Woodstock Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Woodstock Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Greenwood Inn & Suites

Greenwood Inn & Suites

CA $841
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Deer Lake (YDF)
8/10 Very good! (1,623 reviews)
Appalachian Chalets & RV

Appalachian Chalets & RV

CA $937
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
St. John's (YYT) to Deer Lake (YDF)
9.4/10 Exceptional! (121 reviews)
The cottage accommodations were immaculate. The beds and furniture were comfortable with an adequate supply of kitchen utensils. We would stay again if we were travelling in the area and recommend the cottages to fellow travellers.

Reviewed on Sep 20, 2026

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Woodstock Hotel Deals

Blanches Hideaway

Blanches Hideaway

7b Thistle Ln Burlington NL
CA $229
CA $269 total
Sep 29 - Sep 30
includes taxes & fees
Blanches Hideaway
Charming boat house by the Ocean in beautiful Smith's Harbour, NL with WiFi

Charming boat house by the Ocean in beautiful Smith's Harbour, NL with WiFi

Smith's Harbour NL
CA $175
CA $233 total
Oct 1 - Oct 2
includes taxes & fees
10/10 Exceptional! (1 review)
"Lovely stay in this picturesque ‘cabin’ on the bay. We were the first couple of the season to visit and although Hughie and Diane were not there, Deanna their daughter was a delightful alternative. A few, first of the year little glitches but smoothed out easily and we loved our views and location. ..."

Reviewed on Jun 7, 2026

Charming boat house by the Ocean in beautiful Smith's Harbour, NL with WiFi
See all 4 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
Beach Vacations
Family Vacations
Family Vacations
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a Woodstock vacation package cost?
Offering great value package deals from CA $841 on Expedia, you'll be surprised at how little a vacation to Woodstock costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Woodstock?
January, February and November are great times to search for cheap Woodstock vacation packages. Opting to travel in less busy periods means you can generally find lower prices on accommodations and flights.
How many days is enough for Woodstock?
The ideal duration for your Woodstock vacation depends on what you'd like to see and do. Usually, a few days to a week will give you time to tick off all the major sights and explore some hidden gems along the way.
How to find the best Woodstock package deals?
Use Expedia's filter tool to help you find some tempting Woodstock package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Woodstock package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Woodstock vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still have the freedom to create a personalized Woodstock vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Woodstock?
Land fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Woodstock vacation.
How to plan a trip to Woodstock?
  1. Choose when to get away: Check your calendar and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to vacation in Woodstock.
  2. Plan your budget wisely: On top of the price of your hotel, you'll need to consider other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may crop up during your trip to Woodstock.
  3. Work out your trip length: Consider how long you'd like to spend discovering Woodstock. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Woodstock vacation package.

Explore a world of travel with Expedia

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