Woodstock Holidays from £1,022

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Your Woodstock Holiday

With one of our holiday packages to Woodstock, you'll discover infinite opportunities for excitement and adventure. There's tons to experience, including its rich history and spectacular views. You'll want to do some exploring during your trip to Woodstock. Make time for top attractions such as McHenry County College, McHenry County Courthouse and Woodstock Opera House. No matter your travel plans or the size of your budget, putting together the ultimate tailored Woodstock holiday is easy with Expedia.

The Latest Woodstock Holiday Deals

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
7 Sept - 13 Sept
found 23 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
It’s in a great location and a lot of food spots nearby! The only thing I dislike you have to verbally request cleaning and room service but they don’t tell you that.

Reviewed on 29 Jun 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
12 Aug - 17 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
Excellent staff that were helpful, friendly and fun with our young children

Reviewed on 28 Jun 2025

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (678 reviews)
Great location. The service level was nowhere near a 5 star.

Reviewed on 26 Jun 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
7 Sept - 13 Sept
found 23 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,034 reviews)
I would recommend this hotel. Overall a good experience. Beautiful property, location and restaurant. I stayed Sunday into Monday and found Starbucks located a few blocks away a good choice for coffee in the morning. Early morning coffee should be easy.

Reviewed on 23 Jun 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
12 Aug - 17 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Location location location and this hotel is in the middle of everything love it

Reviewed on 29 Jun 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
per person
1 Aug - 6 Aug
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
Amazing service!! Beautiful hotel!

Reviewed on 22 Jun 2025

Woodstock Essential Information

Language
English
Currency
U.S dollars
Population
25,200
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Petersen Park Beach, McHenry Shores Beach Park and Main Beach

Our pick of the best Woodstock Hotel Deals

AmericInn by Wyndham Woodstock IL
AmericInn by Wyndham Woodstock IL
2.5 out of 5
990 Lake Avenue, Woodstock, IL
Stay at this ski hotel in Woodstock. Enjoy free breakfast, free parking and a casino. Our guests praise the clean rooms in their reviews. Popular attractions ...
7.8/10 Good! (893 reviews)
"Loved the Breakfast and the Room. Staff were friendly, an added plus."

Reviewed on 24 Jun 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
Stay at this business-friendly hotel in Woodstock. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
6/10 (229 reviews)
"The property was very run down. The room smelled clean, beds were comfy and staff eas very nice!"

Reviewed on 22 Jun 2025

Quality Inn & Suites Woodstock near Lake Geneva
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Stay at this 3-star business-friendly hotel in Hoffman Estates. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,000 reviews)
"Pleasant stay. Hotel is a bit dated and in need of some upgrades."

Reviewed on 25 Jun 2025

Hyatt Place Chicago/Hoffman Estates
See all 1,142 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Woodstock holiday with Expedia?
With excellent-value airfares, car hire and hotel choices all in one place, Expedia makes planning your Woodstock break a piece of cake. What's more, we can help you bundle your bookings into a package holiday so you can save even more. Select from awesome properties, add flights and/or a hire car (and maybe also some fun tours!) and score incredible prices. Had a change of plans? Expedia offers a flexible cancellation policy for many bookings. To find out more, visit our Customer Service Portal link.
When is the best time of year to holiday in Woodstock?
Peak season falls in June, July and August and is a thrilling time to visit --- but be prepared for bigger crowds and longer queues. January, February and October are typically quieter times of the year. Organise your escape to Woodstock based on what type of adventure you want. January is the coolest time of year, when daytime temperatures average -6ºC. In July, the warmest month, you'll experience averages of 22ºC during the day.
What is the top hotel for my holiday in Woodstock?
Unwind in Woodstock by choosing LondonHouse Chicago, Curio Collection by Hilton as your home base and gateway to adventure and exploration.
How do I get a cheap holiday to Woodstock?
Browse and book everything in one place with our Woodstock holidays. We have incredible bargains on flights, hotels, tours and more that'll keep your wallet happy and your adventurous spirit alive. And, with more than 400 airlines and 321,000 hotel options worldwide to choose from, you'll have the flexibility to mix and match as you please. Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Woodstock holiday?
Ensure your holiday in Woodstock is an unforgettable one by visiting its leading attractions. Crystal Lake Park, McHenry County Courthouse, Crystal Lake City Hall and Northwestern Medicine McHenry Hospital are among the things you should see while you're in the city.
What is the best area to stay in when on holiday in Woodstock?
There's so much to explore in Woodstock, so spend your nights close to its best sights and spend more time sightseeing. McHenry County Courthouse is one place to add to your to-do list.
Do I need a visa for my Woodstock holiday?
Official government websites have all the information you need on visa requirements, application procedures and necessary documentation. Your nationality and reason for your visit, whether it be for holidays or work, will determine if you need a visa for Woodstock. Be sure that your passport is up to date and has a minimum of six months validity remaining beyond your planned date of return. Finalise all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Woodstock holiday?
First, think about the type of activities planned during your Woodstock trip and choose versatile pieces that can be mixed and matched. For fashion inspiration or even information on dress codes, look up a few style blogs or social media accounts. Daytime temperatures in January, Woodstock's coolest month, are around -6ºC. July marks this city's warmest month when average temperatures reach 22ºC. Our top piece of advice? Take the guesswork out of what to pack and check the weather forecast.
What does an Expedia Woodstock holiday include?
Hotels, flights and a shiny set of wheels for all your road trip adventures. Simply choose your preferred bundle and gain access to great discounts. Once you've made your booking, add on some activities and tours and watch your savings pile up. When it comes to creating your Woodstock holiday, you're the one in control! Explore a wide range of property types and pick one that matches the size of your group. The most in-demand rentals here are private holiday homes and hotels. With Expedia, it's a breeze to tailor your Woodstock escape the way you like.
Does Expedia offer Book Now, Pay Later Woodstock holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a dream getaway without eating away at your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying in multiple transactions works for you, Klarna offers just that! Paying in several transactions will make that dream getaway possible.
  • No-deposit holidays: If not paying ahead of time for your trip makes pressing that "book now" button easier, consider a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Woodstock Expedia holiday?
Yes --- and it's simple too. Expedia has access to more than 400 partner airlines throughout the world. Our holiday packages give you the flexibility to take your pick of available flights, hotels and activities that suit you.

Discover the most popular places to visit in Woodstock

Woodstock Square

5/5(2 reviews)

You can find out about the history of Woodstock when you stop by Woodstock Square. While you're in the area, stroll along the lakeside.

Woodstock Square

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.