A variety of potted flowers and pumpkins on a wooden table in an outdoor setting.

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

Prepare to experience Woodstock on your terms with a custom Woodstock vacation package! Uncovering the best parts of this interesting city is simple with a base in a neighborhood such as Killingly, which is good for nature, among other things. Every trip to Woodstock needs a well-thought-out itinerary. Fill yours with famous sights like Taylor Brooke Winery, Little River Plaza Shopping Center and Harrisville Golf Course. Don't delay visiting this destination any longer. The perfect Woodstock vacation is only a few clicks away with Expedia.

Top Woodstock vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Dec 24 - Dec 28

    Comfort Inn & Suites Plainville-Foxboro + Flight

    Plainville
    4 nights
    2.5 star property
    8.6/10 - Excellent (1,003 reviews)
    Roundtrip • Toronto (YTO) - Providence (PVD)
    YTZ - BOS • 1 stop BOS - YTZ • 1 stop
    CA $746
    CA $706
    per traveller
    found 6 hours ago
    Comfort Inn & Suites Plainville-Foxboro
  • Feb 5 - Feb 8

    The General Stanton Inn + Flight

    Charlestown
    3 nights
    3.0 star property
    9.2/10 - Wonderful (157 reviews)
    "The food in the dining room was delicious. Nice atmosphere. We would probably come back again to eat and stay the night."
    Reviewed November 9, 2026
    Roundtrip • Edmonton (YEA) - Providence (PVD)
    YEG - BDL • 2 stops BDL - YEG • 2 stops
    CA $1,226
    CA $1,131
    per traveller
    found 1 day ago
    The General Stanton Inn
  • Feb 5 - Feb 8

    La Quinta Inn & Suites by Wyndham Stonington-Mystic Area + Flight

    Pawcatuck
    3 nights
    3.0 star property
    9.0/10 - Wonderful (1,001 reviews)
    Roundtrip • Edmonton (YEA) - Providence (PVD)
    YEG - BDL • 2 stops BDL - YEG • 2 stops
    CA $1,171
    CA $1,101
    per traveller
    found 1 day ago
    La Quinta Inn & Suites by Wyndham Stonington-Mystic Area
  • Feb 5 - Feb 8

    Winnapaug Inn + Flight

    Westerly
    3 nights
    2.0 star property
    8.4/10 - Very good (1,000 reviews)
    Roundtrip • Edmonton (YEA) - Providence (PVD)
    YEG - BDL • 2 stops BDL - YEG • 2 stops
    CA $1,219
    CA $1,155
    per traveller
    found 1 day ago
    Winnapaug Inn
  • Feb 5 - Feb 8

    DELAMAR MYSTIC + Flight

    Rossie Velvet Mill Historic District
    3 nights
    4.0 star property
    9.6/10 - Exceptional (18 reviews)
    Roundtrip • Edmonton (YEA) - Providence (PVD)
    YEG - BDL • 2 stops BDL - YEG • 2 stops
    CA $1,684
    CA $1,602
    per traveller
    found 1 day ago
    DELAMAR MYSTIC

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?

You'll find cheap prices from CA $706 on Expedia for your Woodstock getaway. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Woodstock costs.

What are the cheapest months to go to Woodstock?

To pick up cheap Woodstock vacation packages, plan your trip outside of peak periods like public holidays and major festivals. You'll generally find better availability and lower prices for flights and hotels.

How many days is enough for Woodstock?

The ideal duration of your Woodstock vacation depends on what you'd like to see. Usually, a handful of days to a week will give you time to go to all the leading attractions and discover some hidden gems along the way.

Is it worth booking a vacation package to Woodstock?

Boasting a host of highlights starting with its excellent camping, Woodstock is a good vacation destination. Whether you'd like to visit attractions such as Roseland Park Golf Course and Harrisville Golf Course or take the road less travelled, you'll have plenty to see and do on your Woodstock vacation.

How to find the best Woodstock package deals?

Begin your search for a Woodstock package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Woodstock package deal straight away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Woodstock getaway off to a flying start.

Is it cheaper to book a Woodstock vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can customize your Woodstock escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.

When to book a vacation package to Woodstock?

If you've got your Woodstock travel dates finalized, book as early as you can to snap up some outstanding deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.

How to plan a trip to Woodstock?

  1. Choose when to go: Check your calendar and get your bags packed. Your favourite season and the activities available will also help you decide when to visit Woodstock.
  2. Plan your budget wisely: As well as the price of your stay, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that may crop up during your trip to Woodstock.
  3. Decide how long to go for: Now that you're more familiar with Woodstock, you can work out the ideal length of your vacation. Pull together a rough plan and allocate enough time to cover everything you want to see.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Woodstock vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.