Winchester Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Winchester Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Anaheim Rsrt - Conv Cntr
JW Marriott Anaheim Resort
Portofino Hotel & Marina
Clementine Hotel & Suites Anaheim
The Hollywood Roosevelt
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.

Top hotels in Winchester

Pala Casino Spa And Resort
Pala Casino Spa And Resort
4 out of 5
11154 Highway 76, Pala, CA
Fully refundableReserve now, pay when you stay
The price is S$305 per night from 28 Nov to 29 Nov
S$305
includes taxes & fees
28 Nov - 29 Nov
8.6/10 Excellent! (2,345 reviews)
"We had a great time here!"

Reviewed on 22 Nov,2024

Pala Casino Spa And Resort
Signature Temecula
Signature Temecula
3 out of 5
28980 Old Town Front St., Temecula, CA
Fully refundableReserve now, pay when you stay
The price is S$108 per night from 25 Nov to 26 Nov
S$108
includes taxes & fees
25 Nov - 26 Nov
8.4/10 Very Good! (1,363 reviews)
"Rooms have mini refrigerator and microwave."

Reviewed on 19 Nov,2024

Signature Temecula
Tahquitz Pines Retreat
Tahquitz Pines Retreat
2 out of 5
55251 S. Circle Dr, Idyllwild, CA
Fully refundableReserve now, pay when you stay
The price is S$112 per night from 8 Dec to 9 Dec
S$112
includes taxes & fees
8 Dec - 9 Dec
9.4/10 Exceptional! (556 reviews)
"Me and my gf fell in love with this place it’s cute nice and the staff are great an very helpful I will definitely be staying here again I’ve even recommended it to my friends and family"

Reviewed on 19 Nov,2024

Tahquitz Pines Retreat
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?
From as low as S$1,811. Yes, you read that correctly. Our Winchester holiday packages are a great way to stretch your budget further. Combine your hotels, flights and rental car and get to know this vibrant destination.
How do I get a cheap travel package to Winchester?
You’ll save big if you combine your flights, car rentals and hotels into a Winchester holiday package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 partner airlines and 1,000,000 properties globally, which means you’ll always have plenty of variety to choose from. Want to save even more? Add some popular activities to your package deal to unlock even more bargains! After all, travel is about more than just getting to your destination.
How far in advance should I book my Winchester holiday?
To bag cheap prices, book as soon as you can. Airlines typically release flights, along with some of the lowest fares, up to 12 months prior to departure. Hotels, experiences and car rental should also be booked early so you can have the pick of the bunch. If you’ve decided on a last-minute getaway in Winchester, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Winchester travel package include?
Hotels, flights and car rentals — we connect you to the very best deals. All you’ll have to do is figure out your preferred combination. Once you’ve made your booking, you can add on the exciting stuff like sightseeing activities. Our travel packages make it easy to create an unforgettable Winchester trip.
What should I know before booking a Winchester travel package?
You can save a tidy sum by combining your flights, hotels and rental cars. Once you’ve created your package, you can add on things like tours and activities. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Winchester Expedia holiday package?
With a holiday package, you’re the one in charge. Whether you’re hoping to fly to Winchester in economy or business class, simply choose from the available airline options. Expedia has access to over 550 airline partners globally.
If I'm not able to travel, can I cancel my Winchester holiday package?
Don’t stress if you’re rethinking your Winchester holiday package — you can cancel or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so head to our Customer Service Portal if that happens. When you’re ready to make changes, we’re ready to help.

* 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.