Woodstock Vacations from ￥446,202

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The Latest Woodstock Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Interstate Motel

Interstate Motel

2 out of 5
Price was ￥448,764, price is now ￥446,202 per person
￥446,202
per person
Jan 10 - Jan 13
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
7.4/10 Good! (22 reviews)
After making a reservation about two weeks in advance, we get there late in the evening to find out they do not have a room available that we reserved. Then, we reluctantly agreed to another room and the smoke smell was so strong. We went to the desk to ask for another room and were told they did not have any other rooms. We had to go to another establishment and find a room. Don’t waste your time.

Reviewed on Mar 28, 2026

Watseka 24 Inn & Suites

Watseka 24 Inn & Suites

2 out of 5
Price was ￥457,818, price is now ￥453,927 per person
￥453,927
per person
Jan 10 - Jan 13
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
7.4/10 Good! (362 reviews)

Find the Best Woodstock Vacation Packages

Woodstock Hotel Deals

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

3 out of 5
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
The price is ￥14,372 per night from Nov 22 to Nov 23
￥14,372
￥15,951 total
Nov 22 - Nov 23
includes taxes & fees
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 refundable
The price is ￥12,074 per night from Nov 22 to Nov 23
￥12,074
￥13,400 total
Nov 22 - Nov 23
includes taxes & fees
Quality Inn & Suites Woodstock near Lake Geneva
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
The price is ￥14,834 per night from Nov 29 to Nov 30
￥14,834
￥20,605 total
Nov 29 - Nov 30
includes taxes & fees
Abbey Resort and Avani Spa
See all 1,164 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.

Stay near popular Woodstock attractions

A historic building with a clock tower, a theater, and a street with cars and pedestrians.

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.
See properties

Frequently asked questions

How much does a Woodstock vacation package cost?
You'll find cheap prices from ￥446,202 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.