Winchester Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top hotels in Winchester

Anchor Motel

Anchor Motel

2.5 out of 5
42 Evans St Timaru
Fully refundableReserve now, pay when you stay
The price is €51 per night from 4 Jul to 5 Jul
€51
4 Jul - 5 Jul
includes taxes & fees
8/10 Very good! (222 reviews)
"Everything was excellent. But the room was really cold, even with the heater on full."

Reviewed on 2 Jul 2026

Anchor Motel
The Grosvenor

The Grosvenor

3 out of 5
26 Cains Terrace Timaru
Fully refundableReserve now, pay when you stay
The price is €88 per night from 3 Jul to 4 Jul
€88
3 Jul - 4 Jul
includes taxes & fees
8/10 Very good! (848 reviews)
"At check in the receptionist didn’t bother to acknowledge us, still sitting when we approached the desk and said hello. Be aware, they are still under renovation! Nobody told us that… The carpet in the hallway and room from the 80’s, everything else painted white. Royal visit… no way."

Reviewed on 1 Jul 2026

The Grosvenor
Parklands Motor Lodge Timaru

Parklands Motor Lodge Timaru

3.5 out of 5
65-67 Evans Street Timaru
The price is €77 per night from 5 Jul to 6 Jul
€77
5 Jul - 6 Jul
includes taxes & fees
Parklands Motor Lodge Timaru
See all 79 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.

What to do in Winchester

Mount Cook Day tour from Christchurch to Queenstown

Mount Cook Day tour from Christchurch to Queenstown

€193
per adult
Mount Cook Day tour from Christchurch to Queenstown
Mt. Cook Full Day Group Tour via Tekapo from Christchurch

Mt. Cook Full Day Group Tour via Tekapo from Christchurch

€161
per adult
Mt. Cook Full Day Group Tour via Tekapo from Christchurch
Christchurch to Tekapo Small-Group Tour

Christchurch to Tekapo Small-Group Tour (one-way)

€100
per adult
Christchurch to Tekapo Small-Group Tour (one-way)
See all activities in Winchester

Frequently asked questions

How much does a Winchester holiday 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 holiday 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 holiday 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 holiday 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 holiday as a package?
Expedia holiday 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 holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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, favourite 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 accommodation, 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 personalised Winchester holiday package.

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.