Winchester Vacations

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Winchester Hotel Deals

Anchor Motel

Anchor Motel

2.5 out of 5
42 Evans St Timaru
Fully refundableReserve now, pay when you stay
$46 nightly
The price is $53 total per night from Jun 30 to Jul 1
$53 total
Jun 30 - Jul 1
Total with taxes and fees
8/10 Very Good! (220 reviews)
"Whole house. Very old house which was actually quite an experience..pull chord for lights and shower over claw foot bath, took me back to my 20's.. 1 full length mirror somewhere, would be great!! But iron and board were very helpful! Needs some work on both bathrooms! Extractor fan in kitchen VERY ..."

Reviewed on Jun 3, 2026

Anchor Motel
The Grosvenor

The Grosvenor

3 out of 5
26 Cains Terrace Timaru
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $95 total per night from Jun 27 to Jun 28
$95 total
Jun 27 - Jun 28
Total with taxes and fees
8/10 Very Good! (846 reviews)
"Loved my stay. Great hotel with lovely rooms."

Reviewed on Jun 4, 2026

The Grosvenor
Aaron Court Motel

Aaron Court Motel

2 out of 5
27 Evans St Timaru Canterbury
Fully refundableReserve now, pay when you stay
$46 nightly
The price is $53 total per night from Jun 24 to Jun 25
$53 total
Jun 24 - Jun 25
Total with taxes and fees
6.8/10 (138 reviews)
"Photos uploaded"

Reviewed on Jun 14, 2026

Aaron Court Motel
See all 80 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.

Find the Best Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
New Zealand dollars
Closest Airport
Richard Pearse Airport (TIU)
Top Sights
DB Brewery, Geraldine Vintage Car and Machinery Museum and Geraldine Observatory

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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?
February, November and December are the best times to look for cheap Winchester vacation packages. Traveling in quieter periods means you can typically find lower prices on flights and accommodations.
How many days is enough for Winchester?
The ideal length for your Winchester vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to tick off all the main attractions and discover some hidden gems along the way.
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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're like us, you love traveling the world but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Winchester trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.