Woodstock Holidays

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Top hotels in Woodstock

Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green Woodstock VT
S$634
7 Sept - 8 Sept
includes taxes & fees
Woodstock Inn & Resort
On The River Inn

On The River Inn

1653 West Woodstock Road Woodstock VT
S$363
27 Aug - 28 Aug
includes taxes & fees
On The River Inn
The Shire Woodstock

The Shire Woodstock

46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
S$320
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (971 reviews)
"Giid hotel with several fire pits to sit by the river"

Reviewed on 6 Aug, 2026

The Shire Woodstock
See all 2,681 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 first-hand.
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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 cosy lodge experience.
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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 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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A wooden covered bridge with a sign reading "Woodstock Middle Bridge."

Ottaquechee River

9.4/10 (67 reviews)
Flowing through Vermont's countryside, the Ottauquechee River carves the dramatic Quechee Gorge, Vermont's deepest ravine. Stroll the riverside trail for serene views, especially during autumn.
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Woodstock Town Hall Theatre

9.4/10 (13 reviews)
This historic neoclassical theatre captivates with its outstanding natural acoustics and intimate 386-seat design. Enjoy live performances or first-run films while savouring the locally beloved maple butter popcorn.
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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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Mount Tom Peak

9.6/10 (32 reviews)
This forested peak offers rewarding trails leading to spectacular views of Woodstock's charming village below. Hikers will discover a perfect blend of Vermont's natural beauty and rich cultural heritage.
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Frequently asked questions

How much does a Woodstock holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday packages. Choosing to travel in less busy periods means you can usually find lower prices on flights and accommodation.
How many days is enough for Woodstock?
For your Woodstock holiday, 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 holiday 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 holiday.
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 holiday as a package?
You can enjoy significant savings on your Woodstock retreat by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday 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 accommodation and airfare: After you've nailed down your trip dates and duration, lock in the right Woodstock holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.