Woodstock Holidays from £1,072

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Your Woodstock Holiday

With one of our holiday packages to Woodstock, you'll discover countless opportunities for fun and adventure. There's so much to look forward to, including its rich history and spectacular views. If a sightseeing tour is on the cards during your trip to Woodstock, swing by well-known attractions like McHenry County College, McHenry County Fairgrounds and Bull Valley Golf Club. Don't put off visiting this destination any longer. The ultimate Woodstock holiday is only a few clicks away with Expedia.

The Latest Woodstock Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
28 Jun - 1 Jul
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Great view and environment

Reviewed on 23 May 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,130 reviews)
Great place to stay. Walkable from south shore train, restaurants and theaters

Reviewed on 19 May 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
We have a plenty staying at this hotel has the best locations and restaurant is so good

Reviewed on 13 May 2024

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,902 reviews)
Beautiful room. Staff was responsive to messaging. Bed was hard. Not much with coffee or creamer. Need a safe in room.

Reviewed on 24 May 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Very nice, clean, large rooms. Well-appointed. Hotel lobby very welcoming. Looked like a lovely outdoor dining patio, though I didn’t eat there.

Reviewed on 22 May 2024

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,138 reviews)
My room was clean and staff friendly.

Reviewed on 21 May 2024

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 helpful staff and the clean rooms in their reviews. ...
8/10 Very Good! (751 reviews)
Consistently satisfactory
"Loved the new blackout shades. Excellent customer service."

Reviewed on 14 May 2024

AmericInn by Wyndham Woodstock IL
Timber Ridge Lodge and Waterpark
Timber Ridge Lodge and Waterpark
3.5 out of 5
7020 Grand Geneva Way, Lake Geneva, WI
Stay at this 3.5-star spa aparthotel in Lake Geneva. Enjoy free parking, a full-service spa and a golf course. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (2,296 reviews)
"I love it! Great for families ❤️"

Reviewed on 21 May 2024

Timber Ridge Lodge and Waterpark
Abbey Resort and Avani Spa
Abbey Resort and Avani Spa
3.5 out of 5
269 Fontana Boulevard, Fontana, WI
Stay at this 3.5-star beach resort in Fontana. Enjoy free parking, a full-service spa and 2 restaurants. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (1,008 reviews)
"IT was nice and peacfeul in the property. Though the activities provided and for which we wanted to see - movies, were unavailable due to having a staff training in the theatre. We tried to request spa services for couples, but they were booked, they could only offer separate sessions, for which ..."

Reviewed on 21 May 2024

Abbey Resort and Avani Spa
See all 1,136 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

Image for Woodstock Opera House

Woodstock Opera House

5/5(2 reviews)

You can enjoy a show at Woodstock Opera House on your trip to Woodstock. While you're in the area, stroll along the lakeside.

Woodstock Opera House
Image for Woodstock Square

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
Image for McHenry County Fairgrounds

McHenry County Fairgrounds

Enjoy an outing to McHenry County Fairgrounds during your stay in Woodstock. While you're in the area, stroll along the lakeside.

McHenry County Fairgrounds

* 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.