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.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
May 12 - May 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (177 reviews)
Outdoor pool was great !

Reviewed on Mar. 2, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
May 12 - May 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (718 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
May 12 - May 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (712 reviews)
Perfect proberty for walk out sking. Indoor garage that goes up ro the room.

Reviewed on Mar. 3, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
per person
May 12 - May 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.2/10 Wonderful! (500 reviews)
Great resort, beautiful property-only issue was room was cold - aside from that, loved the stay

Reviewed on Feb. 5, 2025

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
May 12 - May 15
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
No reviews
Property is new - really well renovated and comfortable. Owner Romeo is a hospitable and warm individual who goes the extra mile to make sure we were comfortable and had a great experience. Rooms were very nice, new, and beds are super comfortable. Really great boutique feel for an upscale ski weekend experience. Highly recommend this property.

Reviewed on Mar. 1, 2025

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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 $432 per night from Mar. 16 to Mar. 17
CA $432
CA $539 total
includes taxes & fees
Mar 16 - Mar 17
9.2/10 Wonderful! (502 reviews)
Perfect Spot
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. ..."

Reviewed on Feb. 22, 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 $241 per night from Mar. 5 to Mar. 6
CA $241
CA $281 total
includes taxes & fees
Mar 5 - Mar 6
8.6/10 Excellent! (727 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

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 $148 per night from Mar. 4 to Mar. 5
CA $148
CA $162 total
includes taxes & fees
Mar 4 - Mar 5
9.6/10 Exceptional! (470 reviews)
"This place was adorable, and it was a very lucky find on the eve of a storm on a holiday weekend with 2 dogs in tow. Seems to be an old motel renovated. Cute decor. There were lots of cute helpful extras packed into a small space. Coffee, tea and Cider for the Keurig, retro mini fridge, garbage can ..."

Reviewed on Feb. 27, 2025

Sleep Woodstock Motel
See all 2,592 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 $690 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.