Woodstock Holidays

Photo by Erik Rowley

Top Flight + Hotel Deals in Woodstock

Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
My husband and I stayed at The Allegro for a weekend getaway to celebrate our anniversary. It was my husband’s first time in Chicago and we could not have asked for a better stay. The location is perfect and the staff is amazing. We had a late flight after the 11am check-out time and the hotel let us check our bags for a few hours so we could fit in a little more exploration before heading home. We will definitely be visiting again!

Reviewed on 16 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Lovely rooms and staff very friendly and helpful.

Reviewed on 15 Aug 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (335 reviews)
Great property. Outstanding all the way around.

Reviewed on 13 Aug 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
so I gotta say The royal sonesta river north in particular is amazing it feels more like a hotel, it feels like a small community and all the staff and guest know each other. The front desk woman Gabby is amazing and dope as heck. Shaunda is a travel guide there, shes hilarious and gave us wonderful recommendations in the area. Antwonne is a dope Bellman great service and attitude. Every detail was perfect Jessenia apart of the housekeeping staff has such good attention to detail when it came to fixing up and cleaning the room everything was so organized and neat. Now to the room it couldn't have been more perfect they upgraded us to the luxury suite and it was beautiful (use the tub as much as you can)

Reviewed on 15 Aug 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Peninsula is simply the best. Top notch service, amenities and everything in between.

Reviewed on 14 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 18 Aug to 19 Aug
€85
18 Aug - 19 Aug
includes taxes & fees
7.8/10 Good! (919 reviews)
"Very convenient and relaxing for our family trip."

Reviewed on 15 Aug 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 €73 per night from 24 Aug to 25 Aug
€73
24 Aug - 25 Aug
includes taxes & fees
5.8/10 (245 reviews)
"Outside not well kept. But room was clean"

Reviewed on 6 Aug 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! (1,213 reviews)
"Location is perfect. Lake Geneva is not a place to be using the car, everything is walking distance, so this hotel by the lake and main walking area was perfect for us. It was surprisingly quiet for the location, we have a 3 year old so that worked out pretty well. Highly recommended."

Reviewed on 15 Aug 2025

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Harbor Shores on Lake Geneva
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.

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 €569 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.