Winchester Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Winchester vacation rentals

Interior
Aethelred Annexe - New Build with Full Amenities

Apartment in Winchester

Aethelred Annexe - New Build with Full Amenities
2.0 star property
10.0 out of 10, Exceptional, (1)
"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 ￥15,215
￥18,596 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Aethelred Annexe - New Build with Full Amenities
Dining
Squirrel's Leap

Cottage in Winchester

Squirrel's Leap
3.0 star property
The price is ￥84,424
￥101,309 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Squirrel's Leap
2 bedrooms, WiFi, bed sheets
Cosy A-Frame cabin nestled in the chalk steams of Hampshire

Cabin in Winchester

Cosy A-Frame cabin nestled in the chalk steams of Hampshire
9.4 out of 10, Exceptional, (3)
"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 ￥34,164
￥45,130 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
House (3 Bedrooms) | Terrace/patio
Peaceful Elevated Residential Area - Walk to City

Cottage in Winchester

Peaceful Elevated Residential Area - Walk to City
5.0 star property
The price is ￥56,177
￥67,412 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Peaceful Elevated Residential Area - Walk to City
Interior
Birdsong House

Vacation Home in Winchester

Birdsong House
10.0 out of 10, Exceptional, (1)
"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 ￥165,889
￥168,848 total
includes taxes & fees
Dec 28 - Dec 29
Birdsong House
Private kitchen
Beautiful Hampshire at Mulberry Barn Annexe

Vacation Home in Micheldever

Beautiful Hampshire at Mulberry Barn Annexe
2.0 star property
The price is ￥22,147
￥32,291 total
includes taxes & fees
Dec 28 - Dec 29
Beautiful Hampshire at Mulberry Barn Annexe
Interior
Sunday Winchester Wessex Cathedral Hotel | Compact

Apartment in Southampton

Sunday Winchester Wessex Cathedral Hotel | Compact
The price is ￥15,710
￥15,710 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Sunday Winchester Wessex Cathedral Hotel | Compact
Interior
Birdsong Mansion sleeps 12 Twyford Winchester

Vacation Home in Winchester

Birdsong Mansion sleeps 12 Twyford Winchester
The price is ￥210,690
￥213,649 total
includes taxes & fees
Dec 28 - Dec 29
Birdsong Mansion sleeps 12 Twyford Winchester
1 bedroom, iron/ironing board, WiFi, bed sheets
Garden room, central Winchester

Apartment in Winchester

Garden room, central Winchester
The price is ￥18,980
￥22,354 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Garden room, central Winchester
Smart TV
Piping House 4bedroom

Vacation Home in Colden Common

Piping House 4bedroom
The price is ￥56,424
￥60,439 total
includes taxes & fees
Dec 28 - Dec 29
Piping House 4bedroom
Private kitchen
Piping Green 4Bedroom House

Vacation Home in Colden Common

Piping Green 4Bedroom House
The price is ￥60,227
￥64,242 total
includes taxes & fees
Dec 28 - Dec 29
Piping Green 4Bedroom House
Property grounds
Rivergem - Riverside Coach House

Cottage in Winchester

Rivergem - Riverside Coach House
2.0 star property
The price is ￥152,007
￥182,408 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Rivergem - Riverside Coach House
Interior
Sunday Winchester Wessex Cathedral Hotel | Twin

Apartment in Winchester

Sunday Winchester Wessex Cathedral Hotel | Twin
The price is ￥20,143
￥20,143 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Sunday Winchester Wessex Cathedral Hotel | Twin
Interior
Sunday Winchester Wessex Cathedral Hotel | Classic

Apartment in Winchester

Sunday Winchester Wessex Cathedral Hotel | Classic
6.0 out of 10, (1)
"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 ￥17,863
￥17,863 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Sunday Winchester Wessex Cathedral Hotel | Classic
Marina
Beautiful 4 Berth Boat on the Isle of Wight for the Ultimate Relaxation

Houseboat in Binfield

Beautiful 4 Berth Boat on the Isle of Wight for the Ultimate Relaxation
10.0 out of 10, Exceptional, (1)
"Best stay! Very new experience of staying in a boat. Amazing location for public services as well. "
United Kingdom
srini k.
The price is ￥35,851
￥40,912 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Beautiful 4 Berth Boat on the Isle of Wight for the Ultimate Relaxation
Marina
40 foot luxury yacht on 5* Ocean Village Marina

Houseboat in Southampton City Centre

40 foot luxury yacht on 5* Ocean Village Marina
10.0 out of 10, Exceptional, (2)
"We decided to try something new instead of hotel so booked the yacht. Great experience. Marina and boat were lovely. Lots of restaurants and easy to walk around and explore. Steve and Miros went over and above to make sure our stay was great and even picked us up from cruise port and drove us to airport hotel the next day. Would highly recommend . "
Canada
Sheila
The price is ￥31,487
￥44,378 total
includes taxes & fees
Dec 28 - Dec 29
40 foot luxury yacht on 5* Ocean Village Marina
Property grounds
Cosy Bluebelle Glamping pod in a secluded woodland clearing

Camping in Newbury

Cosy Bluebelle Glamping pod in a secluded woodland clearing
Cosy Bluebelle Glamping pod in a secluded woodland clearing
Luxury Suite, Ensuite | Private kitchen
Stonehenge Cottages

Cottage in Salisbury

Stonehenge Cottages
5.0 star property
9.8 out of 10, Exceptional, (105)
"Information, including a video, provided by the friendly owners before and during our stay was excellent. The beautifully appointed cottage was convenient for Salisbury and for the nearby pub which serves good food. We will definitely stay there again, if in the area."
United Kingdom
Fiona
The price is ￥33,215
￥39,858 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Stonehenge Cottages
Front of property
room2 Southampton Hometel

Aparthotel in Southampton City Centre

room2 Southampton Hometel
4.0 star property
9.4 out of 10, Exceptional, (1179)
"Staff was great and the room was really nice. I was impressed by the design and it was spacious "
United States
Vanessa
The price is ￥13,216
￥15,860 total
includes taxes & fees
Dec 30 - Dec 31
room2 Southampton Hometel
Cottage | Balcony
Groomes Country House

Cottage in Bordon

Groomes Country House
3.5 star property
The price is ￥530,231
￥636,277 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Groomes Country House
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

Moxy Southampton

Moxy Southampton

10/10 Excellent
"Fabulous rooms, fabulous service, convenient and great it welcomes dogs too. "
Maria 2-night trip
Posted 22 hours ago
Moxy Southampton

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 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?

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

How many vacation rentals are there in Winchester?

Expedia has 40 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 Theatre Royal Winchester. 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.