Winchester Vacation Packages

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Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
per person
Jul. 4 - Jul. 8
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.8/10 Excellent! (1,271 reviews)
I always enjoy our stays at the Wildwood Hotel. All Staff members are friendly.

Reviewed on May 9, 2024

HoteLumiere at the Arch

HoteLumiere at the Arch

4 out of 5
Downtown St. Louis
per person
Jun. 28 - Jul. 1
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
6.8/10 (1,000 reviews)
Property was clean easy in and out. Elevator was broken and evidently has been. Overall great experience

Reviewed on Apr. 21, 2024

The Pennywell St.Louis Downtown, a Hilton Hotel

The Pennywell St.Louis Downtown, a Hilton Hotel

4 out of 5
Downtown St. Louis
per person
Jun. 28 - Jul. 1
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.8/10 Excellent! (350 reviews)
Hotel is cleverly converted from a former bank building with the vault still visible in the lobby serving as an entrance to the store.

Reviewed on May 7, 2024

Courtyard by Marriott St. Louis Downtown/Convention Center

Courtyard by Marriott St. Louis Downtown/Convention Center

3 out of 5
Downtown St. Louis
per person
Jun. 28 - Jul. 1
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9/10 Wonderful! (1,000 reviews)
Great location. Great service. Really nice lobby and bar area on the first floor. Nice and spacious room. I even had a nice view of the river and the old St Louis Rams football stadium. St Louis is on the up again. I felt very safe walking around a very clean downtown. Even at night.

Reviewed on Apr. 30, 2024

The Westin St. Louis

The Westin St. Louis

4.5 out of 5
Downtown St. Louis
per person
Jun. 28 - Jul. 1
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.4/10 Very Good! (1,005 reviews)
The building exterior is very industrial but the interior is just about the typical Westin loo. It is located adjacent to the Cardinals baseball stadium but the area is very quiet which is very refreshing. The staff are exceptionally friendly and they strive to provide the service I have come to expect at the Westin. I did note all Westins are not created equal so some simple amenities were missing; for example no bath mats were available, so I had to use a towel to stand on when exiting the shower. I prefer not to use the same towel I use to dry with to place on the floor. I noted a safety issue in the room which I reported and expect it will be fixed so no one gets injured. The lighting down the hallways on the occupied floors should be a little brighter as the hallways can be a long spooky walk from the elevator to the room depending. on your room location. The staff are exceptionally nice and friendly so I did enjoy my stay and would do so again.

Reviewed on May 3, 2024

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
See all 39 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.