A park with a bench, trees with autumn leaves, a grassy area, and a building in the background.

Woodstock Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
  • Jan 21 - Jan 24

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything."
    Reviewed November 3, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $914
    CA $671
    per traveller
    found 0 hours ago
    Le Méridien Essex Chicago
  • Jan 21 - Jan 24

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,009 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    Save 100% on your flight
    CA $1,899
    CA $1,337
    per traveller
    found 0 hours ago
    The Peninsula Chicago
  • Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,885 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,395
    CA $992
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 21 - Jan 24

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,003 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,801
    CA $1,316
    per traveller
    found 22 hours ago
    Park Hyatt Chicago
  • Jan 21 - Jan 24

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,164 reviews)
    "The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,344
    CA $984
    per traveller
    found 22 hours ago
    Pendry Chicago

Discover the most popular places to visit in Woodstock

Woodstock Hotel Deals

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.

Frequently Asked Questions

How much does a Woodstock vacation package cost?

Offering excellent value package deals from CA $671 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.