Woodstock Holidays

Photo by Erik Rowley

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Top Flight + Hotel Deals in Woodstock

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €946, price is now €630 per person
€630
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone was wonderful and the property and rooms are very well maintained. Will definitely stay there again.

Reviewed on 24 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,932, price is now €1,162 per person
€1,162
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was €1,430, price is now €872 per person
€872
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) 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 22 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €1,979, price is now €1,240 per person
€1,240
per person
2 Nov - 7 Nov
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was €1,206, price is now €796 per person
€796
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Everything was nice!!

Reviewed on 23 Aug 2025

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 €85 per night from 25 Aug to 26 Aug
€85
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (926 reviews)
"Everything was good, just my key was not working everytime I returned to my room."

Reviewed on 19 Aug 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
The price is €66 per night from 22 Sept to 23 Sept
€66
22 Sept - 23 Sept
includes taxes & fees
6.2/10 (511 reviews)
"Convenient to our destination. Room was clean and comfortable. Good bed."

Reviewed on 29 Jul 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
The price is €72 per night from 26 Aug to 27 Aug
€72
26 Aug - 27 Aug
includes taxes & 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 18 Aug 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.

Popular places to visit

Crystal Woods Golf Club

Enjoy a round of golf in Woodstock at Crystal Woods Golf Club. Amble around the area's lakeside or attend a sporting event.

Crystal Woods Golf Club

Frequently asked questions

How much does a Woodstock holiday package cost?
You'll find cheap prices from €630 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 holiday to Woodstock costs.
What are the cheapest months to go to Woodstock?
If you're hoping to snag a cheap Woodstock holiday package, consider planning a trip in February, March and April. You'll typically find lower prices on flights and accommodation during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Woodstock?
When planning your Woodstock holiday, a handful of days will be enough to tour the top spots. Be sure to check out Old Courthouse Arts Centre — 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 holiday package to Woodstock?
Whether you're looking to check out major attractions like Woodstock Opera House and Old Courthouse Arts Centre on your Woodstock holiday, 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 holiday 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 holiday as a package?
Expedia holiday 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 personalised Woodstock holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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, favourite 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 personalised Woodstock holiday package.

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