Woodstock Vacation Packages

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Your Woodstock Vacation

With one of our vacation 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 vacation is easy with Expedia.

Top Woodstock Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
per person
Jul. 2 - Jul. 6
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
This was a really nice hotel in a great area with tons of restaurants, well lit up streets and easy walking in the downtown River North area. The hotel itself was lively on the ground floor with its bar and restaurant and the room was clean and well laid out and quiet overall The bed/pillows were really, really comfortable. I would stay here again anytime.

Reviewed on May 18, 2024

Millennium Knickerbocker Chicago

Millennium Knickerbocker Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 20
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
7.8/10 Good! (1,743 reviews)
Just overall a really nice place

Reviewed on May 22, 2024

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 2 - Jul. 6
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
EXCEPTIONAL SERVICE!!

Reviewed on May 21, 2024

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 14 - Aug. 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.2/10 Very Good! (1,509 reviews)
Balcony views were great! Staff was friendly and the room was a decent size. The only thing I would say needs improvement would be the cleanliness of the rooms and bathroom.

Reviewed on May 23, 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug. 15 - Aug. 20
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.8/10 Excellent! (1,018 reviews)
Everything was awesome.

Reviewed on May 19, 2024

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 CA $123 per night from May 26 to May 27
CA $123
CA $137 total
includes taxes & fees
May 26 - May 27
8/10 Very Good! (753 reviews)
Consistently satisfactory
"Loved the new blackout shades. Excellent customer service."

Reviewed on May 14, 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 CA $219 per night from Jun. 24 to Jun. 25
CA $219
CA $289 total
includes taxes & fees
Jun 24 - Jun 25
8.4/10 Very Good! (2,297 reviews)
"I love it! Great for families ❤️"

Reviewed on May 21, 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
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from May 27 to May 28
CA $197
CA $240 total
includes taxes & fees
May 27 - May 28
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 May 21, 2024

Abbey Resort and Avani Spa
See all 1,140 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Woodstock vacation package cost?
Perhaps less than you imagined — from just CA $674, 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

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

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 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

Other vacations you might like

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