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.
Holiday Inn Chicago O'Hare – Rosemont by IHG
CA $1,063
per person
Oct 2 - Oct 6
found 4 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,097 reviews)
The front desk staff were exceptional and went above and beyond to make our stay comfortable. They were friendly, attentive, and always willing to help. Their excellent service and warm hospitality truly made a difference. Highly recommended!
Reviewed on Aug 7, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,915
per person
Sep 14 - Sep 17
found 10 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Traveled with my partner, it felt romantic and we loved the view and all the nearby attractions. We were given a $10 credit to the restaurant but didn’t use them because we were too busy exploring the entire pier. There is no pool however the oak beach is nearby. The property felt safe although it was accessible to everyone, you had to use your room key to access the elevators. The pier closed at 10p to public so we had private access to the beautiful nighttime views. Make sure you wear walking shoes!! The only things that bothered us were, Stains on the floor and bench in our room, shower head had weak water flow, other than that it was an amazing stay!!! Definitely will be back with my children.
Reviewed on Aug 8, 2026
Ready to book your vacation to Woodstock?
Woodstock Hotel Deals
AmericInn by Wyndham Woodstock IL
990 Lake Avenue Woodstock IL
Fully refundableReserve now, pay when you stay
CA $124
CA $137 total
Aug 11 - Aug 12
includes taxes & fees
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
CA $111
CA $124 total
Sep 6 - Sep 7
includes taxes & fees
6/10 (328 reviews)
"The place hasn't had any quality to it in years. I wish i could post the pictures I've taken to show future customers. I rate this quality in a ZERO"
Reviewed on Aug 4, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
CA $187
CA $243 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,385 reviews)
"Helpful staff, ideal location, quiet hours"
Reviewed on Aug 6, 2026
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.
Stay near popular Woodstock attractions
Woodstock Opera House
8.2/10 (27 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.
McHenry County Courthouse
7.4/10 (8 reviews)
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.
Woodstock Square
8.4/10 (52 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.
Bull Valley Golf Club
8.8/10 (8 reviews)
Enjoy a round of golf in Woodstock at Bull Valley Golf Club. While you're in the area, stroll along the lakeside.
McHenry County Fairgrounds
8.8/10 (15 reviews)
Enjoy an outing to McHenry County Fairgrounds during your stay in Woodstock. While you're in the area, stroll along the lakeside.
Naturally McHenry County Visitor Center
Naturally McHenry County Visitor Center is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Discover the jazz scene and shops in this family-friendly area.
Emricson Park
7.4/10 (16 reviews)
Explore the great outdoors at Emricson Park, a lovely green space in Woodstock. While you're in the area, stroll along the lakeside.
Crystal Woods Golf Club
9.4/10 (3 reviews)
Enjoy a round of golf in Woodstock at Crystal Woods Golf Club. Amble around the area's lakeside or attend a sporting event.
Frequently asked questions
How much does a Woodstock vacation package cost?
Offering excellent value package deals from CA $786 on Expedia, you'll be thrilled with how little a vacation to Woodstock costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Woodstock?
If you'd like to book a cheap Woodstock vacation package, consider planning a trip in February, March and April. You'll typically find lower rates on accommodations and flights during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Woodstock?
When planning your Woodstock vacation, a few days will be enough to explore the highlights. Be sure to stop by Craig Woods Golf Club — it's one of the major attractions in this destination. If you want more adventure, think about basing yourself here and setting off on some day trips from Woodstock.
Is it worth booking a vacation package to Woodstock?
Whether you'd like to explore major sights like Woodstock Opera House and Old Courthouse Arts Centre on your Woodstock vacation, or coming for its excellent golfing, festivals and history, there's something for everyone here. With so much to experience, you'll quickly learn why so many travellers think Woodstock is a good vacation destination.
How to find the best Woodstock package deals?
Finding a cheap Woodstock package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most affordable Woodstock package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Woodstock vacation as a package?
You can enjoy significant savings on your next Woodstock retreat by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Woodstock?
If you have your Woodstock travel dates confirmed, book early to score some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Woodstock?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Woodstock.
- Plan your budget wisely: As well as the cost of your stay, you should factor in other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Woodstock.
- Decide your trip length: Think about how much time you want to spend discovering Woodstock. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a personalized Woodstock vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
