Woodstock Vacations from $244

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $424, price is now $244 per person
$244
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
There were no glasses in the room to drink out of. There was no lotion. There was no coffee maker. The shower curtain does not stretch the whole way so water gets all over the bathroom. We had a free VIP "hot" breakfast. When went down, there was no hot food. Just coffee and some bakery items. And no employee to serve us. Very, very misleading. We won't be staying here again.

Reviewed on Feb 2, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $654, price is now $353 per person
$353
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Modern Style Spacious Rooms with an Amazing complimentary breakfast every morning.

Reviewed on Feb 9, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Save 100% on your flight
Price was $637, price is now $373 per person
$373
per person
May 1 - May 4
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $989, price is now $593 per person
$593
per person
Apr 22 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Service was amazing and the location was perfect. Would definitely stay here again.

Reviewed on Jan 28, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $564, price is now $347 per person
$347
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on Feb 2, 2026

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Discover the most popular places to visit in Woodstock

Woodstock, Illinois - United States - April 8th, 2024: Exterior of the historical Old McHenry County Courthouse, built in 1857, in Woodstock, Illinois, USA.

McHenry County Courthouse

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.

McHenry County Courthouse
Street view in Woodstock Town of Illinois

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

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
$81 nightly
The price is $90 total per night from Feb 10 to Feb 11
$90 total
Feb 10 - Feb 11
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
I forgot my weighted pillow that is highly sentimental. We called and inquired about it. They promptly called back and are mailing it back to me. They were kind and compassionate!!

Reviewed on Feb 5, 2026

AmericInn by Wyndham Woodstock IL
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $153 total per night from Feb 15 to Feb 16
$153 total
Feb 15 - Feb 16
Total with taxes and fees
8.4/10 Very Good! (1,727 reviews)
The room is fine. Same for a resort. Just can’t understand why it was so cold everywhere?

Reviewed on Feb 2, 2026

Abbey Resort and Avani Spa
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

3.5 out of 5
7020 Grand Geneva Way Lake Geneva WI
Fully refundableReserve now, pay when you stay
$194 nightly
The price is $216 total per night from Feb 10 to Feb 11
$216 total
Feb 10 - Feb 11
Total with taxes and fees
8.6/10 Excellent! (3,130 reviews)
Great stay. First family trip with my little girl who is 2yr old and she loved here water park, whirlpool bath! We will come back again ;) btw staffs are so nice👍

Reviewed on Feb 3, 2026

Timber Ridge Lodge and Waterpark
See all 1,156 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.

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 $244 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.