City of Winchester Holidays

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Top destinations in City of Winchester

A large stone castle with multiple towers and battlements.
FlightsFlightsHotelsHotels

Southampton

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

Winchester

Top hotels in City of Winchester

Meon Valley Hotel, Spa & Golf

Meon Valley Hotel, Spa & Golf

4 out of 5
Sandy Lane Southampton England
Fully refundableReserve now, pay when you stay
The price is S$112 per night from 9 Aug to 10 Aug
S$112
9 Aug - 10 Aug
includes taxes & fees
7/10 Good! (1,011 reviews)
"Had a great stay , room clean, staff very accommodating and friendly Some parts need a bit of painting and updating. Shame we couldn’t have any treatments didn’t realise that they didn’t do any on a Sunday Food was lovely."

Reviewed on 13 Jul, 2026

Meon Valley Hotel, Spa & Golf
The Winchester Hotel & Spa

The Winchester Hotel & Spa

4 out of 5
Worthy Lane Winchester England
Fully refundableReserve now, pay when you stay
The price is S$178 per night from 2 Aug to 3 Aug
S$178
2 Aug - 3 Aug
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"Rooms was absolutely spotless and very clean. Staff were also absolutely amazing. However I did find the spa facilities a little dated and also ali"

Reviewed on 13 Jul, 2026

The Winchester Hotel & Spa
New Place

New Place

4 out of 5
Shirrell Heath Southampton England
Fully refundableReserve now, pay when you stay
The price is S$112 per night from 19 Jul to 20 Jul
S$112
19 Jul - 20 Jul
includes taxes & fees
8.4/10 Very good! (1,010 reviews)
"The main building and gardens are beautiful and well maintained. Unfortunately our room was on the small side. The safe was broken and our window was difficult to open. A member of staff kindly came to our room to help us. The window had stuck and it needed a forceful shove to open. Also while we ..."

Reviewed on 13 Jul, 2026

New Place
See all 6,291 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.

Stay near popular City of Winchester attractions

A historic cathedral with tall spires and large stained glass windows.

Winchester Cathedral

9.4/10 (713 reviews)
With its exquisite artwork and fascinating historical relics, Winchester’s Gothic masterpiece is thought to be one of the nation’s finest cathedrals.
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What to do in City of Winchester

From Portsmouth: Isle of Wight Day Tour by Bus and Ferry

From Portsmouth: Isle of Wight Day Tour by Bus and Ferry

S$136
per adult
From Portsmouth: Isle of Wight Day Tour by Bus and Ferry
Stonehenge Tour from Southampton to London

Stonehenge Tour from Southampton to London

S$236
per adult
98% of travellers recommend
Stonehenge Tour from Southampton to London
Portsmouth: Portsmouth of the Past Walking Tour

Portsmouth: Portsmouth of the Past Walking Tour

S$17
per adult
Portsmouth: Portsmouth of the Past Walking Tour
See all activities in City of Winchester

* 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.