Woodstock Vacations

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Find the Best Woodstock Vacation Packages

Woodstock Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green Woodstock VT
SAR 1,385
SAR 1,688 total
16 Nov - 17 Nov
includes taxes & fees
Woodstock Inn & Resort
The Jackson

The Jackson

43 Senior Lane Woodstock VT
SAR 462
SAR 509 total
16 Nov - 17 Nov
includes taxes & fees
The Jackson
On The River Inn

On The River Inn

1653 West Woodstock Road Woodstock VT
SAR 612
SAR 749 total
8 Nov - 9 Nov
includes taxes & fees
On The River Inn
See all 2,762 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.
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A calm lake surrounded by dense green forest and a clear sky.
Photo by Jessie Festa

Marsh-Billings-Rockefeller National Historical Park

9.4/10 (40 reviews)
Explore America's only national park dedicated to conservation history through its Victorian mansion and historic forest. Wander scenic carriage roads while discovering three generations of environmental stewardship.
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A snow-covered mountain landscape with ski trails and trees.

Saskadena Six Ski Area

8.8/10 (35 reviews)
This historic ski area established in 1935 offers 23 trails across 100 acres of Vermont terrain. Enjoy a charming, low-key atmosphere with runs suitable for all skill levels and a cozy lodge experience.
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A lake with white birds and tall grasses.

Lakota Lake

8.0/10 (1 review)
This serene 15-acre reservoir sits amid private Vermont forest, dating back to 1891. Morning visits reward with calm waters and active wildlife, though advance arrangements through the Lakota Club are required.
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Woodstock Town Hall Theatre

9.4/10 (13 reviews)
This historic neoclassical theater captivates with its outstanding natural acoustics and intimate 386-seat design. Enjoy live performances or first-run films while savoring the locally beloved maple butter popcorn.
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Middle Covered Bridge

You can learn about the history of Woodstock when you stop by Middle Covered Bridge. While in this quaint area, you can savor the top-notch restaurants.
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Red Wagon Toy Company

4.0/10 (2 reviews)
This whimsical Vermont toy shop offers a curated selection of unique playthings and the famous Rody bouncing toys. Browse quality educational items for infants to big kids in this charming Woodstock gem.
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Taftsville Covered Bridge

9.6/10 (45 reviews)
Vermont's historic Taftsville Covered Bridge has spanned the Ottauquechee River since 1836. Capture its rustic timber-framed charm against vibrant autumn foliage for a quintessential New England photograph.
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Frequently asked questions

How much does a Woodstock vacation package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little 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?
You can usually find lower prices and better availability in January, April and May. Take a look at our cheap Woodstock vacation packages and you could land some great off-season discounts.
How to find the best Woodstock package deals?
Use Expedia's handy filters to find some fabulous Woodstock package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Woodstock package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Woodstock vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking stays and flights separately. Better still, you can tailor your Woodstock getaway to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Woodstock?
Secure fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Woodstock break.
How to plan a trip to Woodstock?
  1. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to travel to Woodstock.
  2. Budget wisely: Besides the price of your stay, you should consider other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Woodstock.
  3. Decide your trip length: Think about how long you'd like to spend exploring Woodstock. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, book the ideal Woodstock vacation package for you.