Woodstock Vacations from $383

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Your Woodstock Vacation

Experience the unique personality of Woodstock with a customized Woodstock vacation package. From its spectacular views to its rich history and beyond, you'll never have a boring moment in this city. Make your trip to Woodstock even more fun and exciting by including some sightseeing. McHenry County Fairgrounds, McHenry County College and McHenry County Courthouse are among the leading attractions you'll want to explore. Don't delay visiting this destination any longer. Your perfect Woodstock vacation is only a few clicks away with Expedia.

The Latest Woodstock Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,007 reviews)
Great location. Kind staff. Nice property.

Reviewed on May 1, 2024

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 16 - Jun 20
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (2,153 reviews)
Nice hotel close to everything

Reviewed on Apr 30, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun 4 - Jun 7
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 9 - Jul 13
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.8/10 Excellent! (206 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 Mar 16, 2024

JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 19 - Jul 21
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on Apr 14, 2024

Woodstock Essential Information

Language
English
Currency
U.S dollars
Population
25,200
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
McHenry Shores Beach Park, Petersen Park Beach and Main Beach

Woodstock Hotel Deals

AmericInn by Wyndham Woodstock IL
AmericInn by Wyndham Woodstock IL
2.5 out of 5
990 Lake Avenue, Woodstock, IL
Fully refundableReserve now, pay when you stay
The price is $90 per night from May 9 to May 10
$90
$100 total
includes taxes & fees
May 9 - May 10
8/10 Very Good! (750 reviews)
"Wonderful staff, not bad location"

Reviewed on Apr 20, 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
Fully refundableReserve now, pay when you stay
The price is $129 per night from May 7 to May 8
$129
$178 total
includes taxes & fees
May 7 - May 8
8.4/10 Very Good! (2,267 reviews)
"It was a great place for a little getaway for a family with a 5 year old. We will definitely go back again."

Reviewed on Apr 28, 2024

Timber Ridge Lodge and Waterpark
Hyatt Place Chicago/Hoffman Estates
Hyatt Place Chicago/Hoffman Estates
3 out of 5
2750 Greenspoint Pkwy, Hoffman Estates, IL
Fully refundable
The price is $83 per night from May 12 to May 13
$83
$94 total
includes taxes & fees
May 12 - May 13
8.4/10 Very Good! (1,003 reviews)
"We are not of Hispanic descent and would have liked to have a regular American breakfast like scrambled eggs, sausage, bacon, biscuits and/or sausage gravy & toast. We don’t eat tacos & scrambled eggs for breakfast. The employees were very nice & helpful."

Reviewed on Apr 25, 2024

Hyatt Place Chicago/Hoffman Estates
See all 1,133 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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Beach Vacations

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Frequently asked questions

How much does a Woodstock vacation package cost?
Perhaps less than you imagined — from just $383, in fact! By bundling hotels, flights and car rentals into your own tailor-made package, your trip to Woodstock is just clicks away.
How do I get a cheap travel package to Woodstock?
Combine your flight and hotel bookings, add extras such as tours, and save with a Woodstock vacation package. You won’t just enjoy big discounts on your escape — you’ll have loads of choice at your fingertips too. When you book with Expedia, you can select from more than 550 airlines and 1,000,000 properties worldwide. Your next epic adventure starts right here, right now!
Where should I stay in Woodstock?
Stay where the action happens. Many visitors like to book hotels around popular attractions, such as McHenry County Fairgrounds, Bull Valley Golf Club and Woodstock Opera House.
What are the top hotels in Woodstock?
If it’s your first visit to Woodstock, book a room at The Tailor House or Quality Inn & Suites Woodstock near Lake Geneva. Both offer comfy beds and are top options with many travelers.
How far in advance should I book my Woodstock vacation?
It can be tricky to know exactly when is the ideal time to book your trip to Woodstock. But typically the earlier you book, the cheaper the prices. Sometimes, you can secure your flights and hotels nearly a year before departure. If you’re eager to escape on a last-minute getaway, no need to stress! There are plenty of fantastic deals featured on Expedia every single day.
What does an Expedia Woodstock travel package include?
Packages include flights, rental cars and hotels, but you can mix and match them to create your ideal Woodstock trip. You can also add on a few tours and activities once you’ve made your booking. You’re in charge! When you combine your bookings with Expedia, you’ll get access to deals you won’t find elsewhere.
What should I know before booking a Woodstock travel package?
Tailor deals to suit your budget with an Expedia package. Hotels, airfares, rental cars — we’ve got everything you need to plan your getaway. You’ll save precious cash just for combining your bookings. Whether you’re going on a snow and ski adventure or sunning yourself on a warm beach, your dream vacation is just clicks away.
Can I choose my airline with a Woodstock Expedia vacation package?
Yes — that’s the beauty of an Expedia vacation package. You get to decide. We have more than 550 partner airlines all over the world, so you have options galore when putting together your Woodstock adventure.
If I'm not able to travel, can I cancel my Woodstock vacation package?
You can cancel your Woodstock booking if your travel plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Woodstock

Image for Woodstock Opera House

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
Image for Woodstock Square

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
Image for McHenry County Courthouse

McHenry County Courthouse

McHenry County Courthouse is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or attend a sporting event in this family-friendly area.

McHenry County Courthouse

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.