Woodstock Vacation Packages

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Top Woodstock Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
per person
Feb. 21 - Feb. 24
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.8/10 Exceptional! (80 reviews)
LOVED this place! The owner was warm and welcoming AND made a great breakfast. We loved visiting with others. One couple was from California, other from England, we are from Texas. The room was spacious, clean and we felt very safe there. Next time we are in the area, we will definitely stay here again. 10/10!!! Highly recommend!

Reviewed on Oct. 23, 2024

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Feb. 9 - Feb. 15
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (696 reviews)
Nice property about a block and a half from down town Woodstock. We stayed in a smaller building next door to the main hotel. The room was very large and quiet with a king bed. I would recommend staying at The Shire. Very convenient location.

Reviewed on Dec. 21, 2024

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
per person
Feb. 9 - Feb. 15
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.2/10 Wonderful! (489 reviews)
I stay at the Woodstock Inn every December and always enjoy the stay. No detail is overlooked by the staff. I could sit in the lobby for days looking at the fire and Christmas decorations in between chapters of a stack of books.

Reviewed on Dec. 11, 2024

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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 $444 per night from Jan. 20 to Jan. 21
CA $444
CA $551 total
includes taxes & fees
Jan 20 - Jan 21, 2025
9.2/10 Wonderful! (491 reviews)
Nice time
"The room was very small yet comfortable. Bathroom was very tight. Very little space to put things. The bed was very soft and cozy. However there was a dead bug squished in The curtains. Cookies and hot chocolate were a nice touch and a wine tasing with great cheese was a special treat. The entrance ..."

Reviewed on Dec. 23, 2024

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 $191 per night from Jan. 7 to Jan. 8
CA $191
CA $234 total
includes taxes & fees
Jan 7 - Jan 8, 2025
8.6/10 Excellent! (697 reviews)
Good location
"Great view and convenient to the area"

Reviewed on Dec. 23, 2024

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 $188 per night from Jan. 2 to Jan. 3
CA $188
CA $206 total
includes taxes & fees
Jan 2 - Jan 3, 2025
9.6/10 Exceptional! (432 reviews)
"Lovely little motel not far from Woodstock and easy drive to Killington. Very clean, cozy and comfortable. Plus, Ramunto’s down the road is always a treat."

Reviewed on Dec. 25, 2024

Sleep Woodstock Motel
See all 2,537 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.

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Frequently asked questions

How much does a Woodstock vacation package cost?
Offering great value package deals from CA $964 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.