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.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,469
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (5,174 reviews)
Excellent location and well run. Staff very helpful and courteous.
Breakfast excellent too- no negatives found!
Would definitely recommend!
Reviewed on Sep 24, 2026
Pendry Chicago
Downtown Chicago
CA $922
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,146 reviews)
Property was clean. Staff was so lovely. Asked if special occasion and sent some drinks up. Overall great location and convenient. On the downside - noisy location also and difficult to get rooftop seating. It is not a bar rooftop. Flew into O’Hare and took subway and from there walked to hotel w one carry on suitcase.
Reviewed on Sep 23, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,257
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (561 reviews)
Great stay in an elegant mostly residential building. Smooth check in, but had to fill out a few forms. Very nice staff. Young building with lots of dogs yay!
Reviewed on Sep 24, 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 $127
CA $141 total
Oct 1 - Oct 2
includes taxes & fees
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
CA $115
CA $128 total
Oct 20 - Oct 21
includes taxes & fees
6/10 (337 reviews)
"Very dark, dingy, could smell people smoking cigarettes and weed in their rooms from the hallway. Very dated in the room with half assed repairs made. Bathroom door barely shut. I left after 2 hours and never returned."
Reviewed on Sep 16, 2026
Abbey Resort and Avani Spa
269 Fontana Boulevard Fontana WI
Fully refundableReserve now, pay when you stay
CA $144
CA $196 total
Oct 8 - Oct 9
includes taxes & fees
8.6/10 Excellent! (2,085 reviews)
"Beautiful location and great updating of facilities and restaurant. Nice to have a pool for kids and separate pool for adults only."
Reviewed on Sep 24, 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
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 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.
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.
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.
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.
Craig Woods Golf Club
7.4/10 (3 reviews)
Enjoy a round of golf in Woodstock at Craig Woods Golf Club. Amble around the area's lakeside or attend a sporting event.
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 $657 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.
