Winchester Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Winchester vacation rentals

Iron/ironing board, free WiFi

Settle Winchester

Settle Winchester
2.0 star property
Winchester
The price is ￥7,675
￥25,215 total
includes taxes & fees
Jun 7 - Jun 8
Settle Winchester
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 ￥34,572
￥45,669 total
includes taxes & fees
May 18 - May 19
Cosy A-Frame cabin nestled in the chalk steams of Hampshire
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 ￥17,286
￥20,700 total
includes taxes & fees
May 14 - May 15
Aethelred Annexe - New Build with Full Amenities
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 ￥20,700
￥39,906 total
includes taxes & fees
May 14 - May 15
Winchester City Centre Flat/Sleeps 6/Free Parking
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 ￥167,523
￥170,511 total
includes taxes & fees
May 14 - May 15
Birdsong House
Interior

Birdsong Mansion sleeps 12 Twyford Winchester

Birdsong Mansion sleeps 12 Twyford Winchester
Winchester
The price is ￥212,765
￥215,753 total
includes taxes & fees
May 14 - May 15
Birdsong Mansion sleeps 12 Twyford Winchester
4 bedrooms, iron/ironing board, free WiFi

Piping House 4bedroom

Piping House 4bedroom
Colden Common
The price is ￥56,979
￥61,034 total
includes taxes & fees
May 19 - May 20
Piping House 4bedroom
1 bedroom, iron/ironing board, WiFi, bed sheets

Garden room, central Winchester

Garden room, central Winchester
Winchester
The price is ￥21,341
￥24,755 total
includes taxes & fees
May 18 - May 19
Garden room, central Winchester
Property grounds

Rivergem - Riverside Coach House

Rivergem - Riverside Coach House
2.0 star property
Winchester
The price is ￥153,823
￥184,588 total
includes taxes & fees
Jun 4 - Jun 5
Rivergem - Riverside Coach House
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 ￥36,954
￥36,954 total
includes taxes & fees
May 25 - May 26
Sunday Winchester Wessex Cathedral Hotel | Twin
Dining

Squirrel's Leap

Squirrel's Leap
3.0 star property
Winchester
The price is ￥87,432
￥104,918 total
includes taxes & fees
May 23 - May 24
Squirrel's Leap
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 ￥36,279
￥41,614 total
includes taxes & fees
May 14 - May 15
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 ￥12,992
￥15,591 total
includes taxes & fees
May 20 - May 21
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 ￥58,687
￥67,863 total
includes taxes & fees
May 24 - May 25
Y Knot - The New Way To Holiday
Tent, Courtyard View (Bell Tent )

Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
8.0 out of 10, Very Good, (3 reviews)
"A great location to explore the area, including walking distance to WoodHenge, a short drive to Stonehenge and an hour from Glastonbury. Very quiet, peaceful and quaint. The perfect short break away."
United Kingdom
Iris
The price is ￥9,284
￥11,140 total
includes taxes & fees
May 17 - May 18
Stone Circle Glamping
Front of property

The Hugo Stable- Cozy get away

The Hugo Stable- Cozy get away
2.0 star property
Waterlooville
The price is ￥13,077
￥22,095 total
includes taxes & fees
Jun 5 - Jun 6
The Hugo Stable- Cozy get away
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
9.0 out of 10, Wonderful, (2 reviews)
"Room is well equipped "
United Kingdom
Chris
The price is ￥12,075
￥14,490 total
includes taxes & fees
May 14 - May 15
Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
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 ￥22,194
￥22,194 total
includes taxes & fees
May 14 - May 15
Cosy Rural Cabin With Ensuite without Pergola
Apartment, 1 Bedroom, Patio, Garden View | Living area | 42-inch Smart TV with digital channels, Netflix, streaming services

Rudley Ranch

Rudley Ranch
2.5 star property
Waterlooville
9.0 out of 10, Wonderful, (2 reviews)
"Brilliant stay an highly recommend "
United Kingdom
Damian
The price is ￥15,337
￥24,806 total
includes taxes & fees
May 27 - May 28
Rudley Ranch
1 bedroom, iron/ironing board, WiFi, bed sheets

Portsmouth Gem: King Room Close to Beach

Portsmouth Gem: King Room Close to Beach
Southsea
The price is ￥9,817
￥9,817 total
includes taxes & fees
May 14 - May 15
Portsmouth Gem: King Room Close to Beach
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

Leonardo Royal Southampton Grand Harbour

Leonardo Royal Southampton Grand Harbour

10/10 Excellent
"Great stay, great location"
michael 1-night trip
Posted 3 hours 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:

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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.