Woodstock Trips (flight + hotel)

Photo by Erik Rowley

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Top hotels in Woodstock

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
The price is P5,141 per night from Aug 6 to Aug 7
P5,141
P5,706 total
Aug 6 - Aug 7
includes taxes & fees
7.8/10 Good! (907 reviews)
"Fan was loud in the bathroom. No towels by the pool. Beds were nice. Desk service was acceptable."

Reviewed on Jul 21, 2025

AmericInn by Wyndham Woodstock IL
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
The price is P4,322 per night from Aug 6 to Aug 7
P4,322
P4,796 total
Aug 6 - Aug 7
includes taxes & fees
6/10 (236 reviews)
"The property was very run down. The room smelled clean, beds were comfy and staff eas very nice!"

Reviewed on Jun 22, 2025

Quality Inn & Suites Woodstock near Lake Geneva
Harbor Shores on Lake Geneva

Harbor Shores on Lake Geneva

3.5 out of 5
300 Wrigley Dr, Lake Geneva, WI
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,206 reviews)
"Easy check in and out."

Reviewed on Jul 25, 2025

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Harbor Shores on Lake Geneva
See all 1,140 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.

Popular places to visit

Naturally McHenry County Visitor Center

Naturally McHenry County Visitor Center is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Discover the jazz scene and shops in this family-friendly area.

Naturally McHenry County Visitor Center

Frequently asked questions

How much does a Woodstock vacation package cost?
You'll find cheap prices 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?
If you're hoping to snag a cheap Woodstock vacation package, consider planning a trip in February, March and April. You'll typically find lower prices on flights and accommodations during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Woodstock?
When planning your Woodstock vacation, a handful of days will be enough to tour the top spots. Be sure to check out Old Courthouse Arts Center — it's one of the leading sights in this destination. If you're looking for more adventure, think about basing yourself here and heading off on some tours from Woodstock.
Is it worth booking a vacation package to Woodstock?
Whether you're looking to check out major attractions like Woodstock Opera House and Old Courthouse Arts Center on your Woodstock vacation, or coming for its great golfing, festivals and history, there's something for everyone here. With so many things to do, you'll soon discover why so many visitors think Woodstock is a good vacation destination.
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.
How to plan a trip to Woodstock?

  1. Choose the best time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to visit Woodstock.
  2. Plan your budget wisely: In addition to the cost of your hotel, you should factor in other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may crop up during your trip to Woodstock.
  3. Decide your trip length: Consider how long you want to spend discovering Woodstock. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Woodstock vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.