City of Winchester Holidays

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    Save up to €185 when you book a flight and hotel together*

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Top destinations in City of Winchester

Southampton showing heritage elements, a castle and heritage architecture
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Southampton

Southampton

Top Flight + Hotel Deals in City of Winchester

Price found within the past 48 hours. Click for updated prices.
The Elephant at the Market

The Elephant at the Market

3.5 out of 5
Save 100% on your flight
Price was €443, price is now €358 per person
€358
per person
22 Apr - 30 Apr
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
8.2/10 Very Good! (176 reviews)
Nice staff. Great central location with parking. The room was lovely and very comfortable.

Reviewed on 7 Jan 2026

Top hotels in City of Winchester

The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
Fully refundableReserve now, pay when you stay
8.4/10 Very Good! (1,001 reviews)
Room was clean and staff very helpful.

Reviewed on 7 Feb 2026

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The Winchester Hotel & Spa
Norton Park Hotel, Spa & Manor House

Norton Park Hotel, Spa & Manor House

4 out of 5
Sutton Scotney Winchester England
Fully refundableReserve now, pay when you stay
The price is €99 per night from 15 Feb to 16 Feb
€99
15 Feb - 16 Feb
includes taxes & fees
7.8/10 Good! (1,001 reviews)
The room was very clean, and the facilities were fantastic

Reviewed on 3 Feb 2026

Norton Park Hotel, Spa & Manor House
Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Paternoster Row Winchester England
Fully refundableReserve now, pay when you stay
The price is €75 per night from 12 Feb to 13 Feb
€75
12 Feb - 13 Feb
includes taxes & fees
7.4/10 Good! (1,003 reviews)
Both receptionist and dua in the bar were beyond helpful and lovely. It was great that they made such a fuss of my dogs. The rooms are very clean but definitely need an update of furniture and decoration. But I would still choose to stay at this friendly hotel

Reviewed on 29 Jan 2026

Winchester Wessex Hotel by Sunday
See all 5,480 properties in City of Winchester
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.

Frequently asked questions

How much does a City of Winchester holiday package cost?
Custom build your City of Winchester package from just €358. Choose from any combination of flights, hotels and rental cars to craft the escape you've been dreaming of. Remember to add on a few experiences or activities!
How do I get a cheap travel package to City of Winchester?
Our City of Winchester holiday packages offer plenty of savings for the savvy explorer. For the best deal, simply combine your flights, hotels and extras (including activities) into a handy package. But cheap prices are just the beginning of your next memorable adventure. When you book with Expedia, and you'll have over 550 airlines and 1,000,000 hotels around the globe to pick from. Whatever your budget or style, there's a package here just for you.
Where should I stay in City of Winchester?
If you're eager to see popular sights such as Winchester Cathedral and Great Hall, head straight for Winchester. You might want to stay a while to fully experience this buzzing city.
What are the top hotels in City of Winchester?
When it comes to properties in Winchester, Winchester Royal Hotel and Mercure Wessex Winchester Hotel are two fantastic options. If you're visiting Fareham, Moxy Southampton and Leonardo Hotel Southampton - Formerly Jurys Inn will make you feel at home.
How far in advance should I book my City of Winchester holiday?
Travellers can normally compare international fares on Expedia within 12 months of departure. Booking late? With a little bit of luck, it's still possible to score an affordable ticket just weeks before your flight.
What does an Expedia City of Winchester travel package include?
From airfares and hotels to car rentals, Expedia can help you craft a City of Winchester package that suits you. Holidaying for a week or two? Look into a flight, rental car and hotel bundle. If you can only manage a quick getaway, a flight and hotel deal may be more your style. Activities can also be added once you've made your booking. Our holiday packages make it easy to save and plan.
What should I know before booking a City of Winchester travel package?
Whether it's adventure or relaxation you're seeking, a City of Winchester holiday package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a City of Winchester Expedia holiday package?
Expedia offers access to more than 550 airline partners globally, so you definitely can. Just pick the carrier that suits you and craft your ideal City of Winchester escape.
If I'm not able to travel, can I cancel my City of Winchester holiday package?
We totally get it — sometimes life doesn't go according to plan. If you've booked a City of Winchester holiday package and have to cancel or change it, we can help. We recommend browsing our Customer Service Portal first for information. But in general, if you've taken out your package in the last 24 hours, you may be able to change your itinerary for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a fee.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.