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.
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Top hotels in Winchester

Quiet Couple's Retreat: Studio by Winchester Lake!
Quiet Couple's Retreat: Studio by Winchester Lake!
3 out of 5
Winchester
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Quiet Couple's Retreat: Studio by Winchester Lake!
Rustic Western Home: Walk to Winchester Lake!
Rustic Western Home: Walk to Winchester Lake!
3 out of 5
Winchester
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Rustic Western Home: Walk to Winchester Lake!
Cozy Winchester Lake Cabin: Hunting/fishing Haven!
Cozy Winchester Lake Cabin: Hunting/fishing Haven!
3 out of 5
Winchester
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Cozy Winchester Lake Cabin: Hunting/fishing Haven!
See all 23 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?
Cross off another part of the world with our Winchester holiday packages, which start from a low . Select the flights and hotels that match your travel plans. Then, add on a few tours or experiences to cap off your unique adventure.
How do I get a cheap travel package to Winchester?
If you love getting a great deal, combine your bookings into a Winchester holiday package. Whether you’re chasing flights, hotels, activities or rental cars, you can book them all in one place. You’ll have lots of choice at your fingertips as well. Expedia has over 550 partner airlines and 1,000,000 properties globally to take your pick of. Fly with who you want, stay anywhere you like and save a tidy sum — now that’s the ideal escape!
Where should I stay in Winchester?
If you’ll be visiting Winchester Lake State Park, forget about commuting and stay close by. It’s one of the most popular attractions in this area.
What are the top hotels in Winchester?
Whether you’ll be staying for one or several nights in Winchester, you’ll get a great night’s rest at Quiet Couple’s Retreat: Studio By Winchester Lake. This option is popular with many travellers.
How far in advance should I book my Winchester holiday?
Travellers are usually able to browse international airfares on Expedia up to 12 months prior to departure. Booking late? With a little bit of luck, it’s still possible to purchase an affordable ticket just weeks before your flight.
What does an Expedia Winchester travel package include?
Flights, hotels and rental cars — we’ve got them well covered. With Expedia, you can shape your Winchester travel package your way. All you have to do is work out exactly what you need. Once you’ve made your booking, you can add on fun things like tours and activities. The more you bundle, the greater your savings!
What should I know before booking a Winchester travel package?
So many places to wander around, so many things to see and do. With a travel package, you’ll be able to afford more of them. Bundle your flights, hotels and rental cars and enjoy big savings.
Can I choose my airline with a Winchester Expedia holiday package?
Definitely. Expedia has over 550 airline partners to select from globally. With all that choice at your fingertips, finding the ideal carrier to whisk you off to Winchester won’t be hard.
If I'm not able to travel, can I cancel my Winchester holiday package?
Your situation can change suddenly, so yes. You may be able to cancel and rebook your Winchester holiday package for free within 24 hours of booking. For bookings older than that, you can still cancel and rebook, but your airline, hotel or car rental company may charge a fee. Need more information? Take a look at our Customer Service Portal. We’ll help make sure your getaway goes off without a hitch.

* 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.