City of Winchester Holidays

    deals illustration

    Better together

    Save up to S$134 when you book a flight and hotel together*
    stays illustration

    Find the right fit

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

    Rest easy

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

Top destinations in City of Winchester

Southampton which includes heritage architecture, heritage elements and a castle
FlightsFlightsHotelsHotels

Southampton

Southampton
Winchester which includes a fountain and heritage architecture
FlightsFlightsHotelsHotels

Winchester

Winchester

Top hotels in City of Winchester

New Place
New Place
4 out of 5
Shirrell Heath, Southampton, England
Fully refundableReserve now, pay when you stay
The price is S$111 per night from 20 Jul to 21 Jul
S$111
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Nice place
"Very nice place, but we expected to sleep in the manor and we were in one of the chalets. It was fine. The bathroom had dead mosquitoes stuck to the wall but other than that it was clean. Breakfast lacked some love. Also ordering drinks at the bar at night wasn’t easy. Rather a long wait and not ..."

Reviewed on 5 Jul, 2025

New Place
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! (1,000 reviews)
"Was a wonderful experience. Comfortable rooms and friendly staff!"

Reviewed on 1 Jul, 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 S$96 per night from 13 Jul to 14 Jul
S$96
13 Jul - 14 Jul
includes taxes & fees
6.8/10 (1,002 reviews)
"Nice hotel, good golf course"

Reviewed on 5 Jul, 2025

Meon Valley Hotel, Golf & Country Club
See all 5,657 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 . 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.