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.
Red Lion Hotel

Red Lion Hotel

3 out of 5
per person
Sep 3 - Sep 8
found 4 hours ago
Roundtrip flight included
Moncton (YQM) to Southampton (SOU)
8.2/10 Very Good! (1,005 reviews)
On site parking and easy access into town.

Reviewed on Jul. 27, 2025

Ettrick Court House By REDWOOD STAYS

Ettrick Court House By REDWOOD STAYS

3 out of 5
Rushmoor District
per person
Sep 8 - Sep 13
found 16 hours ago
Roundtrip flight included
Ottawa (YOW) to Southampton (SOU)
No reviews
Boutique Apartments by Viridian Apartments

Boutique Apartments by Viridian Apartments

4 out of 5
Rushmoor District
per person
Sep 8 - Sep 13
found 16 hours ago
Roundtrip flight included
Ottawa (YOW) to Southampton (SOU)
8.2/10 Very Good! (16 reviews)
Excellent but internet was a bit iffy

Reviewed on Apr. 15, 2025

Apollo Hotel

Apollo Hotel

4 out of 5
per person
Sep 3 - Sep 8
found 4 hours ago
Roundtrip flight included
Moncton (YQM) to Southampton (SOU)
7.2/10 Good! (1,001 reviews)
Great staff. Food was good and reasonably priced. Rooms were dated shower etc was like walking back into 1990. Towels werent changed or bedding cahnged stayed for 3 days. Ok for the price

Reviewed on Jun. 9, 2025

HQ Aparthotel Farnborough

HQ Aparthotel Farnborough

4 out of 5
Rushmoor District
per person
Sep 8 - Sep 13
found 16 hours ago
Roundtrip flight included
Ottawa (YOW) to Southampton (SOU)
9/10 Wonderful! (428 reviews)
Excellent experience

Reviewed on Jul. 27, 2025

Ready to book your vacation to Winchester?

 

Choose your dates

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 $162 per night from Aug 3 to Aug 4
CA $162
CA $195 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"Good location and close to the railway station"

Reviewed on Jul. 26, 2025

The Winchester Hotel & Spa
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 $126 per night from Aug 3 to Aug 4
CA $126
CA $151 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (864 reviews)
"Great..."

Reviewed on Jul. 21, 2025

voco Winchester Hotel & Spa by IHG
Norton Park Hotel, Spa & Manor House

Norton Park Hotel, Spa & Manor House

4 out of 5
Sutton Scotney, Winchester, England
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Aug 31 to Sep 1
CA $144
CA $173 total
Aug 31 - Sep 1
includes taxes & fees
7.8/10 Good! (998 reviews)
"Lovely place"

Reviewed on Jul. 30, 2025

Norton Park Hotel, Spa & Manor House
See all 3,157 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Winchester

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

Winchester Cathedral

5/5(17 reviews)

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

Courtesy of English Heritage

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

CA $362
per adult
88% of travellers recommend
Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor
Private Walking Tour of Southampton

Private Walking Tour of Southampton

CA $41
per adult
100% of travellers recommend
Private Walking Tour of Southampton
Southampton: Guided Ghost Walk

The Southampton Ghost Walk

CA $28
per adult
100% of travellers recommend
The Southampton Ghost Walk
See all activities in Winchester

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from CA $1,170 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.