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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
May 17 - May 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
9/10 Wonderful! (439 reviews)
Easy check on thru text. No staff after 4PM. Cozy place and room was nice. Close to Mount Snow ski area.

Reviewed on Mar. 30, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Jun. 13 - Jun. 16
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.8/10 Excellent! (733 reviews)
Great hotel, room was cute and with a nice view. 5 min walk to downtown. If we needed anything we just texted the front desk and they got us what we needed. Would stay again!

Reviewed on Feb. 21, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Jun. 13 - Jun. 16
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (717 reviews)
The staff is very helpful knowledgeable and respectful.

Reviewed on Apr. 2, 2025

Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
per person
Jun. 13 - Jun. 16
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8/10 Very Good! (25 reviews)
Very friendly costumer service, we arrived late and we're greated with kindness.

Reviewed on Sep. 16, 2024

The Hartness House

The Hartness House

3 out of 5
per person
Jun. 13 - Jun. 16
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
8.2/10 Very Good! (308 reviews)
Nice place, but no staff. Wasn’t an issue but weird. The mansion is really pretty.

Reviewed on Mar. 15, 2025

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 $427 per night from Apr. 6 to Apr. 7
CA $427
CA $533 total
includes taxes & fees
Apr 6 - Apr 7
9.2/10 Wonderful! (507 reviews)
Wonderful friendly staff and great environment
"All the staff, whether the bartender, wait staff, men at the front door, desk clerk everyone greeting my wife and I with a smile and were very helpful."

Reviewed on Mar. 29, 2025

Woodstock Inn & Resort
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Apr. 7 to Apr. 8
CA $179
CA $209 total
includes taxes & fees
Apr 7 - Apr 8
8.6/10 Excellent! (732 reviews)
Great Spot !
"Clean, nice, great value, nice place"

Reviewed on Mar. 22, 2025

The Shire Woodstock
Sleep Woodstock Motel
Sleep Woodstock Motel
2 out of 5
4324 West Woodstock Road, Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Apr. 14 to Apr. 15
CA $145
CA $184 total
includes taxes & fees
Apr 14 - Apr 15
9.6/10 Exceptional! (476 reviews)
"Thank"

Reviewed on Mar. 31, 2025

Sleep Woodstock Motel
See all 2,653 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

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Frequently asked questions

How much does a Woodstock vacation package cost?
Offering great value package deals from CA $866 on Expedia, you’ll be pleasantly surprised at how much 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?
January, April and May are great times to look for cheap Woodstock vacation packages. Choosing to travel in less busy periods means you can usually find lower prices on flights and accommodations.
How many days is enough for Woodstock?
For your Woodstock vacation, a few days will be enough to tour the top spots. Be sure to visit Mount Tom Peak — it’s one of the top 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?
Woodstock has everything you need for an awesome break — nature, hiking and views are just the start. Whether you want to check out attractions like Billings Farm and Museum and Woodstock Town Hall Theatre, or take the road less traveled, you’ll have plenty to do on your Woodstock vacation.
How to find the best Woodstock package deals?
Begin your search for a Woodstock package deal by entering your destination and travel dates under our “Packages” tab. Then apply some filters, like “Popular locations” and “Property type,” to tailor the results to your exact needs. You can also sort by “Package discount” and discover offers that come with big savings. If you don’t find the perfect Woodstock package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Woodstock escape off to a flying start.
Is it cheaper to book a Woodstock vacation as a package?
You can enjoy significant savings on your Woodstock retreat by booking a personalized vacation package. Check the “Package” heading, then select your travel dates and destination to see the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Woodstock?
Score amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Woodstock escape.
How to plan a trip to Woodstock?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Woodstock.
  2. Plan your budget wisely: As well as the price of your hotel, you’ll need to factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Woodstock.
  3. Decide how long to go for: Now that you’re up to speed on Woodstock, you can figure out the perfect length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your accommodations and airfare: After you’ve nailed down your trip dates and duration, lock in the right Woodstock vacation package for you.

Discover the most popular places to visit in Woodstock

Billings Farm and Museum

Billings Farm and Museum

5/5(1 review)

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.

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