Woodstock Holidays

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Your Woodstock Holiday

Book a Woodstock holiday package and get ready for a thrilling adventure. Known for its artistic creativity and lively atmosphere, there's plenty to keep you on the move in this city. A trip to Woodstock is a superb opportunity to sightsee. Check out renowned attractions like Saskadena Six Ski Area, Billings Farm and Museum and Sugarbush Farm. Stop dreaming and start adventuring. Explore the multitude of options on Expedia today and finally put your Woodstock holiday plans in motion!

Woodstock Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
870
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Saskadena Six Ski Area, Montshire Museum of Science and Woodstock Town Hall Theatre

Top hotels in Woodstock

Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green Woodstock VT
£589
27 Oct - 28 Oct
includes taxes & fees
9.4/10 Exceptional! (611 reviews)
"Our 2nd floor room with balcony was beautiful, large, clean, and with excellent amenities, also looking over the waterfront. The bed was very comfortable. We enjoyed breakfast each morning very much. Our server is friendly and helpful. We were able to get close-in parking. Desk staff were also friendly. ..."

Reviewed on 27 Sept 2026

Woodstock Inn & Resort
The Jackson

The Jackson

43 Senior Lane Woodstock VT
£195
26 Oct - 27 Oct
includes taxes & fees
9.6/10 Exceptional! (323 reviews)
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."

Reviewed on 27 Sept 2026

The Jackson
The Shire Woodstock

The Shire Woodstock

46 Pleasant St. Woodstock VT
£210
29 Oct - 30 Oct
includes taxes & fees
8.8/10 Excellent! (996 reviews)
"We loved everything about this hotel. It was a short walk to get downtown. Rooms were very clean. We loved the different areas for coffee so we didn’t have to walk too far in the morning."

Reviewed on 26 Sept 2026

The Shire Woodstock
See all 2,755 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.
All Inclusive Holidays
All Inclusive Holidays
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LGBTQ+ Holidays
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Romantic Holidays
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Where to go when
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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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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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Middle Covered Bridge

You can learn about the history of Woodstock with a stop at Middle Covered Bridge. While in this quaint area, you can savour 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 travel package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Woodstock from just . And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.
If I'm not able to travel, can I cancel my Woodstock travel package?
You can cancel your Woodstock booking if your plans have been upended. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Woodstock?
Bundling your hotel and flight with Expedia won't just save precious time — it'll save you a few dollars too. A Woodstock travel package makes it simple to put together your perfect trip. With more than 550 airlines around the world to pick from, finding convenient flights that suit your busy schedule won't be hard. On top of that, we've got over 1,000,000 hotel options globally to choose from. Now that's what we call choice. No matter who you are, Expedia will help show you the world.
Does Expedia offer Book Now, Pay Later Woodstock holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply choose the payment plan best suited to your needs during the checkout process and take away the stress of budgeting for your trip. Don't forget to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:
  • Pay monthly holidays: If paying bite-sized amounts each month is something that would work for you, Klarna offers just that! Paying in easy monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking on the "book now" button is much easier with this option. Just put down a small deposit on your holiday and then start packing your suitcase.
Where should I stay in Woodstock?
With interesting attractions such as Woodstock Country Club and Suicide Six Ski Area in this area, look for a hotel located near them. Woodstock Town Hall Theatre is another sight in Woodstock that draws in the crowds.
What are the top hotels in Woodstock?
White River Inn and Suites and Hotel Coolidge are a couple of the most well-known hotels in Woodstock. Why not check out the facilities and rates at each and then make a decision?
How far in advance should I book my Woodstock holiday?
While not all air carriers advertise ticket prices early, it's usually possible to look up international airfares on Expedia up to 12 months in advance. This is the time when you'll score some incredible deals. If you've left everything to the last minute, you may still be in luck. Sometimes the lowest prices become available a few weeks before departure.
What does an Expedia Woodstock travel package include?
Expedia has everything you need to organise your Woodstock getaway, but how your package is structured is totally up to you. Select from any combination of hotels, rental cars and flights. In search of some tours or activities to fill in your time? Once you've made your booking, you can add them too. No matter your style or budget, there's a deal to meet your needs.
What should I know before booking a Woodstock travel package?
Our prices are always low. However, you'll pick up even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Woodstock Expedia travel package?
Yes — that's one of the best things about an Expedia travel package. You're in charge! We have access to more than 550 airline partners throughout the world, so you have options galore when planning your Woodstock trip.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.