Woodstock Vacations from ￥305,598
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The Latest Woodstock Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥305,598
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
This is a very nice hotel. Beautifully decorated and very elegant. But, if you don't like using the hotel app on your phone to get things done, you may not like it. The rooms are big and comfortable, but the TV situation is a huge issue. I think they use wireless and a smart TV, but there is no way to change channels and the remote control is a real pain. There is no guide, but they have you use your phone to check see what the channels are, but there's no way to know what's on. If you want to use your streaming apps, it's another pain. I gave up.
However, the breakfast buffet is excellent and run with such efficiency it is really impressive. And the coffee in the room is good if you miss breakfast. There isn't any room service, but you can order on the app and go pick it up. Not great.
The location is a very busy spot which would make it seem great for taxis but not really. However it is so close to N. Michigan Ave that it doesn't really matter.
Reviewed on Sep 6, 2026
Find the Best Woodstock Vacation Packages
Woodstock Hotel Deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
￥14,062
￥15,606 total
Sep 13 - Sep 14
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"The staff was very welcoming when I arrived for my stay. It was a bit difficult to locate the property, due to placement and road construction, and parking was limited. However, the hotel made up for it with good amenitites"
Reviewed on Sep 3, 2026
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
￥12,745
￥14,145 total
Oct 4 - Oct 5
includes taxes & fees
6/10 (335 reviews)
"Only negative about our stay was there was not an elevator for the second floor rooms and they had booked all of their downstairs rooms. Pool was nice. It is a small pool and not very deep. Was perfect for the kids to play in. And for the adults relax in. Washer and dryer on site was a nice touch. ..."
Reviewed on Sep 6, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
￥19,325
￥25,396 total
Sep 7 - Sep 8
includes taxes & fees
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.
Stay near popular Woodstock attractions
Woodstock Opera House
8.2/10 (27 reviews)
This historic 1889 venue blends Victorian elegance with cultural significance as a "Groundhog Day" filming location. Experience performances surrounded by meticulously restored architectural details.
McHenry County Courthouse
7.4/10 (8 reviews)
McHenry County Courthouse is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or attend a sporting event in this family-friendly area.
Woodstock Square
8.4/10 (52 reviews)
This Victorian-era town square gained fame as the filming location for "Groundhog Day." Explore charming boutiques, then relax at the central gazebo where community events and live music often unfold.
McHenry County Fairgrounds
8.8/10 (15 reviews)
This venue hosts the vibrant McHenry County Fair each August, featuring livestock, carnival rides, and local culture. Year-round, visitors enjoy events from farmers markets to motorsport competitions.
Bull Valley Golf Club
8.8/10 (8 reviews)
Designed by Dick Nugent in 1989, Bull Valley Golf Club showcases rolling fairways and dramatic elevation changes on reclaimed farmland. The challenging layout requires strategic play through water hazards and bunkers.
Emricson Park
7.4/10 (16 reviews)
This 60-acre green haven features an inclusive playground and fitness court amid scenic wooded trails. Enjoy tennis, disc golf, or peaceful walks around the serene pond after exploring the park's natural beauty.
Craig Woods Golf Club
7.4/10 (3 reviews)
This serene 9-hole course features a challenging island green on its iconic third hole. Enjoy the mature trees and well-maintained fairways during a relaxing 2-hour round through Woodstock's picturesque landscape.
Crystal Woods Golf Club
9.4/10 (3 reviews)
This family-owned golf club features a thoughtfully designed 18-hole course with diverse challenges for all skill levels. The signature 12th hole offers an elevated tee shot and strategic pond placement near the green.
Frequently asked questions
How much does a Woodstock vacation package cost?
You'll find cheap prices from ￥305,598 on Expedia for your Woodstock getaway. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Woodstock costs.
What are the cheapest months to go to Woodstock?
If you're hoping to snag a cheap Woodstock vacation package, consider planning a trip in February, March and April. You'll typically find lower prices on flights and accommodations during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Woodstock?
When planning your Woodstock vacation, a handful of days will be enough to tour the top spots. Be sure to check out Old Courthouse Arts Center — it's one of the leading sights in this destination. If you're looking for more adventure, think about basing yourself here and heading off on some tours from Woodstock.
Is it worth booking a vacation package to Woodstock?
Whether you're looking to check out major attractions like Woodstock Opera House and Old Courthouse Arts Center on your Woodstock vacation, or coming for its great golfing, festivals and history, there's something for everyone here. With so many things to do, you'll soon discover why so many visitors think Woodstock is a good vacation destination.
How to find the best Woodstock package deals?
Start your search for a Woodstock package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Woodstock package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Woodstock escape underway.
Is it cheaper to book a Woodstock vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a personalized Woodstock vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Woodstock?
Land fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Woodstock escape.
How to plan a trip to Woodstock?
- Choose the best time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to visit Woodstock.
- Plan your budget wisely: In addition to the cost of your hotel, you should factor in other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Woodstock.
- Decide your trip length: Consider how long you want to spend discovering Woodstock. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Woodstock vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
