Winchester Vacations from ￥170,894

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The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Glentanner Park Centre

Glentanner Park Centre

4.5 out of 5
per person
Aug 7 - Aug 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Timaru (TIU)
8.4/10 Very Good! (206 reviews)
Great camping option just outside MT Cook national park. We stayed in cabin with three bunk beds. Communal kitchen was fun to meet other campers especially students and families. Shower house was big and plenty of hot water. Much more affordable the hotels in the park.

Reviewed on May 31, 2025

Alpine Views Burkes Pass

Alpine Views Burkes Pass

3.5 out of 5
per person
Aug 7 - Aug 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Timaru (TIU)
9.8/10 Exceptional! (54 reviews)
Very nice place to stay, very beautiful mountain view, and very nice owner.

Reviewed on May 5, 2025

Burkes Pass Country Motel

Burkes Pass Country Motel

2.5 out of 5
per person
Aug 7 - Aug 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Timaru (TIU)
9.2/10 Wonderful! (193 reviews)
Loved this property. It was a short drive to Lake Tekapo for night sky viewing and cute pubs nearby for dinner. The property is great and the hosts are so lovely!

Reviewed on Apr 27, 2025

Gladstone Grand Hotel

Gladstone Grand Hotel

2 out of 5
per person
Aug 7 - Aug 11
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Timaru (TIU)
4.8/10 (9 reviews)
A beautiful old building in poor repair, could be really special. Dining area dingy and drab. Lack of information generally.

Reviewed on Apr 29, 2025

Find the Best Winchester Vacation Packages

Winchester Hotel Deals

Bay Viaduct Motor Lodge
Bay Viaduct Motor Lodge
2.5 out of 5
10 Wai-Iti Rd, Maori Hill, Timaru
Fully refundableReserve now, pay when you stay
The price is ￥13,328 per night from Jul 30 to Jul 31
￥13,328
￥15,327 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (119 reviews)
"Great little place to stay."

Reviewed on May 26, 2025

Bay Viaduct Motor Lodge
The Grosvenor
The Grosvenor
3 out of 5
26 Cains Terrace, Timaru
Fully refundableReserve now, pay when you stay
The price is ￥11,316 per night from Jul 3 to Jul 4
￥11,316
￥13,267 total
Jul 3 - Jul 4
includes taxes & fees
7.8/10 Good! (787 reviews)
One night stay, after a long day.
"Quaint room, and we were totally beat after driving all day. Was sad we missed out on the restaurant, but we settled in and hot shower + right to sleep. Nice bed, and good little fridge to keep our road snacks for the next day. My only qualm about this place is we paid for an Executive room, and ..."

Reviewed on Jun 12, 2025

The Grosvenor
Aspen on King Motel
Aspen on King Motel
4.5 out of 5
51 King Street, Timaru
Fully refundableReserve now, pay when you stay
The price is ￥11,999 per night from Jul 7 to Jul 8
￥11,999
￥14,021 total
Jul 7 - Jul 8
includes taxes & fees
8.8/10 Excellent! (527 reviews)
"Room very well equipped and renovated, bathroom cold, didnt use spa bath. Owner very friendly and helpful."

Reviewed on Jun 24, 2025

Aspen on King Motel
See all 75 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.

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from ￥170,894 on Expedia for your Winchester getaway. However, a range of 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?
May, June and July are the best times to look for cheap Winchester vacation packages. Opting to travel in less busy periods means you can typically find reduced prices on hotels and flights.
How many days is enough for Winchester?
With a well-planned itinerary, you can easily tick off the most popular Winchester sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Winchester vacation for longer.
How to find the best Winchester package deals?
Start your search for a Winchester package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Winchester package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winchester adventure off to a flying start.
Is it cheaper to book a Winchester vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Winchester vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Winchester?
If you have your Winchester travel dates confirmed, book as early as you can to score some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Winchester?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to go to Winchester.
  2. Budget wisely: As well as the cost of your accommodations, you'll need to factor in other expenses too. These include flights, food and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Winchester.
  3. Decide your trip length: Think about how long you want to spend exploring Winchester. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Winchester vacation package.

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