Woodstock Vacations from $156

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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.
Illinois Beach Hotel

Illinois Beach Hotel

2 out of 5
Save 100% on your flight
Price was $261, price is now $156 per person
$156
per person
Oct 30 - Nov 2
found 15 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (384 reviews)
I like the place, it is very quiet and safe, but the room requires better cleaning, the balcony was not clean and blinds need to be washed, anyhow i liked it.

Reviewed on Aug 21, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was $1,322, price is now $641 per person
$641
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on Aug 22, 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $596 per person
$596
per person
Nov 10 - Nov 16
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.

Reviewed on Aug 21, 2025

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $999, price is now $599 per person
$599
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,020 reviews)
Overall is good but 1 concern we encountered is there is a clicking sound in our room or near our room, that distracts my husband while sleeping.

Reviewed on Aug 24, 2025

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $621 per person
$621
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (3,059 reviews)
Loved the property, big size room and very cool decoration! Great location

Reviewed on Aug 22, 2025

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Discover the most popular places to visit in Woodstock

Highlighted in the movie Groundhog Day, also housed plays that featured famous actors Orson Welles and Paul Newman.

Woodstock Opera House

4.5/5(6 reviews)

You can enjoy a show at Woodstock Opera House during your trip to Woodstock. While you're in the area, stroll along the lakeside.

Woodstock Opera House

Woodstock Square

4/5(19 reviews)

You can find out about the history of Woodstock with a trip to Woodstock Square. While you're in the area, stroll along the lakeside.

Woodstock Square

Bull Valley Golf Club

5/5(1 review)

Enjoy a round of golf in Woodstock at Bull Valley Golf Club. While you're in the area, stroll along the lakeside.

Bull Valley Golf Club

Woodstock Hotel Deals

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

2.5 out of 5
990 Lake Avenue, Woodstock, IL
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $100 total per night from Aug 25 to Aug 26
$100 total
Aug 25 - Aug 26
Total with taxes and fees
7.8/10 Good! (928 reviews)
"The hotel overall felt safe and clean enough. A couple things I could tell was they re-used the room key card sleeves, and there was a killed spider stuck to the TV guide that nobody had noticed or cleaned up. The TV service they had indicated over 50 channels, only 1 worked. The hotel was smoke ..."

Reviewed on Aug 22, 2025

AmericInn by Wyndham Woodstock IL
Super 8 by Wyndham Woodstock

Super 8 by Wyndham Woodstock

2 out of 5
1220 Davis Rd, Woodstock, IL
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $77 total per night from Sep 16 to Sep 17
$77 total
Sep 16 - Sep 17
Total with taxes and fees
6.2/10 (511 reviews)
"Convenient to our destination. Room was clean and comfortable. Good bed."

Reviewed on Jul 29, 2025

Super 8 by Wyndham Woodstock
Quality Inn & Suites Woodstock near Lake Geneva

Quality Inn & Suites Woodstock near Lake Geneva

2.5 out of 5
1785 S Eastwood Dr, Woodstock, IL
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Aug 31 to Sep 1
$85 total
Aug 31 - Sep 1
Total with taxes and fees
5.8/10 (248 reviews)
"The sign in process was too long. 3pm check in and only 1 person at the front and there was 4 of us waiting to be checked in."

Reviewed on Aug 18, 2025

Quality Inn & Suites Woodstock near Lake Geneva
See all 1,151 properties in Woodstock
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.

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Frequently asked questions

How much does a Woodstock vacation package cost?
You'll find cheap prices from $156 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.