Winchester Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Winchester holiday rentals

TV

Aethelred Annexe - New Build with Full Amenities

Aethelred Annexe - New Build with Full Amenities
2.0 star property
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$847
HK$1,015 total
includes taxes & fees
5 Feb - 6 Feb
Aethelred Annexe - New Build with Full Amenities
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$1,695
HK$2,145 total
includes taxes & fees
25 Jan - 26 Jan
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
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$8,212
HK$8,359 total
includes taxes & fees
23 Jan - 24 Jan
Birdsong House
Dining

Squirrel's Leap

Squirrel's Leap
3.0 star property
Winchester
The price is HK$4,286
HK$5,143 total
includes taxes & fees
8 Feb - 9 Feb
Squirrel's Leap
Interior

Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester
Winchester
The price is HK$10,430
HK$10,577 total
includes taxes & fees
23 Jan - 24 Jan
Birdsong Mansion sleeps 12 Twyford Winchester
Interior

Sunday Winchester Wessex Cathedral Hotel | Compact

Sunday Winchester Wessex Cathedral Hotel | Compact
Southampton
The price is HK$698
HK$698 total
includes taxes & fees
29 Jan - 30 Jan
Sunday Winchester Wessex Cathedral Hotel | Compact
Dining

Piping Green 4Bedroom House

Piping Green 4Bedroom House
Colden Common
The price is HK$2,982
HK$3,180 total
includes taxes & fees
2 Feb - 3 Feb
Piping Green 4Bedroom House
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$1,625
HK$2,935 total
includes taxes & fees
29 Jan - 30 Jan
2-BR Cosy Retreat, w/ Garden, central Winchester
4 bedrooms, iron/ironing board, free WiFi

Piping House 4bedroom

Piping House 4bedroom
Colden Common
The price is HK$2,793
HK$2,992 total
includes taxes & fees
23 Jan - 24 Jan
Piping House 4bedroom
1 bedroom, iron/ironing board, WiFi, bed sheets

Garden room, central Winchester

Garden room, central Winchester
Winchester
The price is HK$942
HK$1,109 total
includes taxes & fees
25 Jan - 26 Jan
Garden room, central Winchester
Interior

Sunday Winchester Wessex Cathedral Hotel | Twin

Sunday Winchester Wessex Cathedral Hotel | Twin
Winchester
The price is HK$949
HK$949 total
includes taxes & fees
5 Feb - 6 Feb
Sunday Winchester Wessex Cathedral Hotel | Twin
Property grounds

Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester
The price is HK$7,541
HK$9,049 total
includes taxes & fees
1 Feb - 2 Feb
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$1,778
HK$1,988 total
includes taxes & fees
27 Jan - 28 Jan
Beautiful 4 berth boat on the Isle of Wight for the ultimate relaxation
Balcony

Groomes Country House

Groomes Country House
3.5 star property
Bordon
The price is HK$27,104
HK$32,525 total
includes taxes & fees
26 Jan - 27 Jan
Groomes Country House
Exterior

Bridge Farmhouse

Bridge Farmhouse
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (19 reviews)
"Staying here felt like you walked into a story book; beautiful gardens, bridge over the creek with swans swimming up and down, sheep in the fields, views of Salisbury Cathedral, stylish decorated rooms. We greatly enjoyed our stay. "
Canada
Jennifer E
The price is HK$16,101
HK$19,321 total
includes taxes & fees
30 Jan - 31 Jan
Bridge Farmhouse
Exterior

Bell Cottage

Bell Cottage
Cowes
10.0 out of 10, Exceptional, (8 reviews)
"Anonymous: Accommodation lovely. Owners seem to have thought of everything to make our stay very pleasant. Nicely situated to explore the Island. Enjoyed our stay."
United States
Anonymous traveller
The price is HK$33,477
HK$37,295 total
includes taxes & fees
2 Feb - 3 Feb
Bell Cottage
Interior

Bury Villa - sleeping 18 guests

Bury Villa - sleeping 18 guests
Gosport
9.6 out of 10, Exceptional, (18 reviews)
"Property was exactly how it was listed. Great location, short walk to the ferry to get over to Portsmouth & short drive to the closest beach. "
United Kingdom
Zoe C.
The price is HK$11,505
HK$11,505 total
includes taxes & fees
26 Jan - 27 Jan
Bury Villa - sleeping 18 guests
Interior entrance

room2 Southampton Hometel

room2 Southampton Hometel
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,187 reviews)
"Staff were very helpful. Room is very well maintained and it's a warm feeling through out. "
United Kingdom
Trevor Charles
The price is HK$654
HK$785 total
includes taxes & fees
25 Jan - 26 Jan
room2 Southampton Hometel
Marina

Dairy House - a house that sleeps 16 guests in 7 bedrooms

Dairy House - a house that sleeps 16 guests in 7 bedrooms
Gosport
9.8 out of 10, Exceptional, (30 reviews)
"Lovely well eqipped accommodation which was ideal for our family of 14. Rooms were spacious and there was lots to do including a games room. Good location right near the sea."
United Kingdom
Diane S.
The price is HK$12,611
HK$12,611 total
includes taxes & fees
26 Jan - 27 Jan
Dairy House - a house that sleeps 16 guests in 7 bedrooms
Dining

Grove Lodge - a house that sleeps 13 guests in 5 bedrooms

Grove Lodge - a house that sleeps 13 guests in 5 bedrooms
Gosport
9.6 out of 10, Exceptional, (15 reviews)
"No complaints - everything was very wel organised, clean and nice. Would recommend!"
United States
Johan B.
The price is HK$10,591
HK$10,591 total
includes taxes & fees
2 Feb - 3 Feb
Grove Lodge - a house that sleeps 13 guests in 5 bedrooms
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

10/10 Excellent
"Very clean, lovely staff & delicious food!"
Joanne 1-night trip
Posted 2 days ago
Leonardo Royal Southampton Grand Harbour

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
  • Use the map to find apartments and other holiday homes in the Winchester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winchester while they last

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?

Beautiful 2 bedroom full-furnished semi-detached house with parking : This holiday home rental outside of Winchester has laundry facilities and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and an oven.

How many holiday rentals are there in Winchester?

Expedia has 38 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.