Winchester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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$105 per night from 11 Dec to 12 Dec
S$105
includes taxes & fees
11 Dec - 12 Dec
7.6/10 Good! (751 reviews)
Central hotel
"This hotel is very centrally located, which is handy if you come by coach. It is an older hotel that has been modernised."

Reviewed on 24 Nov,2024

The Grosvenor
Andorra Motel
Andorra Motel
3 out of 5
16 McKenzie St, Geraldine
Fully refundableReserve now, pay when you stay
The price is S$108 per night from 16 Dec to 17 Dec
S$108
includes taxes & fees
16 Dec - 17 Dec
9.6/10 Exceptional! (224 reviews)
"Just a really welcoming well cared for place."

Reviewed on 17 Nov,2024

Andorra 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$162 per night from 11 Dec to 12 Dec
S$162
includes taxes & fees
11 Dec - 12 Dec
9.4/10 Exceptional! (103 reviews)
"The hotel was amazing. Close to everything, the manager gave great advice on dinner, sight seeing, how to see the blue penguins. Clean, well equipped room with a great view of the water. Highly recommend"

Reviewed on 11 Nov,2024

Bay Viaduct Motor Lodge
See all 66 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?
Perhaps much less than you think — from a tempting , as a matter of fact! By combining flights, hotels and car rentals into a customized holiday package, your trip to Winchester is only clicks away.
How do I get a cheap travel package to Winchester?
Combine your bookings with Expedia to save on your next adventure. With more than 550 air carriers and 1,000,000 hotels across the world, your Winchester holiday package can be customized exactly to suit your budget. With all that extra money, why not include one or two interesting tours and experiences? It’s an easy way to unlock even more bargains. The holiday you’ve always dreamed of in Winchester is much closer than you thought!
How far in advance should I book my Winchester holiday?
Browse Expedia to compare international fares ASAP. You can usually purchase a ticket up to a year prior to departure. If you can’t find your preferred air carrier, or you’ve left things to the last moment, don’t worry. Cheap fares to Winchester occasionally appear just weeks before the date of departure.
What does an Expedia Winchester travel package include?
That depends on what you’re after. If you’re travelling solo, you might decide to combine hotels and flights. Taking the whole family to Winchester? A travel package that includes rental cars, flights and hotels might suit you better. Expedia gives you the flexibility and freedom to customize your travel package.
What should I know before booking a Winchester travel package?
You’ll enjoy excellent savings when you bundle your flights, hotels and rental cars into a package. Plus, booking everything in one spot just makes things easier. So why waste your time or money? Whether you’re organising an upscale romantic escape or a low-cost family road trip, take a look at our package deals today.
Can I choose my airline with a Winchester Expedia holiday package?
Yes, definitely. Expedia has more than 550 airline partners to pick from around the world. With all that choice, finding the perfect carrier to bring you to Winchester will be a snap.
If I'm not able to travel, can I cancel my Winchester holiday package?
We totally get it — sometimes life doesn’t go according to plan. If you’ve booked a Winchester holiday package and have to cancel or change it, we’re here to help. It’s always worth looking up our Customer Service Portal first for information. But generally, if you’ve booked your package within 24 hours, you may be able to cancel or change your itinerary at no cost. If it’s been more than 24 hours, your airline, hotel or car rental company may impose a charge.

* 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.