Deals on vacations and trips to Woodstock

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Popular places to visit

Highlighted in the movie Groundhog Day, also housed plays that featured famous actors Orson Welles and Paul Newman.

Woodstock Opera House

4.5/5(6 reviews)

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

Woodstock Opera House

Woodstock Square

4/5(19 reviews)

You can find out about the history of Woodstock with a trip to Woodstock Square. While you're in the area, stroll along the lakeside.

Woodstock Square

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

Frequently asked questions

How much are vacation packages to Woodstock?
With a Travelocity vacation package, you can live it up in Woodstock from just . Hotels, flights and experiences --- we have everything you need. You'll save a bunch just for bundling together your bookings. And with all that taken care of before leaving, you can sit back, relax and enjoy the adventure.
How long should my Woodstock vacation be?
Around 2 nights is the average time frame visitors vacation in Woodstock. But how long is right for you depends on how many magical memories you want to make. Why not stay a bit longer and uncover some of the lesser-known sights?
Where can I get the best vacation package deals for Woodstock?
Check out Travelocity. With access to 400 airlines and a massive 1,000,000 properties around the world, selecting the ultimate Woodstock package deal couldn't be simpler.
Why should I purchase my Woodstock vacation bundle with Travelocity?
Travel should be about making fantastic new memories and leaving all your worries behind --- which is why we provide you with a team of experts on hand around-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our impressive range of vacation destinations. So what are you waiting for? There's no time like the present to lock in the vacation you've always dreamed of.
Can I save money on my Woodstock car rental if I book it with hotels and flights?
You sure can --- combine your flight, car and hotel into a Woodstock vacation package and you'll save a tidy sum. With so much to uncover in and around Woodstock, that rental car will make exploring a breeze. Once you've buckled up, turn up the tunes and head to Wrigley Field, a top sight around 50 mi from Woodstock.
Which airport is best for Woodstock?
There's a very good chance you'll touch down at O'Hare Intl. Airport (ORD), located 35 mi southeast of downtown Woodstock. Midway Intl. Airport (MDW) (50 mi away from central Woodstock) and General Mitchell Intl. Airport (MKE) (50 mi away from central Woodstock) are your other choices.
What is there to do in Woodstock?
There is a particular magic in the air as you stroll through the streets of Woodstock. Woodstock Opera House and Old Courthouse Arts Center are just a couple of famous sights that entice visitors to this wonderful city, so put them at the top of your list of places to see.
Where should I stay when visiting Woodstock?
If you're searching for someplace comfortable to base yourself, take a look at the AmericInn by Wyndham Woodstock IL. It's the top choice for many travelers.

Photos of local treasures

Browse Woodstock vacation photos for more inspiration

Photo by Erik Rowley
Photo by Erik Rowley
Photo by Erik Rowley
Photo by Erik Rowley