Woodstock Vacations from $520

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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

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $923, price is now $520 per person
$520
per person
Feb 12 - Feb 15
found 7 hours ago
Roundtrip non-stop flight included
Dallas (DAL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Art Villa

Art Villa

5 out of 5
West Town
Price was $1,524, price is now $562 per person
$562
per person
Feb 5 - Feb 11
found 1 day ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $1,117, price is now $552 per person
$552
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in.

Reviewed on Nov 25, 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was $2,366, price is now $1,339 per person
$1,339
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The staff was amazing. Will be making a return stay.

Reviewed on Nov 30, 2025

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,053, price is now $601 per person
$601
per person
Feb 10 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (983 reviews)
The staff was very courteous and helpful. I stayed in a corner 2 bdrm unti. It was so spacious! The kitchen was stocked with allthe basic needs. Rooms were quiet, bed werecomfy. The furniture was a bit worn. The city skyline and lake views from our corner unit with floor to ceiling windows was incredible. It wasnan amazing stay. Cant wait to go back!

Reviewed on Nov 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

McHenry County Fairgrounds

Enjoy an outing to McHenry County Fairgrounds during your stay in Woodstock. While you're in the area, stroll along the lakeside.

McHenry County Fairgrounds

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
$76 nightly
The price is $85 total per night from Dec 2 to Dec 3
$85 total
Dec 2 - Dec 3
Total with taxes and fees
7.8/10 Good! (985 reviews)
Room was clean. Hotel was safe and quiet. Breakfast options were decent. I did not have any complaints.

Reviewed on Nov 26, 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
$58 nightly
The price is $64 total per night from Dec 30 to Dec 31
$64 total
Dec 30 - Dec 31
Total with taxes and fees
6/10 (531 reviews)
B

Reviewed on Oct 10, 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
$55 nightly
The price is $61 total per night from Dec 31 to Jan 1
$61 total
Dec 31 - Jan 1, 2026
Total with taxes and fees
5.8/10 (284 reviews)
Management was excellent, property inside was well cared for but outside is run down

Reviewed on Nov 5, 2025

Quality Inn & Suites Woodstock near Lake Geneva
See all 1,137 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 $520 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.