Woodstock Holidays from £1,000

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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.

Top Woodstock Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was £1,282, price is now £1,000 per person
£1,000
per person
14 Aug - 18 Aug
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
The staff was very friendly and the location was great!

Reviewed on 2 Jul 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was £1,670, price is now £1,295 per person
£1,295
per person
14 Aug - 18 Aug
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.

Reviewed on 2 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,629, price is now £1,268 per person
£1,268
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very close to shopping, eating, and interstate. Great location. We walked to most of what we wanted to do.

Reviewed on 2 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,885, price is now £1,475 per person
£1,475
per person
14 Aug - 18 Aug
found 5 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service

Reviewed on 30 Jun 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,319, price is now £1,035 per person
£1,035
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
Great place!

Reviewed on 2 Jul 2026

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

Top hotels in Woodstock

AmericInn by Wyndham Woodstock IL

AmericInn by Wyndham Woodstock IL

3 out of 5
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
The price is £75 per night from 5 Jul to 6 Jul
£75
5 Jul - 6 Jul
includes taxes & fees
8/10 Very good! (1,002 reviews)
"It was a perfect to stay for a week. Perfect amount of cleanliness and quietness. Breakfast was adequate and got the job done. It worked perfectly for my family and I."

Reviewed on 1 Jul 2026

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 refundable
The price is £65 per night from 23 Jul to 24 Jul
£65
23 Jul - 24 Jul
includes taxes & fees
6/10 (320 reviews)
"We planned to stay here for the night as we were attending a wedding 20 minutes north. We ended up NOT STAYING at this hotel. The staff originally put us in a room and we opened the door and there was an entire family staying there. The one staff member said “maybe they never checked out,” but it ..."

Reviewed on 1 Jul 2026

Quality Inn & Suites Woodstock near Lake Geneva
Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
The price is £156 per night from 28 Jul to 29 Jul
£156
28 Jul - 29 Jul
includes taxes & fees
8.6/10 Excellent! (1,917 reviews)
"."

Reviewed on 2 Jul 2026

Abbey Resort and Avani Spa
See all 1,176 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

Stay near popular Woodstock attractions

A historic building with a clock tower, a theater, and a street with cars and pedestrians.

Woodstock Opera House

8.2/10 (27 reviews)
This historic 1889 venue blends Victorian elegance with cultural significance as a "Groundhog Day" filming location. Experience performances surrounded by meticulously restored architectural details.
See properties

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.

Explore a world of travel with Expedia

* 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.