Woodstock Vacations from $873

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Your Woodstock Vacation

Book a Woodstock vacation 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 vacation plans in motion!

The Latest Woodstock vacation packages

Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area
$873
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.6/10 Excellent! (878 reviews)
Pool was nice with dry and steam sonna. Restaraunt and bar was good not a big food selection but food was good quality. Lift base was very near the facility with a lot of trails nearby

Reviewed on Aug 9, 2026

The Shire Woodstock

The Shire Woodstock

Save 100% on your flight
$1,421
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (968 reviews)
Nice place to stay was major construction going on which didn't bother us too much but might have been nice to be aware beforehand. We had a lovely room on the second floor.

Reviewed on Aug 11, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

Clock Tower Base Area
$1,050
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (27 reviews)
Enjoyable and beautiful place. Ann

Reviewed on Jul 20, 2026

Solitude Village at Okemo  by Vail Resorts

Solitude Village at Okemo by Vail Resorts

Clock Tower Base Area
$962
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
7.8/10 Good! (35 reviews)
The Vesper

The Vesper

$1,354
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
9.2/10 Wonderful! (68 reviews)
It would be $100 less per night if not located in Woodstock. Railing to second floor wobbled and staircase runner not tacked down; small room with 3 tiny tables and table lights, no light in walk-in closet, no place to open luggage. Bathroom across hall with tube/shower without safety hand rail or non-skid bath mat.

Reviewed on Jul 31, 2026

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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 firsthand.
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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 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 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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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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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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Woodstock Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

Fourteen The Green Woodstock VT
$449 nightly
$494 total
Sep 7 - Sep 8
Total with taxes and fees
9.4/10 Exceptional! (598 reviews)
"Amazing! Will visit again."

Reviewed on Aug 7, 2026

Woodstock Inn & Resort
On The River Inn

On The River Inn

1653 West Woodstock Road Woodstock VT
$276 nightly
$303 total
Sep 6 - Sep 7
Total with taxes and fees
9.4/10 Exceptional! (1,008 reviews)
"Everything was good I cannot complain"

Reviewed on Aug 12, 2026

On The River Inn
The Shire Woodstock

The Shire Woodstock

46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
$268 nightly
$295 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (974 reviews)
"Nice place to stay was major construction going on which didn't bother us too much but might have been nice to be aware beforehand. We had a lovely room on the second floor."

Reviewed on Aug 11, 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.

Find the Best Woodstock Vacation Packages

Things to do in and around Woodstock

Woodstock, Vermont, is a fantastic destination for outdoor enthusiasts, offering thrilling adventures such as skiing at its renowned ski resorts and fields. Visitors can explore various activities, including guided tours and day trips that showcase the area's natural beauty. Whether you're seeking adrenaline-pumping experiences or a relaxing getaway, Woodstock provides a perfect blend of adventure and leisure for an unforgettable vacation.

Shopping

In Woodstock, you can shop at Red Wagon Toy Company for unique toys and gifts. For a short drive, visit Quechee Gorge Village, just 6 miles away. If you're up for a drive, King Arthur Baking Company, located 12 miles away, offers delightful baking supplies and treats.

Recreation

Experience the charm of the Woodstock Town Hall Theatre, where culture and entertainment blend for a delightful evening. Enjoy outdoor sports and picturesque views at the Woodstock Country Club, perfect for golf enthusiasts. For family-friendly fun, visit the Upper Valley Aquatic Center, offering a refreshing aquatic experience just 9 miles away.

Adventure

Experience thrilling skiing at Killington Resort, located 14 miles from Woodstock, or enjoy the local slopes at Saskadena Six Ski Area. For a different adventure, challenge yourself at the Green Mountain Rock Climbing Center, only 3 miles away, where outdoor sports meet excitement.

Nightlife

In Woodstock, Vermont, experience a quaint nightlife with cozy taverns and charming pubs. Visit the Woodstock Inn's bar for craft cocktails or enjoy live music at local venues. The warm, inviting atmosphere makes for a perfect evening after exploring the beautiful town's daytime attractions.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Woodstock

Woodstock, Vermont, is a perfect destination for ski enthusiasts and outdoor adventurers. Explore its rich culture and history by visiting local attractions, including national parks, historic colleges, and iconic bridges. Whether you're traveling with family or seeking a unique experience, Woodstock offers a variety of activities that cater to all interests, making it an ideal spot for your next vacation.

  • Quechee Gorge Bridge: Experience breathtaking views at Quechee Gorge Bridge, a stunning canyon located 6 miles from Woodstock. The bridge offers outdoor adventures and picturesque scenery, making it a perfect spot for hiking and photography enthusiasts.
  • Dartmouth College: Located 13 miles away, Dartmouth College is a historic campus rich in culture and tradition. Stroll through its charming grounds, admire the architecture, and soak in the vibrant academic atmosphere while exploring the college's museums and galleries.
  • Billings Farm and Museum: Situated within Woodstock, Billings Farm and Museum brings the region's agricultural history to life. Enjoy interactive exhibits, farm animals, and seasonal events that celebrate rural heritage, making it an enriching experience for visitors of all ages.

Best time to go to Woodstock

The best time to visit Woodstock is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January19.6°F (-6.9°C)Light RainMostly CloudyAverageAverage
February21.6°F (-5.8°C)Light RainMostly CloudySlightly LowSlightly High
March29.7°F (-1.3°C)Light RainMostly CloudySlightly LowAverage
April42.1°F (5.6°C)Light RainMostly CloudySlightly LowSlightly Low
May55.2°F (12.9°C)Light RainMostly SunnyAverageSlightly Low
June62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
July68.7°F (20.4°C)Light RainMostly SunnySlightly HighAverage
August66.9°F (19.4°C)Light RainMostly SunnyAverageAverage
September59.7°F (15.4°C)Light RainMostly SunnySlightly HighAverage
October48.0°F (8.9°C)Light RainMostly CloudySlightly HighSlightly High
November35.4°F (1.9°C)Light RainMostly SunnyAverageSlightly Low
December26.8°F (-2.9°C)Light RainMostly CloudyAverageSlightly High

Tips to save on your trip to Woodstock

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically April to May and November) for more affordable package holidays to Woodstock.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Woodstock Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
870
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Saskadena Six Ski Area, Montshire Museum of Science and Woodstock Town Hall Theatre

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Frequently asked questions

How much does a Woodstock vacation package cost?
Offering great value package deals from $873 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?
You can generally find lower prices and better availability in July, November and December. Explore our cheap Woodstock vacation packages and you could score some great off-season deals.
How many days is enough for Woodstock?
For your Woodstock vacation, a handful of days will be enough to tour the top spots. Be sure to visit Marsh-Billings-Rockefeller National Historical Park — it's one of the major sights in this destination. If you're after more adventure, think about basing yourself here and heading off on some day tours from Woodstock.
Is it worth booking a vacation package to Woodstock?
Woodstock has all the ingredients you need for a memorable break — nature, hiking and views are just the start. Whether you'd like to check out attractions like Marsh-Billings-Rockefeller National Historical Park and Woodstock Town Hall Theatre, or venture off the beaten track, you'll find plenty to see and 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. Choose the ideal time to travel: Your schedule, favorite season and the type of weather you enjoy can all impact your decision on when to visit Woodstock.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to airfares and activities. Your hotel will probably be the largest expense during your trip to Woodstock.
  3. Explore Woodstock with Expedia's trip planning tool: Gain insights into the top attractions and best stays for your trip to Woodstock. You can also save your favorite places, collaborate with friends and family and organize all your plans in one place.
  4. Work out your trip length: Consider how long you want to spend exploring Woodstock. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Woodstock vacation package that brings all your bookings together.
  6. Book experiences or activities ahead of time: Whether it's a ticket to a major attraction or a day trip, you won't have to worry about missing out on the best Woodstock has to offer. Find all the fun things to do in Woodstock with our dedicated activity guide.
Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Your Woodstock trip should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you a little more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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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.