Woodstock Holidays from £1,039
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Your Woodstock Holiday
With one of our holiday 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 holiday is easy with Expedia.
Top Woodstock Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
£1,039
per person
29 Sept - 3 Oct
found 24 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.
Reviewed on 17 Aug 2026
Kinzie Hotel
Downtown Chicago
£1,103
per person
25 Oct - 30 Oct
found 15 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (2,161 reviews)
Muy buen lugar pero personal debe ser más servicial y buscar la manera de que alguien ayude con el idioma español. Y no solo ignorar a los huéspedes.
Reviewed on 17 Aug 2026
Level Chicago Fulton Market
Downtown Chicago
£1,153
per person
1 Oct - 5 Oct
found 15 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on 12 Aug 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
£1,924
per person
26 Sept - 2 Oct
found 22 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.
Reviewed on 16 Aug 2026
Woodstock Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 25,200 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Petersen Park Beach, McHenry Shores Beach Park and Main Beach |
Top hotels in Woodstock
AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
£74
18 Aug - 19 Aug
includes taxes & fees
8/10 Very good! (1,005 reviews)
"The whole place was kind of smelly. Our room smelled like someone smoked in it before we got there. There was a dog in the room across the hall that was evidently left alone and was barking and whimpering until the owners came back about an hour later. The breakfast was inedible. Will not stay there ..."
Reviewed on 16 Aug 2026
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
£65
7 Sept - 8 Sept
includes taxes & 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 4 Aug 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
£129
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,387 reviews)
"We love this property and have stayed here many times over the years. The views are amazing and well worth the small amount you pay to be on the lake side of the building. I doubt that I would stay anywhere else. It’s always clean and the staff is always polite."
Reviewed on 17 Aug 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.
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 centre offers expert guidance on McHenry County's attractions. Explore interactive exhibits before planning your adventures.
Frequently asked questions
Why should I book my Woodstock holiday with Expedia?
With excellent-value airfares, car hire and hotel choices all in one place, Expedia makes planning your Woodstock break a piece of cake. What's more, we can help you bundle your bookings into a package holiday so you can save even more. Select from awesome properties, add flights and/or a hire car (and maybe also some fun tours!) and score incredible prices. Had a change of plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, visit our Customer Service Portal link.
When is the best time of year to holiday in Woodstock?
Peak season falls in June, July and August and is a thrilling time to visit — but be prepared for bigger crowds and longer queues. January, February and October are typically quieter times of the year. Organise your escape to Woodstock based on what type of adventure you want. January is the coolest time of year, when daytime temperatures average -6ºC. In July, the warmest month, you'll experience averages of 22ºC during the day.
What is the top hotel for my holiday in Woodstock?
Unwind in Woodstock by choosing LondonHouse Chicago, Curio Collection by Hilton as your home base and gateway to adventure and exploration.
How do I get a cheap holiday to Woodstock?
Browse and book everything in one place with our Woodstock holidays. We have incredible bargains on flights, hotels, tours and more that'll keep your wallet happy and your adventurous spirit alive. And, with more than 400 airlines and 321,000 hotel options worldwide to choose from, you'll have the flexibility to mix and match as you please. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Woodstock holiday?
Ensure your holiday in Woodstock is an unforgettable one by visiting its leading attractions. Crystal Lake Park, McHenry County Courthouse, Crystal Lake City Hall and Northwestern Medicine McHenry Hospital are among the things you should see while you're in the city.
What is the best area to stay in when on holiday in Woodstock?
There's so much to explore in Woodstock, so spend your nights close to its best sights and spend more time sightseeing. McHenry County Courthouse is one place to add to your to-do list.
Do I need a visa for my Woodstock holiday?
Official government websites have all the information you need on visa requirements, application procedures and necessary documentation. Your nationality and reason for your visit, whether it be for holidays or work, will determine if you need a visa for Woodstock. Be sure that your passport is up to date and has a minimum of six months validity remaining beyond your planned date of return. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Woodstock holiday?
First, think about the type of activities planned during your Woodstock trip and choose versatile pieces that can be mixed and matched. For fashion inspiration or even information on dress codes, look up a few style blogs or social media accounts. Daytime temperatures in January, Woodstock's coolest month, are around -6ºC. July marks this city's warmest month when average temperatures reach 22ºC. Our top piece of advice? Take the guesswork out of what to pack and check the weather forecast.
What does an Expedia Woodstock holiday include?
Hotels, flights and a shiny set of wheels for all your road trip adventures. Simply choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on some activities and tours and watch your savings pile up. When it comes to creating your Woodstock holiday, you're the one in control! Explore a wide range of property types and pick one that matches the size of your group. The most in-demand rentals here are private holiday homes and hotels. With Expedia, it's a breeze to tailor your Woodstock escape the way you like.
Does Expedia offer Book Now, Pay Later Woodstock holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a dream getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Consider one of these flexible payment options:
- Pay monthly holidays: If paying in multiple transactions works for you, Klarna offers just that! Paying in several transactions will make that dream getaway possible.
- No-deposit holidays: If not paying ahead of time for your trip makes pressing that "book now" button easier, consider a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!
Can I choose my airline with a Woodstock Expedia holiday?
Yes — and it's simple too. Expedia has access to more than 400 partner airlines throughout the world. Our holiday packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
