Winchester Vacation 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
May 8 - May 10
In two months
Jun 19 - Jun 21
In three months
Jul 17 - Jul 19
In four months
Aug 14 - Aug 16

Our top choices for Winchester vacation 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 ￥29,020
￥38,693 total
includes taxes & fees
Apr 23 - Apr 24
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
Double Room

Settle Winchester

Settle Winchester
2.0 star property
Winchester
The price is ￥7,928
￥25,657 total
includes taxes & fees
May 4 - May 5
Settle Winchester
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 ￥168,744
￥171,753 total
includes taxes & fees
Apr 23 - Apr 24
Birdsong House
Interior

Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester
Winchester
The price is ￥214,316
￥217,325 total
includes taxes & fees
Apr 23 - Apr 24
Birdsong Mansion sleeps 12 Twyford Winchester
Iron/ironing board, travel crib, WiFi, bed sheets

Winchester City Centre Flat/Sleeps 6/Free Parking

Winchester City Centre Flat/Sleeps 6/Free Parking
Hampshire
The price is ￥24,325
￥43,671 total
includes taxes & fees
Apr 26 - Apr 27
Winchester City Centre Flat/Sleeps 6/Free Parking
4 bedrooms, iron/ironing board, free WiFi

Piping House 4bedroom

Piping House 4bedroom
Colden Common
The price is ￥57,395
￥61,479 total
includes taxes & fees
Apr 23 - Apr 24
Piping House 4bedroom
Dining

Squirrel's Leap

Squirrel's Leap
3.0 star property
Winchester
The price is ￥88,069
￥105,683 total
includes taxes & fees
May 8 - May 9
Squirrel's Leap
1 bedroom, iron/ironing board, WiFi, bed sheets

Garden room, central Winchester

Garden room, central Winchester
Winchester
The price is ￥19,346
￥22,785 total
includes taxes & fees
Apr 24 - Apr 25
Garden room, central Winchester
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 ￥17,412
￥20,851 total
includes taxes & fees
Apr 26 - Apr 27
Aethelred Annexe - New Build with Full Amenities
Interior

Sunday Winchester Wessex Cathedral Hotel | Compact

Sunday Winchester Wessex Cathedral Hotel | Compact
Southampton
The price is ￥9,654
￥9,654 total
includes taxes & fees
May 10 - May 11
Sunday Winchester Wessex Cathedral Hotel | Compact
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 ￥18,065
￥18,065 total
includes taxes & fees
Apr 26 - Apr 27
Sunday Winchester Wessex Cathedral Hotel | Classic
Interior

Sunday Winchester Wessex Cathedral Hotel | Twin

Sunday Winchester Wessex Cathedral Hotel | Twin
Winchester
6.0 out of 10, (1 review)
"Didn’t have Kitchen like advertised, no fridge unfortunately "
United Kingdom
Hayden
The price is ￥14,670
￥14,670 total
includes taxes & fees
May 5 - May 6
Sunday Winchester Wessex Cathedral Hotel | Twin
Property grounds

Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester
The price is ￥154,944
￥185,933 total
includes taxes & fees
Apr 29 - Apr 30
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 ￥36,543
￥41,702 total
includes taxes & fees
Apr 23 - Apr 24
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 ￥13,703
￥16,444 total
includes taxes & fees
Apr 23 - Apr 24
Hollington Park Glamping
Marina

Y Knot - The New Way To Holiday

Y Knot - The New Way To Holiday
Lymington
9.4 out of 10, Exceptional, (3 reviews)
"Agent failed to mention that the toilet was not to be used for number "two s" ."
United Kingdom
manojkunar P.
The price is ￥59,114
￥65,993 total
includes taxes & fees
Apr 30 - May 1
Y Knot - The New Way To Holiday
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 traveler
The price is ￥185,726
￥216,121 total
includes taxes & fees
Apr 23 - Apr 24
York Street
Bell Tent

Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
7.0 out of 10, Good, (2 reviews)
"The shepherds hut I stayed in for one night was so warm and cosy, it was like staying in a giant wendy house. I would have liked face to face contact with the host, but I guess thats a "sign of the times" Beautiful view of the countryside. "
United Kingdom
Deby
The price is ￥13,567
￥16,281 total
includes taxes & fees
Apr 26 - Apr 27
Stone Circle Glamping
Exterior

Cosy Rural Cabin With Ensuite without Pergola

Cosy Rural Cabin With Ensuite without Pergola
Chawton
10.0 out of 10, Exceptional, (7 reviews)
"Brilliant location , helpful staff , nice place for the kids to have a run around and make friends "
United Kingdom
Jay S.
The price is ￥21,281
￥21,281 total
includes taxes & fees
Apr 27 - Apr 28
Cosy Rural Cabin With Ensuite without Pergola
Deluxe Studio Suite, Garden View | Iron/ironing board, free WiFi

Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking

Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
2.0 star property
Gosport
The price is ￥12,288
￥14,746 total
includes taxes & fees
Apr 29 - Apr 30
Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
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

voco Southampton by IHG

voco Southampton by IHG

8/10 Good
"Low choices continental breakfast; basic Fitness room"
Pedro 1-night trip
Posted 2 hours ago
voco Southampton by IHG

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 vacation rentals in Winchester?

Yes, we give you a choice of vacation rentals in Winchester close to Winchester Science Centre and Planetarium, or you can go with 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 vacation home rentals in Winchester?

Birdsong Mansion sleeps 12 Twyford Winchester: Visitors give good reviews to this Winchester vacation home rental, which offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Winchester?

Expedia has 44 vacation 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 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 like Southampton Cruise Terminal and New Forest National Park.

What’s a vacation rental in Winchester like?

A vacation rental is a private property where you can stay for several days or longer in Winchester. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular choice for a family getaway.