City of Winchester Holidays

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in City of Winchester

Southampton showing heritage elements, a castle and heritage architecture
FlightsFlightsHotelsHotels

Southampton

Southampton

Top Flight + Hotel Deals in City of Winchester

Price found within the past 48 hours. Click for updated prices.
Leonardo Hotel Southampton

Leonardo Hotel Southampton

4 out of 5
The Polygon
Price was €231, price is now €190 per person
€190
per person
11 Dec - 13 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
8.4/10 Very Good! (1,200 reviews)
Good location, friendly staff, good buffet breakfast

Reviewed on 6 Nov 2025

No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
The Polygon
Price was €431, price is now €345 per person
€345
per person
11 Dec - 13 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
9.6/10 Exceptional! (122 reviews)
Decor, hotel quality, and cleanliness was excellent. Lots of great amenities included. Guest service was friendly and efficient. Important to note that there is no elevator. Also, glassed in bathroom was not very private and sound through ceiling and room door was very noticeable.

Reviewed on 23 Oct 2025

Bartley Lodge Hotel

Bartley Lodge Hotel

4 out of 5
Price was €252, price is now €214 per person
€214
per person
11 Dec - 13 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
7.6/10 Good! (264 reviews)
Better lighting in car park when it's dark. Difficult to see where the disabled spaces are

Reviewed on 15 Sept 2025

Novotel Southampton

Novotel Southampton

4 out of 5
Southampton City Centre
Price was €227, price is now €199 per person
€199
per person
11 Dec - 13 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
8/10 Very Good! (1,014 reviews)
Too hot! And we visited in November so couldn’t imagine how unbearable it would be in the summer. And bath if your bigger than a size 14 you won’t fit and no way a man would fit and showers no power so may as well of had a kid stand over me with a watering can. Rooms need updating.

Reviewed on 7 Nov 2025

Best Western Chilworth Manor Hotel

Best Western Chilworth Manor Hotel

3 out of 5
Price was €241, price is now €212 per person
€212
per person
11 Dec - 13 Dec
found 1 day ago
Return flight included
Dublin (DUB) to Southampton (SOU)
8/10 Very Good! (1,008 reviews)
Just as expected with a quality facility and good value

Reviewed on 3 Oct 2025

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! (1,005 reviews)
Very good hotel. All very clean. Didn’t get my drinks vouchers which was disappointing.

Reviewed on 1 Nov 2025

Get rates
The Winchester Hotel & Spa
Meon Valley Hotel, Golf & Country Club

Meon Valley Hotel, Golf & Country Club

4 out of 5
Sandy Lane, Shedfield, Southampton, England
Fully refundableReserve now, pay when you stay
The price is €56 per night from 16 Nov to 17 Nov
€56
16 Nov - 17 Nov
includes taxes & fees
6.8/10 (1,001 reviews)
Gym good , breakfast limited

Reviewed on 6 Nov 2025

Meon Valley Hotel, Golf & Country Club
New Place

New Place

4 out of 5
Shirrell Heath, Southampton, England
Fully refundableReserve now, pay when you stay
The price is €65 per night from 7 Dec to 8 Dec
€65
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Relax and enjoy the ambiance!

Reviewed on 29 Oct 2025

New Place
See all 5,654 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 €190. 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.