Winchester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
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    Better together
    Save up to CA $775 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
HoteLumiere at the Arch
The Pennywell St.Louis Downtown, a Hilton Hotel
Courtyard by Marriott St. Louis Downtown/Convention Center
The Westin St. Louis

Winchester Hotel Deals

Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from May 19 to May 20
CA $122
CA $135 total
includes taxes & fees
May 19 - May 20
9.2/10 Wonderful! (380 reviews)
"Clean and organized"

Reviewed on May 7, 2024

Sleep Inn & Suites
Best Western Jacksonville Inn
Best Western Jacksonville Inn
2.5 out of 5
1709 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from May 12 to May 13
CA $96
CA $109 total
includes taxes & fees
May 12 - May 13
8.4/10 Very Good! (535 reviews)
One night stay
"Our stay was okay. Breakfast was awful. We were there for one night for a baseball tournament. The pool was so crowded we didn't get a chance to use it. The room itself was comfortable but small."

Reviewed on Apr. 7, 2024

Best Western Jacksonville Inn
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
2.5 out of 5
2501 Holliday Lane, Jacksonville, IL
Fully refundable
The price is CA $116 per night from May 26 to May 27
CA $116
CA $129 total
includes taxes & fees
May 26 - May 27
7.8/10 Good! (336 reviews)
"We had a major issue with my mother's room and the manager took action and took care of it. We appreciate it!"

Reviewed on Apr. 11, 2024

Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
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.

Explore other types of vacation packages

Frequently asked questions

How much does a Winchester vacation package cost?
Live it up in Winchester from just CA $1,012. We offer a wonderful selection of flights, rental cars and hotels to suit your travel style. Land even more discounts when you add a few sightseeing tours to your package.
How do I get a cheap travel package to Winchester?
Secure flights that fit your schedule, add a hotel room to your booking and watch the savings grow with a Winchester vacation package. It’s as simple as that! From hotels and flights to rental cars and tours, Expedia is where your cheap getaway begins. And with over 550 air carriers and 1,000,000 hotels all over the world to pick from, you’ll never be short of choice.
How far in advance should I book my Winchester vacation?
You’ll be rewarded with the biggest variety at the cheapest prices by booking your Winchester vacation nice and early. Air carriers usually advertise tickets around 12 months before departure, so reserve your spot ASAP. That being said, Expedia is committed to giving you the best bargains around, so it’s never a bad time to book your dream vacation!
What does an Expedia Winchester travel package include?
Rental cars, flights and hotels — you’ll discover them all here. With Expedia, you can create your Winchester travel package just how you like it. All you have to do is work out just what you need. Once you’ve made your booking, you can add extras like activities and tours. The more you bundle, the bigger the savings!
What should I know before booking a Winchester travel package?
Our prices are always low. However, you’ll grab an even better deal when you book your flights, hotels and car rentals together. With an Expedia package, you’ll get transparent pricing and a huge range of choice.
Can I choose my airline with a Winchester Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you sure can! Just select your favorite carrier and create the perfect Winchester vacation.
If I'm not able to travel, can I cancel my Winchester vacation package?
We get that life can throw you the odd curveball. If you’ve booked a Winchester vacation package and have to change or cancel it, we can help. We suggest browsing our Customer Service Portal first for information. But generally, if you’ve taken out your package within 24 hours, you may be able to cancel or amend your itinerary at no cost. If it’s been more than 24 hours, your hotel, airline 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.