Woodstock Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
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.
Swissotel - Chicago
Downtown Chicago
CA $1,315
per person
Oct 22 - Oct 26
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
The hotel is in a great area but the hotel itself was okay. Employees were nice and there are two nice bars in the hotel. My main issue is it did not get cold in my room even though I had the thermostat on the coldest setting. Also a bummer that there’s no pool.
Reviewed on Sep 7, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $2,117
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The rooms need to be updated. The room service and bell man took longer than we expected for a Four Seasons. There needs to be someone right when you walk in to direct new guests. We usually stay at the Peninsula Hotel. We wanted to try the Four Seasons but we will go back to the Peninsula Hotel going forward. We got the same type of suite but the bathroom and closet for a family of four was less than desirable. The bar at the hotel had great service! Great selection of upscale bar food. I was very happy about that service! I will say everyone was pleasant and accommodating! The wait times and the lack of attention for need to be compared to the Peninsula.
Reviewed on Sep 7, 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 $123
CA $136 total
Oct 6 - Oct 7
includes taxes & fees
8/10 Very good! (1,002 reviews)
"The staff was very welcoming when I arrived for my stay. It was a bit difficult to locate the property, due to placement and road construction, and parking was limited. However, the hotel made up for it with good amenitites"
Reviewed on Sep 3, 2026
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
CA $113
CA $125 total
Oct 4 - Oct 5
includes taxes & fees
6/10 (335 reviews)
"Only negative about our stay was there was not an elevator for the second floor rooms and they had booked all of their downstairs rooms. Pool was nice. It is a small pool and not very deep. Was perfect for the kids to play in. And for the adults relax in. Washer and dryer on site was a nice touch. ..."
Reviewed on Sep 6, 2026
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Fully refundableReserve now, pay when you stay
CA $171
CA $225 total
Sep 13 - Sep 14
includes taxes & fees
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.
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.
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.
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.
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 $1,287 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.
