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

Winchester Holiday Rentals

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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 S$151
includes taxes & fees
8 Nov - 9 Nov
Settle Winchester
A bedroom with a bed, a nightstand, a lamp, a window with a view, and a radiator.

2. Clifton Lodge

Clifton Lodge
2.0 star property
Winchester
The price is S$980
includes taxes & fees
16 Oct - 17 Oct
Clifton Lodge
A modern interior with a red sofa, black chairs, and a patterned floor.

3. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,353 reviews)
"Great location and friendly staff!"
United States
Gary
The price is S$134
includes taxes & fees
8 Nov - 9 Nov
Second Nature Southampton
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 S$176
includes taxes & fees
11 Oct - 12 Oct
Settle Southampton
A corner room with a large window overlooking a city street and buildings.

5. 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 S$216
includes taxes & fees
1 Nov - 2 Nov
Ocean Quay Luxury - Stylish 2 Bed - Has Parking
A building with a gravel driveway, a door, and two potted trees.

6. Barley Cottage

Barley Cottage
3.0 star property
Alresford
The price is S$1,189
includes taxes & fees
5 Nov - 6 Nov
Barley Cottage
A bedroom with a bed, a wooden bench, a staircase, and a wall-mounted light fixture.

7. Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.2 out of 10, Wonderful, (41 reviews)
"Very friendly host with modern suites"
United Kingdom
Samuel
The price is S$215
includes taxes & fees
11 Oct - 12 Oct
Pinnacle Suites
A bedroom with a large bed, a sofa, a TV, and a window with blinds.

8. QE2 Loft Apartments

QE2 Loft Apartments
3.0 star property
Southampton City Centre
5.6 out of 10, (15 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 S$258
includes taxes & fees
10 Oct - 11 Oct
QE2 Loft Apartments
A bedroom with a bed, a TV, and a window with curtains.

9. 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 S$474
includes taxes & fees
9 Oct - 10 Oct
Bayview Apartments
A view from a window overlooking a street with a bus, a pedestrian crossing, and a sign indicating a speed limit of 30.

10. 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 S$104
includes taxes & fees
9 Oct - 10 Oct
ANG Apartments
A bedroom with two beds, a nightstand with a lamp, and wall art.

11. 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
7.8 out of 10, Good, (6 reviews)
"The room was exactly as described. Communications with staff were clear and prompt. Check-in/Check-out was easy. Double bed was a nice firm mattress. Building was super quiet overnight. Location was very easy to access."
United Kingdom
Audrey
The price is S$110
includes taxes & fees
9 Oct - 10 Oct
Ground-Floor Family Studio Apartment with Double and Single Beds – Free Parking
A sign for Hotel Peartree, a serviced apartment, with contact information and website.

12. 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 S$186
includes taxes & fees
8 Nov - 9 Nov
Peartree Serviced Apartments
A living room with a dark blue sofa, a round wooden coffee table, a dining table with chairs, a large abstract painting, a round mirror, and a window with curtains.

13. Charles Hope Salisbury Centre

Charles Hope Salisbury Centre
4.0 star property
Salisbury
9.4 out of 10, Exceptional, (10 reviews)
"Clean modern room, well equipped and great locaton"
United Kingdom
Theodros
The price is S$192
includes taxes & fees
11 Oct - 12 Oct
Charles Hope Salisbury Centre
A building with multiple windows and doors, illuminated by green and white lights.

14. Ground-Floor Super King or Twin Studio Apartment with Free Private Parking

Ground-Floor Super King or Twin Studio Apartment with Free Private Parking
2.0 star property
Southsea
The price is S$108
includes taxes & fees
16 Oct - 17 Oct
Ground-Floor Super King or Twin Studio Apartment with Free Private Parking
A kitchen with grey cabinets, a microwave, an oven, a sink, and a wooden countertop.

15. Stunning 2-bed Apt, Sleeps 6 in The New Forest

Stunning 2-bed Apt, Sleeps 6 in The New Forest
4.0 star property
Southampton
The price is S$384
includes taxes & fees
11 Oct - 12 Oct
Stunning 2-bed Apt, Sleeps 6 in The New Forest
A narrow stream with clear water, surrounded by lush greenery and wildflowers.

16. Roslyn

Roslyn
2.0 star property
Romsey
The price is S$875
includes taxes & fees
19 Oct - 20 Oct
Roslyn
A building with multiple windows and doors, illuminated by green and white lights.

17. Ground-Floor Queen Bed Studio Apartment with Free Parking

Ground-Floor Queen Bed Studio Apartment with Free Parking
2.0 star property
Southsea
The price is S$103
includes taxes & fees
11 Oct - 12 Oct
Ground-Floor Queen Bed Studio Apartment with Free Parking
A tent with a bed inside, a colorful rug, and a sign on the ground.

18. 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 S$74
includes taxes & fees
9 Oct - 10 Oct
Stone Circle Glamping
A beach with a clear sky, calm sea, and a distant ship.

19. Loft 2bed Appartment with EVCharger

Loft 2bed Appartment with EVCharger
2.0 star property
Southsea
The price is S$162
includes taxes & fees
11 Oct - 12 Oct
Loft 2bed Appartment with EVCharger
A hotel room with a bed, a desk, a chair, a television, and a window.

20. Studio 32-Free Private Parking

Studio 32-Free Private Parking
2.0 star property
Southsea
The price is S$107
includes taxes & fees
20 Oct - 21 Oct
Studio 32-Free Private 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.
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Top Winchester Hotel Reviews

Moxy Southampton

Moxy Southampton

8/10 Good
"Not enough staff. The breakfast was cold and not enough. No one cleaned the tables or were too slow. Not accommodating when arrived early to check in."
Roberta 2-night trip
Posted 3 hours ago
Moxy Southampton

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.