Winchester Vacation Packages

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Your Winchester Vacation

The rich history and welcoming locals are just the start of the things Winchester has on offer. Discover the very best of this city the way you want with a customized Winchester vacation package. If your trip to Winchester includes a little sightseeing, visit popular attractions like Winchester Cathedral, Great Hall and Winchester Christmas Market. Whoever you're escaping with and whatever the size of your budget, your ultimate Winchester vacation is only clicks away with Expedia.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Warbrook House Heritage Hotel

Warbrook House Heritage Hotel

4 out of 5
Price was CA $1,312, price is now CA $1,199 per person
CA $1,199
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Southampton (SOU)
7.6/10 Good! (753 reviews)
Because of the age of the building there was no air conditioning. And only a tiny fan in the round. 10” I found it was just to unbearable to sleep. Warm day and room above the kitchen. One member of staff said to mention to reception. She said they have a lot of people say about it and they should be doing something about it. Was I was checking out and mentioned to the lady there. She brushed me off and I felt awkward and hurt. She did not care.

Reviewed on Aug. 19, 2025

Ready to book your vacation to Winchester?

 

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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 CA $153 per night from Aug 25 to Aug 26
CA $153
CA $184 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"Bus park in front."

Reviewed on Aug. 17, 2025

The Winchester Hotel & Spa
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 CA $116 per night from Aug 31 to Sep 1
CA $116
CA $139 total
Aug 31 - Sep 1
includes taxes & fees
7.4/10 Good! (1,012 reviews)
Our stay
"Didn't eat at hotel mainly good cleanliness however toilet bowl very stained needed bleach and a scrub. Bed comfy nice view basic group ideal for one night"

Reviewed on Aug. 17, 2025

Winchester Wessex Hotel by Sunday
voco Winchester Hotel & Spa by IHG

voco Winchester Hotel & Spa by IHG

4 out of 5
Telegraph Way Morn Hill, Winchester, England
Fully refundable
The price is CA $119 per night from Aug 25 to Aug 26
CA $119
CA $143 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (876 reviews)
"Very modern and clean but with small, uncomfortable bathroom. Staff were lovely"

Reviewed on Aug. 18, 2025

voco Winchester Hotel & Spa by IHG
See all 3,247 properties in 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.
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Discover the most popular places to visit in Winchester

Winchester Cathedral featuring a park, heritage architecture and a church or cathedral

Winchester Cathedral

With its exquisite artwork and fascinating historical relics, Winchester’s Gothic masterpiece is thought to be one of the nation’s finest cathedrals.

Winchester Cathedral
Winchester Science Centre and Planetarium

Winchester Science Centre and Planetarium

Try out an extensive selection of interactive exhibits and lose yourself in deep space at one of the U.K.’s largest digital planetariums.

Winchester Science Centre and Planetarium
Hospital of St Cross featuring heritage architecture

Hospital of St Cross

Set within tranquil gardens, England’s oldest charitable institution features traditional 15th-century architecture and a stunning Norman church.

Hospital of St Cross

What to do in Winchester

Journey Through Winchester's Past: Private Tour

Journey Through Winchester's Past: Private Tour

CA $167
per traveller
Journey Through Winchester's Past: Private Tour
Stonehenge Tour from Southampton to London

Stonehenge Tour from Southampton to London

CA $244
per adult
100% of travellers recommend
Stonehenge Tour from Southampton to London
Courtesy of English Heritage

Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor

CA $365
per adult
88% of travellers recommend
Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor
See all activities in Winchester

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from CA $1,199 on Expedia for your Winchester escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
January, February and November are the best times to look for cheap Winchester vacation packages. Travelling in quieter months means you'll typically find better prices on flights and accommodations.
How many days is enough for Winchester?
Winchester vacations come in all shapes and sizes, but to get a true feel for this destination, we'd suggest 2 days is a good ballpark. In this timeframe, you can fit in top sights like Winchester Science Centre and Planetarium and Winchester City Mill and track down some hidden gems. Don't miss out on neighbourhoods such as Littleton and Sparsholt either. If you plan wisely, you can even take a day trip or two from Winchester too.
Is it worth booking a vacation package to Winchester?
Whether you'd like to explore major attractions like Winchester Cathedral and Winchester Christmas Market on your Winchester vacation, or coming for its excellent views, nightlife and walking trails, there's something for everyone here. With so many things to do, you'll quickly learn why so many visitors think Winchester is a good vacation destination.
How to find the best Winchester package deals?
Bagging a cheap Winchester package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Winchester package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging stays and flights separately. Better still, you can personalize your Winchester trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winchester?
If you have your Winchester vacation dates finalized, book as soon as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your diary and get packing. Your preferred time of year and the available activities will also help you decide when to escape to Winchester.
  2. Calculate your budget: Make sure you have enough money to cover everything from transportation and food to activities and airfares. Your accommodations will probably be the largest expense during your trip to Winchester.
  3. Decide how long to go for: Now that you're up to speed on Winchester, you can work out the ideal length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a customized Winchester vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.