Woodstock Holidays from £956

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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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
11 Jun - 14 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (205 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 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
18 Jun - 21 Jun
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,896 reviews)
Nice hotel close to shopping and restaurants. Hotel restaurant breakfast buffet food was cold. Valet parking too expensive. Staff was nice and accommodating. Our floor was noisy with people partying on Friday night.

Reviewed on 8 May 2024

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
per person
18 Jun - 21 Jun
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (2,197 reviews)
Good service and cleaning , the hotel is close to all principal areas of the city.

Reviewed on 10 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
11 Jun - 13 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
Beautiful experience Top shelf everything This was my 4th stay here while visiting Chicago

Reviewed on 10 May 2024

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
11 Jun - 13 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
7.8/10 Good! (1,013 reviews)
The staff were very kind when we requested to extend our stay -they made sure we got the best value as well. The rooms are small but well maintained. Perfect for a small weekend trip!

Reviewed on 10 May 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
11 Jun - 14 Jun
Return direct flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,124 reviews)
Need more pillows in the room.

Reviewed on 10 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
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! (750 reviews)
"Wonderful staff, not bad location"

Reviewed on 20 Apr 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
Enjoy free parking, a full-service spa and a golf course. Our guests praise the helpful staff and the clean rooms in their reviews.
8.4/10 Very Good! (2,276 reviews)
"Very good customer service. Nice environment and great activities."

Reviewed on 5 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
Our guests praise the helpful staff and the clean rooms in their reviews.
8.2/10 Very Good! (1,001 reviews)
Nice place, does anybody work here?
"We go once or twice a year and enjoy the pool and scenery. The restaurant is good and the accommodations are nice. The furnishings seemed newer and everything worked in the room. I recommend the second floor (the first floor is more of a basement and has noise problems). This hotel always seems under-staffed. ..."

Reviewed on 4 May 2024

Abbey Resort and Avani Spa
See all 1,139 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.