Woodstock Vacations

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Find the Best Woodstock Vacation Packages

Woodstock Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is ₩556,026 per night from Sep 2 to Sep 3
₩556,026
₩672,944 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (532 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
The price is ₩239,314 per night from Aug 28 to Aug 29
₩239,314
₩279,034 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (807 reviews)
"Forth time at The Shire, everything was wonderful!!"

Reviewed on Aug 21, 2025

The Shire Woodstock
The Jackson

The Jackson

4 out of 5
43 Senior Lane, Woodstock, VT
The price is ₩293,760 per night from Aug 31 to Sep 1
₩293,760
₩323,136 total
Aug 31 - Sep 1
includes taxes & fees
9.8/10 Exceptional! (226 reviews)
Adorable Inn
"The Inn is adorable. Our bed was very comfortable and the shower was wonderful. I was surprised it didn’t come with breakfast since when I read the reviews before I booked it everyone raved about the breakfast. The caretaker was absolutely delightful!!"

Reviewed on Aug 22, 2025

The Jackson
See all 2,614 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.

Frequently asked questions

How much does a Woodstock vacation package cost?
Offering great value package deals 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.

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