A large red brick building with a central entrance flanked by columns, a fountain in front, and trees on either side.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winchester holiday rentals

A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

1. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is ฿1,298
฿3,954 total
includes taxes & fees
8 Nov - 9 Nov
Settle Winchester
A modern interior with a red sofa, black chairs, and a patterned floor.

2. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,354 reviews)
"Great location and friendly staff!"
United States
Gary
The price is ฿2,921
฿3,506 total
includes taxes & fees
8 Nov - 9 Nov
Second Nature Southampton
A room with a dartboard, a power outlet, a potted plant, and a curtain.

3. 4 Bedrooms - The Family Haven With Parking Near Airport

4 Bedrooms - The Family Haven With Parking Near Airport
3.0 star property
Eastleigh
The price is ฿6,380
฿7,656 total
includes taxes & fees
1 Nov - 2 Nov
4 Bedrooms - The Family Haven With Parking Near Airport
A bedroom with a large bed, a wooden ceiling, and a view of a brick building outside.

4. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.0 out of 10, Very good, (12 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is ฿2,330
฿4,792 total
includes taxes & fees
13 Oct - 14 Oct
Settle Southampton
A bedroom with a bed, a TV, and a window with curtains.

5. Bayview Apartments

Bayview Apartments
2.0 star property
Southampton City Centre
7.8 out of 10, Good, (7 reviews)
"The apartment was reasonably priced, conveniently located to our destination and perfectly adequate for our needs."
United States
Donald
The price is ฿10,354
฿12,425 total
includes taxes & fees
18 Oct - 19 Oct
Bayview Apartments
A tent with a bed inside, a colorful rug, and a sign on the ground.

6. Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
8.8 out of 10, Excellent, (16 reviews)
"Cozy place to stay, it is near a road but it didn’t bother me. It is as advertised"
Canada
Darnell
The price is ฿1,622
฿1,947 total
includes taxes & fees
12 Oct - 13 Oct
Stone Circle Glamping
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

7. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.8 out of 10, (17 reviews)
"They sent me an email at the last minute saying that it was double booked and they canceled my reservation that was already prepaid"
United States
kia
The price is ฿6,110
฿7,333 total
includes taxes & fees
12 Oct - 13 Oct
QE2 Loft Apartments
A bedroom with a bed, a bedside table with a lamp, a window with curtains, a mirror, and a wooden door with a metal handle.

8. Horseshoe Cottage

Horseshoe Cottage
3.0 star property
Romsey
10.0 out of 10, Exceptional, (1 review)
"Well presented and well equipped home. All the essentials plus more. Very family friendly."
United Kingdom
Peter
The price is ฿25,347
฿30,417 total
includes taxes & fees
16 Oct - 17 Oct
Horseshoe Cottage
A corner room with a large window overlooking a city street and buildings.

9. Ocean Quay Luxury - Stylish 2 Bed - Has Parking

Ocean Quay Luxury - Stylish 2 Bed - Has Parking
3.0 star property
Southampton City Centre
The price is ฿5,238
฿6,285 total
includes taxes & fees
13 Oct - 14 Oct
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

10. Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (327 reviews)
"Great. They have everything you could need - well appointed kitchen, milk and breakfast provided, plenty of fluffy towels even down to non stick bath mats"
Australia
Stephanie
The price is ฿4,428
฿5,314 total
includes taxes & fees
8 Nov - 9 Nov
Peartree Serviced Apartments
A view from a window overlooking a street with a bus, a pedestrian crossing, and a sign indicating a speed limit of 30.

11. ANG Apartments

ANG Apartments
2.0 star property
Southsea
9.0 out of 10, Wonderful, (6 reviews)
"Nice place to stay, lovely beach view and close to amenities"
United Kingdom
Claire
The price is ฿2,732
฿2,732 total
includes taxes & fees
12 Oct - 13 Oct
ANG Apartments
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
"Staff were very efficient and helpful Hotel has lovely restaurant and bar Had a junior suite which was very clean And had everything you could require for the stay Hotel is situated in a great location Overall I would recommend this hotel to anyone visiting Southampton"
David 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:

  • View our selection of featured holiday rentals in Winchester
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  • 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.

How many holiday rentals are there in Winchester?

Expedia has 37 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 Theatre Royal Winchester. 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.