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 ￥52,545 per night from Nov 30 to Dec 1
￥52,545
￥64,826 total
Nov 30 - Dec 1
includes taxes & fees
Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is ￥20,823 per night from Dec 6 to Dec 7
￥20,823
￥26,098 total
Dec 6 - Dec 7
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Filthy carpets and shower curtains."

Reviewed on Nov 13, 2026

On The River Inn
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 ￥19,838 per night from Dec 14 to Dec 15
￥19,838
￥23,568 total
Dec 14 - Dec 15
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Property was in a good location. Very pretty. No tissues in bathroom. Tv did not work. The whole time we were there it had “No service” it read on screen. That wouldn’t have been an issue because I also had an iPad and iphone but the WiFi was sketchy at best."

Reviewed on Nov 13, 2026

The Shire Woodstock
See all 2,745 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.

Stay near popular Woodstock attractions

A herd of cows grazing in a fenced pasture with trees and a building in the background.

Billings Farm and Museum

9.2/10 (84 reviews)
This working dairy farm showcases Vermont's rural heritage through its historic 1890 Farm Manager's House. Watch cow milking, explore interactive exhibits, and experience traditional farming practices firsthand.
See properties

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.