Winchester Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to ฿4,531 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Winchester

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 ฿3,005 per night from 30 Jul to 31 Jul
฿3,005
฿3,456 total
30 Jul - 31 Jul
includes taxes & fees
9.4/10 Exceptional! (120 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
The Grosvenor
The Grosvenor
3 out of 5
26 Cains Terrace, Timaru
Fully refundableReserve now, pay when you stay
The price is ฿3,199 per night from 6 Jul to 7 Jul
฿3,199
฿3,679 total
6 Jul - 7 Jul
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 12 Jun 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 ฿3,039 per night from 7 Jul to 8 Jul
฿3,039
฿3,495 total
7 Jul - 8 Jul
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 24 Jun 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 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.