Woodstock Vacations from $389
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Your Woodstock Vacation
With one of our vacation packages to Woodstock, you'll discover infinite opportunities for excitement and adventure. There's tons to experience, including its rich history and spectacular views. You'll want to do some exploring during your trip to Woodstock. Make time for top attractions such as McHenry County College, McHenry County Courthouse and Woodstock Opera House. No matter your travel plans or the size of your budget, putting together the ultimate tailored Woodstock vacation is easy with Expedia.
The Latest Woodstock vacation packages
Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Downtown Chicago
Downtown Chicago
$389
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
7.6/10 Good! (2,711 reviews)
Affordable option less than a block off Michigan avenue. While it is an older property, the room was very clean, and the staff did an excellent job refreshing the room each morning. Our room was on the inside of the building and we heard NO city noise during the night. Easy access to the train and buses. Very good Thai restaurant right next door, as well as a small diner for breakfast. I would definitely stay here again!
Reviewed on Aug 11, 2026
The Whitehall Hotel, BW Premier Collection
Downtown Chicago
$596
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (3,933 reviews)
The Hotel is located in a great area. Unfortunately it’s an older hotel and you can hear others through the wall with the rooms next to yours. If your room is facing the street there is street noise. The room was clean a little dated as it’s an older hotel. The staff were super friendly and helpful. I would probably only stay here again if the other hotels in the area I normally stay at are not available which is why I ended up at the hotel.The bakery coffee place in the lobby was good. I didn’t utilize the restaurant.
Reviewed on Aug 11, 2026
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.
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.
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.
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.
Naturally McHenry County Visitor Center
Located in Woodstock's historic Old Courthouse, this visitor center offers expert guidance on McHenry County's attractions. Explore interactive exhibits before planning your adventures.
Woodstock Hotel Deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
$90 nightly
$100 total
Aug 12 - Aug 13
Total with taxes and fees
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
$80 nightly
$89 total
Sep 1 - Sep 2
Total with taxes and fees
6/10 (328 reviews)
"The place hasn't had any quality to it in years. I wish i could post the pictures I've taken to show future customers. I rate this quality in a ZERO"
Reviewed on Aug 4, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
$169 nightly
$191 total
Sep 7 - Sep 8
Total with taxes and fees
9.2/10 Wonderful! (1,390 reviews)
"The property is located right next to the lake and downtown, making everything in the downtown area easily accessible by walking. The property itself was lovely and well maintained. The outdoor pool was beautiful, although a little small. The indoor pool, however, was very small and crowded, and ..."
Reviewed on Aug 11, 2026
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.
Find the Best Woodstock Vacation Packages
Woodstock Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 25,200 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | McHenry Shores Beach Park, Petersen Park Beach and Main Beach |
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Frequently asked questions
How much does a Woodstock vacation package cost?
You'll find cheap prices from $389 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?
You can usually find lower rates and greater availability in January, February and October. Take a look at our cheap Woodstock vacation packages and you could land some great off-season deals.
How many days is enough for Woodstock?
Typically, a few days is enough for a Woodstock vacation. With a well-organized itinerary, you can see all the major sights including Emricson Park, as well as discover some hidden gems along the way.
Is it worth booking a vacation package to Woodstock?
Woodstock has everything you need for a memorable trip — golfing, festivals and history are just the start. Whether you want to check out attractions like Bull Valley Golf Club and McHenry County Fairgrounds, or take the path less traveled, you'll find plenty to explore on your Woodstock vacation.
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.
Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Your Woodstock getaway should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
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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.
