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.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,271
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
My Labor Day weekend stay at Trump International Hotel & Tower Chicago was exceptional in every regard, marked by refined service, remarkable amenities, and a level of hospitality that felt both genuine and elevated. From the moment I arrived, the staff set a distinguished tone, greeting me with champagne and ensuring every detail of my visit was handled with care. The concierge team was attentive and polished, and throughout my stay I felt consistently supported by a standard of service that exceeded expectations.
Room 2791 offered a breathtaking view of the city, with floor‑to‑ceiling windows framing Chicago’s skyline in a way that felt both serene and spectacular. The terrace added an unforgettable dimension, providing a private space to enjoy the city’s energy from above while still feeling completely at ease. Room service was prompt, beautifully prepared, and consistently excellent, enhancing the comfort of the stay.
The spa and wellness facilities were equally impressive. Ashanti, Christian, and Byron delivered warm, professional service that made each visit feel personal, and my massage therapist provided a treatment that was both restorative and skillfully executed. The sauna, steam room, and gym were immaculate, calming, and thoughtfully maintained, offering a perfect balance of relaxation and rejuvenation. Pablo also stood out for his gracious and attentive service.
This stay left a lasting impression, and I will be making Trump Hotels a part of future travels.✨
Reviewed on Sep 18, 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 $126
CA $140 total
Sep 27 - Sep 28
includes taxes & fees
Quality Inn & Suites Woodstock near Lake Geneva
1785 S Eastwood Dr Woodstock IL
Fully refundable
CA $114
CA $127 total
Oct 18 - Oct 19
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 $141
CA $193 total
Sep 30 - Oct 1
includes taxes & fees
8.6/10 Excellent! (2,075 reviews)
"The hotel is very well maintained and clean and staff are friendly, helpful and responsive. There was an issue with the water in our building and the hotel was great about communicating the issue via text and solving it quickly. The pools are also lovely although we didn't get to enjoy those due ..."
Reviewed on Sep 19, 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.
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.
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.
Frequently asked questions
How much does a Woodstock vacation package cost?
Offering excellent value package deals from CA $784 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.
