Winchester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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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 S$126 per night from 22 Jul to 23 Jul
S$126
22 Jul - 23 Jul
includes taxes & fees
7.8/10 Good! (790 reviews)
"Character hotel with a fantastic old style elevator"

Reviewed on 5 Jul, 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 S$111 per night from 31 Jul to 1 Aug
S$111
31 Jul - 1 Aug
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 30 Jun, 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
Fully refundableReserve now, pay when you stay
The price is S$148 per night from 31 Jul to 1 Aug
S$148
31 Jul - 1 Aug
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 29 Jun, 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 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.