Woodstock, VT

Travel Guide

A red convertible car parked in front of a brick house with black shutters and a white picket fence.
A street with various shops, including 'The Prince & The Pauper' and 'Philox'.
A river with rocks, surrounded by trees with orange leaves, a grassy area, and a building in the background.
A wooden covered bridge with signs reading "Woodstock Middle Bridge 1969" and "Slippery When Wet."
A historic brick building with a sign reading "Woodstock Pharmacy" and various storefronts below.

In the seat of Windsor County, discover Vermont’s only national park, three covered bridges and dozens of shops and restaurants.

Travel back to a bygone time in Woodstock, Vermont. The picturesque town, located in the midst of the Green Mountains, remains remarkably similar in appearance to how it looked a century ago. Vermont is known for its stunning nature and charming villages in Woodstock, experience both in one place.

Discover the shopping, dining and lodging attractions of downtown Woodstock. From antiques to artwork, find something to please any shopper. Explore the beautifully preserved 19th-century brick buildings that line the streets.

Covered bridges were once common throughout New England, but now few survive. Woodstock is home to not one, but three spanning the Ottauquechee River. Try to find them all. Lincoln Bridge, a plain wooden structure, is the simplest of the three. Recognize Taftsville Bridge by its distinctive red paint. Get your camera ready at Middle Bridge, known for its intricate diamond windows.

Explore the Marsh-Billings-Rockefeller National Historical Park, dedicated to three individuals who had tremendous influence in fostering conservation and stewardship of America’s landscapes. Trek to the Pogue, a beautiful mountain pond, and learn about the area’s history and future on a guided ranger tour. Visit the stately brick George Perkins Marsh Boyhood Home. Check out the paintings and photographs inside and relax in its manicured gardens.

Discover Vermont’s rural heritage at Billings Farm and Museum. Explore the 1,000-acre (400-hectare) working dairy farm. Watch the afternoon milking and meet cows, sheep, horses, oxen and more through interactive programs. Check out historic exhibits in the 1890 Farm House and learn about life on a 19th-century farm.

Drive 10 minutes north from the town center to Suicide Six. Go skiing or snowboarding down its snowy slopes in winter months. Have fun at your own pace on trails ranging from beginner to black diamond.

To experience Vermont’s scenery and small-town charm in one place, visit Woodstock. With the Green Mountains at its doorstep, go from browsing galleries in town to traversing wilderness trails in the forest in just a few minutes.

Where to stay in Woodstock

Find the best Woodstock areas and neighborhoods for the activities you enjoy most. Learn more about Woodstock
Learn more about Woodstock

West Woodstock

Visitors highly recommend West Woodstock for its abundant dining options, and you can make a stop by Union Arena Community Center while you're in town.

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (628 reviews)
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."

Reviewed on Oct 28, 2026

Woodstock Inn & Resort
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$181 nightly
The price is $200 total per night from Nov 29 to Nov 30
$200 total
Nov 29 - Nov 30
Total with taxes and fees
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (1,005 reviews)
"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"

Reviewed on Nov 5, 2026

On The River Inn
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
$143 nightly
The price is $157 total per night from Nov 22 to Nov 23
$157 total
Nov 22 - Nov 23
Total with taxes and fees
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Shire 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.
Scenic Ridge Cabin with Sweeping Vermont Views

Scenic Ridge Cabin with Sweeping Vermont Views

Woodstock VT
Stay at this vacation home in Woodstock. Enjoy a garden, laundry facilities, and balconies. Popular attractions Saskadena Six Ski Area and Marsh-Billings-Rockefeller ...
9.4/10 Exceptional! (13 reviews)
"Great stay"

Reviewed on Oct 26, 2026

Scenic Ridge Cabin with Sweeping Vermont Views
Woodstock Village Carriage House

Woodstock Village Carriage House

Woodstock VT
Stay at this cottage in Woodstock. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Quechee Gorge Bridge and Dana House Museum are located ...
9.8/10 Exceptional! (121 reviews)
"Very clean, comfortable, and spacious."

Reviewed on Nov 6, 2026

Woodstock Village Carriage House
Woodstock Hillside Hideaway | Green Mountain Views

Woodstock Hillside Hideaway | Green Mountain Views

Woodstock VT
Stay at this cabin in Woodstock. Enjoy a garden, balconies, and an in-room coffeemaker. Popular attractions Easy Grade to TFW link and Skinny Dip are located ...
10/10 Exceptional! (3 reviews)
"The property is in a beautiful setting only a few miles from Woodstock. It was clean, comfy and as shown in the pictures. The hot tub was wonderful!"

Reviewed on Oct 17, 2026

Woodstock Hillside Hideaway | Green Mountain Views
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

Frequently asked questions

Is Woodstock worth visiting?
Woodstock is worth visiting for its local dining, offering North American and Italian cuisine. Travelers can also explore standout attractions like Billings Farm and Museum and enjoy performances at the Woodstock Town Hall Theatre, providing a mix of cultural and historical experiences.
When is the best time to visit Woodstock?
The best time to visit Woodstock is from May through September, when the weather is typically pleasant for exploring. For fewer crowds and better value, the quieter months of November through February offer a different experience with cooler temperatures, making it ideal for travelers who enjoy winter activities.
What is Woodstock known for?
Woodstock is known for institutions like the Billings Farm and Museum and the Woodstock Town Hall Theatre, plus the Saskadena Six Ski Area. This riverside city on the Ottauquechee River also offers travelers a North American food culture.
What is a good itinerary length for Woodstock?
A good itinerary length for Woodstock is two to three days to experience highlights like Billings Farm and Museum, Woodstock Town Hall Theatre, and Saskadena Six Ski Area. An extended stay of four to five days allows travelers to enjoy a more relaxed pace and explore further with activities such as the Antiques and Artisans: A Woodstock to Windsor Self-Guided Drive. See Woodstock Activities.
What are the top things to do in and around Woodstock?
Woodstock offers a mix of outdoor activities, historical sites, and cultural experiences for travelers to enjoy:


How do I plan a trip to Woodstock?
To plan your trip to Woodstock, search for places to stay and book flights and rental cars in advance. Explore activities like visiting Billings Farm and Museum or the Woodstock Town Hall Theatre. Consider the Antiques and Artisans self-guided drive, and always have indoor backups for outdoor plans, such as the Saskadena Six Ski Area.
What cuisines can you find in Woodstock?
In Woodstock, travelers can find New American cuisine, with options like gourmet burgers and artisanal pizzas. There are also Italian favorites, Southern soul food, and diverse Latin American choices including Mexican and Caribbean dishes. Additionally, you can find various Asian options like Chinese, Japanese, Thai, and Indian dishes, alongside Mediterranean cuisine.
Can I book a refundable hotel in Woodstock?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Woodstock by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Woodstock with Expedia?
Expedia makes it easier to plan your Woodstock trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Woodstock?
The best choice depends on your travel style. Hotels in Woodstock can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Woodstock trip on Expedia?
Once you've booked your Woodstock trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Woodstock trip?
Expedia offers customer support before, during, and after your Woodstock trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Woodstock?
If it's your first trip to Woodstock, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Woodstock hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Woodstock hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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