City of Winchester Vacations & Trips from ￥277,983

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Top destinations in City of Winchester

A large stone castle with multiple towers and battlements.
FlightsFlightsHotelsHotels

Southampton

Southampton

The Latest City of Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Premier Inn Farnborough West - Southwood

Premier Inn Farnborough West - Southwood

3 out of 5
Rushmoor District
Price was ￥278,734, price is now ￥277,983 per person
￥277,983
per person
Sep 19 - Sep 22
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Southampton (SOU)
5.6/10 (4 reviews)
I checked in late, to welcoming and patient staff. Parking was a breeze, as was finding my room, and resting my head and falling right asleep because it was so peaceful and quiet. It was just what I needed to decompress.

Reviewed on Oct 22, 2025

Apple Tree Place B&B

Apple Tree Place B&B

4 out of 5
Price was ￥279,756, price is now ￥278,735 per person
￥278,735
per person
Sep 20 - Sep 22
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Southampton (SOU)
9.6/10 Exceptional! (46 reviews)
Good size room with everything you need, really good breakfast

Reviewed on Jul 7, 2026

City of Winchester Hotel Deals

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 ￥18,614 per night from Aug 2 to Aug 3
￥18,614
￥22,337 total
Aug 2 - Aug 3
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
"The staff were very helpful and hotel was very clean but the air con didn't really work. Only the left hand corner produced any air. Room was hot even with the fan provided. Not good enough for the price paid. The cold water always ran hot for a couple of minutes. Which I thought was strange but ..."

Reviewed on Jul 8, 2026

The Winchester Hotel & Spa
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 ￥11,795 per night from Jul 12 to Jul 13
￥11,795
￥14,154 total
Jul 12 - Jul 13
includes taxes & fees
7/10 Good! (1,005 reviews)
"Golfing facilities and bar superb. Buildings looking dated and tired"

Reviewed on Jul 9, 2026

Meon Valley Hotel, Spa & Golf
New Place

New Place

4 out of 5
Shirrell Heath Southampton England
Fully refundableReserve now, pay when you stay
The price is ￥11,431 per night from Aug 5 to Aug 6
￥11,431
￥13,718 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"I really love the customer service and the environment Really had a good time, excellent food"

Reviewed on Jul 9, 2026

New Place
See all 6,139 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 vacation package cost?
Custom build your City of Winchester package from just ￥277,983. 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 vacation 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 vacation?
Travelers 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. Vacationing 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 vacation 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 vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your accommodations 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 vacation 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 vacation package?
We totally get it — sometimes life doesn't go according to plan. If you've booked a City of Winchester vacation 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

Iconic Spinnaker Tower, Portsmouth

Spinnaker Tower Portsmouth All Day Admission Ticket

￥4,199
per adult
Spinnaker Tower Portsmouth All Day Admission Ticket
Stonehenge Tour from Southampton to London

Stonehenge Tour from Southampton to London

￥29,125
per adult
98% of travellers recommend
Stonehenge Tour from Southampton to London
Isle of Wight: Osborne Admission Ticket

Isle of Wight: Osborne Admission Ticket

￥5,125
per adult
100% of travellers recommend
Isle of Wight: Osborne Admission Ticket
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.