Woodstock Vacations from ￥364,082
Book a Hotel + Flight or Car together to unlock savings
The Latest Woodstock Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
￥364,082
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip flight included
Takamatsu (TAK) to Springfield (VSF)
10/10 Exceptional! (129 reviews)
Beautiful property set in a fantastic town. Proprietors were super nice and the property was absolutely beautiful. Would 100% recommend staying here.
Reviewed on Oct 24, 2026
Find the Best Woodstock Vacation Packages
Woodstock Hotel Deals
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
￥57,885
￥70,576 total
Nov 16 - Nov 17
includes taxes & fees
9.4/10 Exceptional! (624 reviews)
"Amazing venue for our wedding!"
Reviewed on Oct 25, 2026
On The River Inn
1653 West Woodstock Road Woodstock VT
￥25,598
￥31,295 total
Nov 15 - Nov 16
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"Great place would stay again"
Reviewed on Oct 25, 2026
The Shire Woodstock
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
￥18,085
￥21,485 total
Nov 9 - Nov 10
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Friendly staff, large room with beautiful property & riverview."
Reviewed on Oct 25, 2026
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
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.
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.
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.
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.
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.
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.
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.
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.
Frequently asked questions
How much does a Woodstock vacation package cost?
Offering great value package deals from ￥364,082 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?
January, April and May are great times to look for cheap Woodstock vacation packages. Choosing to travel in less busy periods means you can usually find lower prices on flights and accommodations.
How many days is enough for Woodstock?
For your Woodstock vacation, 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 vacation 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 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?
- 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.
- 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.
- 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.
- Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the right Woodstock vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
