Woodstock Vacation Packages

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Your Woodstock Vacation

Book a Woodstock vacation package and get ready for a thrilling adventure. Known for its artistic creativity and lively atmosphere, there's plenty to keep you on the move in this city. A trip to Woodstock is a superb opportunity to sightsee. Check out renowned attractions like Saskadena Six Ski Area, Billings Farm and Museum and Sugarbush Farm. Stop dreaming and start adventuring. Explore the multitude of options on Expedia today and finally put your Woodstock vacation plans in motion!

Top Woodstock Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was CA $1,166, price is now CA $1,048 per person
CA $1,048
per person
Oct 9 - Oct 12
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (121 reviews)
What a hidden gem! We wish we could stay longer to enjoy the ambience of the premises. And, the coffee/hot chocolate machine....to die for! And, best of all, Jody, the Innkeeper was fabulous! What a beautiful place, we LOVED it! <3

Reviewed on Aug 2, 2026

Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was CA $1,301, price is now CA $1,143 per person
CA $1,143
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
9.4/10 Exceptional! (128 reviews)
Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place

Reviewed on Jul 25, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was CA $1,377, price is now CA $1,225 per person
CA $1,225
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (876 reviews)

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,334, price is now CA $1,190 per person
CA $1,190
per person
Oct 9 - Oct 12
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (941 reviews)

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was CA $1,640, price is now CA $1,504 per person
CA $1,504
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.8/10 Excellent! (27 reviews)
Enjoyable and beautiful place. Ann

Reviewed on Jul 20, 2026

Ready to book your vacation to Woodstock?

 

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Woodstock Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $594 per night from Aug 16 to Aug 17
CA $594
CA $715 total
Aug 16 - Aug 17
includes taxes & fees
Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $346 per night from Aug 4 to Aug 5
CA $346
CA $412 total
Aug 4 - Aug 5
includes taxes & fees
On The River Inn
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
The price is CA $211 per night from Aug 5 to Aug 6
CA $211
CA $251 total
Aug 5 - Aug 6
includes taxes & fees
8.8/10 Excellent! (969 reviews)
"It would be great to have a coffee maker in the room"

Reviewed on Jul 31, 2026

The Shire Woodstock
See all 2,691 properties in Woodstock
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Stay near popular Woodstock attractions

A herd of cows grazing in a fenced pasture with trees and a building in the background.

Billings Farm and Museum

9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
See properties

Frequently asked questions

How much does a Woodstock vacation package cost?
Offering excellent value package deals from CA $1,048 on Expedia, you'll be thrilled with how little a vacation to Woodstock costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Woodstock?
You can usually find lower prices and better availability in January, April and May. Take a look at our cheap Woodstock vacation packages and you could land some great off-season discounts.
How many days is enough for Woodstock?
Typically, a few days is ideal for a Woodstock vacation. With a well-planned itinerary, you can check out all the top sights such as Billings Farm and Museum, as well as discover some hidden treasures along the way.
Is it worth booking a vacation package to Woodstock?
Popular for its nature, hiking and views, a Woodstock vacation is a hit with all kinds of visitors. Be sure to check out major sights like Billings Farm and Museum and Woodstock Town Hall Theatre, and consider renting a set of wheels for day trips to explore even more.
How to find the best Woodstock package deals?
Use Expedia's handy filters to find some fabulous Woodstock package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Woodstock package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Woodstock vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Woodstock getaway to match your exact needs. Choose 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?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Woodstock break.
How to plan a trip to Woodstock?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to travel to Woodstock.
  2. Budget wisely: Besides the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Woodstock.
  3. Decide your trip length: Think about how long you'd like to spend exploring Woodstock. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, book the ideal Woodstock vacation package for you.

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