Winchester Vacations from $906

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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.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Winchester Wessex Hotel by Sunday

Winchester Wessex Hotel by Sunday

4 out of 5
Price was $995, price is now $906 per person
$906
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Southampton (SOU)
7.4/10 Good! (1,006 reviews)
Plus is location. Unfortunately they chose to do a construction project directly below our room in the evening while we were trying to sleep and the nose was bad. Our room refrigerator did not work and overall the room and general condition of hotel is a bit worn and tired.

Reviewed on Oct 8, 2025

Derby Manor

Derby Manor

4 out of 5
Price was $1,378, price is now $1,127 per person
$1,127
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Southampton (SOU)
9.2/10 Wonderful! (613 reviews)
A lovely peaceful hotel, beautifully decorated. Pleasant staff. Relaxing bar and lounge. Good choice at breakfast. Free parking and ideally located with a shortish walk to the beach (via Toft zigzag). Not too far from town centre which is 5 mins by car.

Reviewed on Sep 22, 2025

Best Western Plus The Connaught Hotel & Spa

Best Western Plus The Connaught Hotel & Spa

4 out of 5
Bournemouth City Centre
Price was $1,271, price is now $1,104 per person
$1,104
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Southampton (SOU)
8.4/10 Very Good! (896 reviews)
Water pressure in Jacuzzi was extremely low so it was more of a warm bath. Room was very cold as heating has not been turned on mid September, however we were offered a portable heater and the heating was turned on. Room was disappointingly small. Great Choices for breakfast and staff were very accommodating and friendly. Eat in the restaurant on Thursday evening the special was excellent we were very impressed with the service our waiter customer service was extremely good 10/10

Reviewed on Oct 2, 2025

No.4 Carlton Hotel

No.4 Carlton Hotel

4 out of 5
The Polygon
Price was $1,195, price is now $1,045 per person
$1,045
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Southampton (SOU)
9.6/10 Exceptional! (113 reviews)
I could not find any fault with our stay. As it's a boutique hotel, there isn't any facility and restaurant; that could be the only minus.

Reviewed on Oct 10, 2025

room2 Southampton Hometel

room2 Southampton Hometel

4 out of 5
Southampton City Centre
Price was $993, price is now $908 per person
$908
per person
Nov 18 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Southampton (SOU)
9.4/10 Exceptional! (1,101 reviews)
Great stay! Room was quiet, clean and well stocked. Loved the restaurant downstairs!

Reviewed on Sep 30, 2025

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Discover the most popular places to visit in Winchester

Winchester Cathedral which includes a garden, a church or cathedral and religious elements

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
Marwell Wildlife which includes zoo animals and dangerous animals

Marwell Zoo

Head out on a safari in search of hippos, snow leopards and giraffes or check out unusual reptiles at this spacious zoo and wildlife park.

Marwell Zoo
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

What to do in Winchester

Courtesy of English Heritage

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

$272
per adult
88% of travellers recommend
Southampton: Post-Cruise Tour to London via Salisbury, Stonehenge and Windsor
Stonehenge Tour from Southampton to London

Stonehenge Tour from Southampton to London

$179
per adult
100% of travellers recommend
Stonehenge Tour from Southampton to London
Bombay Sapphire Distillery Tour and Tasting

Bombay Sapphire Gin Distillery Tour and Cocktail

$30
per adult
Bombay Sapphire Gin Distillery Tour and Cocktail
See all activities in Winchester

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
$101 nightly
The price is $121 total per night from Oct 19 to Oct 20
$121 total
Oct 19 - Oct 20
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
"Didn't use the spa"

Reviewed on Oct 4, 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
$84 nightly
The price is $101 total per night from Nov 9 to Nov 10
$101 total
Nov 9 - Nov 10
Total with taxes and fees
7.4/10 Good! (1,002 reviews)
"The service by the staff was impecible, the view was incredible out of our window and it's totally central so you can pop in and out and feel part of the city. It has an old fashioned charm whilst being neat, friendly and efficient. Well worth it."

Reviewed on Oct 6, 2025

Winchester Wessex Hotel by Sunday
Marwell Hotel Winchester South

Marwell Hotel Winchester South

3 out of 5
Thompson Lane, Winchester, England
Fully refundableReserve now, pay when you stay
$44 nightly
The price is $53 total per night from Oct 19 to Oct 20
$53 total
Oct 19 - Oct 20
Total with taxes and fees
7.6/10 Good! (1,002 reviews)
"The parking was good, the bar was good, my disappointment was I wanted 1slice of toast and a cup of coffee, I take meds in the morning and can only eat minimally, they said I had to pay £10.80 p that was the cheapest on the breakfast menu, I declined and went elsewhere,"

Reviewed on Oct 2, 2025

Marwell Hotel Winchester South
See all 3,268 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.

Winchester Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southampton Airport (SOU)
Population
40,000
Max Temp Winter
45ºF
Max Temp Summer
70ºF
Top Sights
Winchester Cathedral, Marwell Zoo and Winchester Science Centre and Planetarium

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $906 on Expedia for your Winchester escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
You can typically find lower rates and better availability in May, June and December. Take a look at our cheap Winchester vacation packages and you could get some great off-season deals.
How many days is enough for Winchester?
With around 2 days, you'll have plenty of time to experience popular neighborhoods like Sparsholt and Littleton during your Winchester vacation. Be sure to also add Winchester Science Centre and Planetarium and Great Hall to your sightseeing itinerary. Searching for more adventures? Consider venturing outside of Winchester on tours and day trips.
Is it worth booking a vacation package to Winchester?
Popular for its walking trails, nightlife and culture, a Winchester vacation is a hit with all kinds of visitors. Be sure to check out main sights like Winchester Cathedral and Great Hall, and consider renting a set of wheels for day trips to discover even more.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Winchester package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester escape off to a flying start.
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 flights and stays individually. Better still, you can tailor your Winchester getaway to match your exact needs. 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?
Enjoy incredible bargains by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Winchester getaway.
How to plan a trip to Winchester?

  1. Choose when to get away: Check your schedule and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to escape to Winchester.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your hotel will likely be the largest expense during your trip to Winchester.
  3. Organize your Winchester escape with our trip planning tool: Search for and book accommodations and activities all in one place. You can also collaborate with your group to plan an unforgettable trip to Winchester together.
  4. Determine how many days away: Start by making a list of all the attractions you want to get to in Winchester. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Winchester vacation package for you.
  6. Book any excursions or activities: Here's the fun part — locking in everything you want to see and do. Browse some of the top things to do in Winchester and book your tickets in advance to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Your Winchester getaway is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've teamed up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.

Explore a world of travel with Expedia

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