Woodstock Vacations from $503
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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.
The Emily Hotel
Downtown Chicago
$503
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,338 reviews)
Front desk staff was great as was housekeeping staff. Rooms were nothing special. Shower and bathroom floor had moldy grout. Bed was absolutely awful. Felt like sleeping on golfballs. Bar staff was awful. Wanted a quick drink while waiting for an Uber. Told them to charge to room. Bartender went MIA so we asked, what we assumed was a manager to ring us, he said ‘yep’ then went on to make some drinks, ignoring us. For the $$$ you can find much better hotels.
Reviewed on Sep 27, 2026
Level Chicago Fulton Market
Downtown Chicago
$976
per person
Nov 28 - Dec 4
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (573 reviews)
We enjoyed our stay. The apartment was spotless, and the kitchen was well-stocked with appliances and utensils. We loved the Nespresso machine! Our only disappointment was the nighttime noise from nearby trains, plus one night of loud partying below our rental. The staff was friendly and helpful. We recommend this property.
Reviewed on Sep 26, 2026
Level Chicago – Old Town
Downtown Chicago
$621
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
Amazing stay for a family of four. The kids loved the pool, and the adults loved the hot tub! It felt close to the action, without being too close. Quiet but walkable to Navy Pier, Michigan Avenue, etc. Nearby multiple grocery stores. The building was well maintained and the neighborhood felt safe. The views from the room were unbelievable (the pictures don't do them justice). I would definitely stay here again.
Reviewed on Sep 26, 2026
Stay near popular Woodstock attractions
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 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.
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.
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.
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.
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.
Woodstock Hotel Deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
$90 nightly
$100 total
Oct 4 - Oct 5
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
"The guy at desk dizzy was rude to my son and I. The toilet seat in room was broken the shower head was not good there were cracks in slings and tiles in bathrooms. There was an issue at pool another guest hit head and was bleeding as we left I made the guy at desk aware he acted like it was an inconvenience ..."
Reviewed on Sep 26, 2026
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
$82 nightly
$91 total
Oct 25 - Oct 26
Total with taxes and fees
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
$140 nightly
$155 total
Oct 8 - Oct 9
Total with taxes and fees
8.6/10 Excellent! (2,097 reviews)
"Food good at restaurant."
Reviewed on Sep 27, 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 $503 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.
