clear gap in the front door and corridor seen at the bottom. Talking about a good half inch. 3am wedding party in the gardens shouting and again very loud. Tried to call reception to alert and ask to quiet down as 3-4people shouting in the garden. No answer. Impossible to get through to reception. On check out I explained this and no care what so ever but proceeded to take the card machine out and say you owe us £10. "
Vishnu 2-night trip
Posted 2 hours ago
Winchester Royal Hotel

Find out more about Winchester

Search for holiday rentals in Winchester on Expedia! You can easily find your home rentals, villas, holiday apartments in Winchester using one of the methods below:

  • View our selection of featured holiday rentals in Winchester
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Look no further and take a look at our great range of rental properties in Winchester!

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Winchester Science Centre and Planetarium, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the stunning cathedral and picturesque gardens in Winchester. The array of shops and festivals are some other things you might want to check out while you're here.

What are some of the best holiday rentals that Winchester has to offer?

Birdsong Mansion sleeps 12 Twyford Winchester: This highly rated holiday home rental in Winchester offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Make the most of garden in this rental home to help you unwind.

How many holiday rentals are there in Winchester?

Expedia has 42 holiday rentals for your stay in Winchester.

What’s there to see and do in Winchester?

Winchester Science Centre and Planetarium and Marwell Zoo are a couple of the family-friendly sights, whereas cultural attractions include Great Hall and Horsepower The Museum Of The King's Royal Hussars. While in the area, you can also visit popular places such as Southampton Cruise Terminal and New Forest National Park.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.