A cathedral at night with illuminated trees and a park with benches.

Holiday Rentals in City of Winchester

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Top Cities in City of Winchester

Our top choices for City of Winchester holiday rentals

1. Settle Winchester

Settle Winchester
2.0 star property
Winchester City Center
The price is €109
includes taxes & fees
9 Nov - 10 Nov
Settle Winchester

2. The Shack Cabin Sleeps 3 With Enclosed Garden

The Shack Cabin Sleeps 3 With Enclosed Garden
2.0 star property
Waterlooville
The price is €172
includes taxes & fees
19 Nov - 20 Nov
The Shack Cabin Sleeps 3 With Enclosed Garden

3. The Riley Stable- Cozy Getaway

The Riley Stable- Cozy Getaway
2.5 star property
Waterlooville
The price is €158
includes taxes & fees
9 Nov - 10 Nov
The Riley Stable- Cozy Getaway

4. Barley Cottage

Barley Cottage
3.0 star property
Alresford
The price is €925
includes taxes & fees
11 Nov - 12 Nov
Barley Cottage

5. Suetts Farm Barns

Suetts Farm Barns
3.0 star property
Southampton
The price is €1,130
includes taxes & fees
11 Nov - 12 Nov
Suetts Farm Barns

6. Second Nature Southampton

Second Nature Southampton
4.0 star property
Southampton City Centre
9.4 out of 10, Exceptional, (1,366 reviews)
"Great location and friendly staff!"
United States
Gary
The price is €92
includes taxes & fees
13 Nov - 14 Nov
Second Nature Southampton

7. Southampton Serviced Apartment

Southampton Serviced Apartment
4.0 star property
Bassett
8.6 out of 10, Excellent, (188 reviews)
"Clean rooms, spacious enough for two for a weekend/long weekend. Easy access to Southampton City centre on the No1 bus, which runs right past the front door. Plenty of parking front and rear to service all the apartments."
United Kingdom
Emma
The price is €216
includes taxes & fees
12 Nov - 13 Nov
Southampton Serviced Apartment

8. 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
Stunning 2-bed Apt, Sleeps 6 in The New Forest

9. Settle Southampton

Settle Southampton
2.0 star property
Freemantle
8.2 out of 10, Very good, (14 reviews)
"Brilliant property really well situated for the centre of town. Deffo coming back."
United Kingdom
Chris
The price is €120
includes taxes & fees
15 Nov - 16 Nov
Settle Southampton

10. Peartree Serviced Apartments

Peartree Serviced Apartments
3.5 star property
Salisbury
9.6 out of 10, Exceptional, (329 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 €125
includes taxes & fees
22 Nov - 23 Nov
Peartree Serviced Apartments

11. Beddoe Apartments

Beddoe Apartments
3.0 star property
Eastleigh
7.8 out of 10, Good, (20 reviews)
"Ideal for couple of nights stay. Easy parking was a bonus. "
United Kingdom
Alan
The price is €234
includes taxes & fees
15 Nov - 16 Nov
Beddoe Apartments

12. Stone Circle Glamping

Stone Circle Glamping
2.0 star property
Durrington
8.6 out of 10, Excellent, (21 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 €65
includes taxes & fees
9 Nov - 10 Nov
Stone Circle Glamping

13. Pinnacle Suites

Pinnacle Suites
3.0 star property
Cowes
9.2 out of 10, Wonderful, (42 reviews)
"A great stay in this unique, cool venue."
United Kingdom
Simon
The price is €154
includes taxes & fees
22 Nov - 23 Nov
Pinnacle Suites

14. Cleveland Road

Cleveland Road
2.0 star property
Southsea
The price is €107
includes taxes & fees
9 Nov - 10 Nov
Cleveland Road

15. HQ Aparthotel Farnborough

HQ Aparthotel Farnborough
4.0 star property
Rushmoor District
9.2 out of 10, Wonderful, (483 reviews)
"I always stay here when visiting family nearby as I live in USA."
United States
John
The price is €82
includes taxes & fees
15 Nov - 16 Nov
HQ Aparthotel Farnborough

16. Orchard Road

Orchard Road
2.0 star property
Southsea
The price is €54
includes taxes & fees
9 Nov - 10 Nov
Orchard Road

17. 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 €146
includes taxes & fees
23 Nov - 24 Nov
Charles Hope Salisbury Centre

18. Caravan - Sleeps 6 With Parking and Terrace

Caravan - Sleeps 6 With Parking and Terrace
3.0 star property
Hayling Island
The price is €202
includes taxes & fees
10 Nov - 11 Nov
Caravan - Sleeps 6 With Parking and Terrace

19. Francis Avenue

Francis Avenue
2.0 star property
Southsea
The price is €65
includes taxes & fees
9 Nov - 10 Nov
Francis Avenue

20. Hamilton House

Hamilton House
Southsea
The price is €122
includes taxes & fees
14 Nov - 15 Nov
Hamilton 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 City of Winchester Hotel Reviews

Find out more about City of Winchester

Everything you need to know about City of Winchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the City of Winchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect City of Winchester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

City of Winchester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in City of Winchester. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A City of Winchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of City of Winchester holiday rentals we have selected for you start as low as €65 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on City of Winchester rentals

At Expedia, we put the best City of Winchester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top City of Winchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream City of Winchester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around City of Winchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.