Winchester Trips (flight + hotel)

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Top hotels in Winchester

The Grosvenor

The Grosvenor

3 out of 5
26 Cains Terrace, Timaru
Fully refundableReserve now, pay when you stay
The price is P5,497 per night from Jul 22 to Jul 23
P5,497
P6,322 total
Jul 22 - Jul 23
includes taxes & fees
7.8/10 Good! (790 reviews)
"Character hotel with a fantastic old style elevator"

Reviewed on Jul 5, 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 P4,701 per night from Jul 20 to Jul 21
P4,701
P5,406 total
Jul 20 - Jul 21
includes taxes & fees
8.8/10 Excellent! (528 reviews)
"Very clean, comfy bed, lovely warm unit, 7min walk to the hospital. Perfect wee kitchenette that had everything i needed to prepare my meals. My only gripe would be the lack of secure window ventilation latches. I love to air out my room securely whilst im out. Easy fix tho. I will definitely be ..."

Reviewed on Jun 30, 2025

Aspen on King Motel
Bay Viaduct Motor Lodge

Bay Viaduct Motor Lodge

2.5 out of 5
10 Wai-Iti Rd, Maori Hill, Timaru
The price is P5,711 per night from Jul 31 to Aug 1
P5,711
P6,568 total
Jul 31 - Aug 1
includes taxes & fees
9.4/10 Exceptional! (121 reviews)
"Very well maintained and presented property, ours was a modern large spacious room. Good location. Nothing at all to fault which in itself is often rare these days. Would return without hesitation."

Reviewed on Jun 29, 2025

Bay Viaduct Motor Lodge
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 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.