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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Convenient. Can stroll to locations within 30 mins. Train 4 blocks away, bus to riverwalk around the corner, restaurants, and the Mile a short walk away.

Reviewed on 14 Aug 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.

Reviewed on 12 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Oct - 2 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Beautiful views and incredibly clean environment. Perfect location for the lake, shopping, park, eating, you name it!

Reviewed on 14 Aug 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
per person
28 Oct - 2 Nov
found 1 day ago
Return direct flight included
Shannon (SNN) to Chicago (ORD)
9.4/10 Exceptional! (1,927 reviews)
Perfect stay! Great location

Reviewed on 13 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 17 Aug to 18 Aug
€85
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (917 reviews)
Great stay
"Great customer service, great breakfast, comfortable beds , awesome pool"

Reviewed on 12 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! (1,220 reviews)
"Wonderful AC. Relaxing pool time. Excellent location to lake, walking path, shopping, and restaurants."

Reviewed on 12 Aug 2025

Get rates
Harbor Shores on Lake Geneva
See all 1,161 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 €1,102 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.