Woodstock Vacations
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Find the Best Woodstock Vacation Packages
Woodstock Hotel Deals
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
1130 Motel Dr Woodstock VA
Fully refundable
NT$3,373
NT$3,788 total
Oct 4 - Oct 5
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Very clean, bed was comfortable, breakfast was good, overall a pleasant stay."
Reviewed on 2026/9/14
Comfort Inn Woodstock Shenandoah
1011 Motel Dr Woodstock VA
Fully refundable
NT$3,221
NT$3,617 total
Sep 30 - Oct 1
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Great stay."
Reviewed on 2026/9/17
Hampton Inn & Suites Woodstock, VA
1150 Motel Dr Woodstock VA
Fully refundableReserve now, pay when you stay
NT$3,366
NT$3,780 total
Sep 27 - Sep 28
includes taxes & fees
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
Shenandoah County Fairgrounds
9.0/10 (48 reviews)
The Shenandoah County Fairgrounds hosts the valley's oldest fair, drawing thousands with agricultural exhibits and harness races. Experience local traditions, entertainment, and regional cuisine during late August.
Woodstock Museum
8.8/10 (15 reviews)
Step into two 18th-century buildings showcasing Civil War artifacts and antique toys that tell Shenandoah County's story. Engage with knowledgeable volunteer docents who bring local heritage to life.
Woodstock Tower Observation Site
8.4/10 (28 reviews)
Built in 1935 by the Civilian Conservation Corps, Woodstock Tower offers panoramic views of the Seven Bends of the Shenandoah River. Climb to the top for breathtaking vistas of the valley and Blue Ridge Mountains.
Seven Bends State Park
9.0/10 (19 reviews)
Meander along seven distinct curves of the Shenandoah River in this tranquil riverside park. Paddle through gentle waters or hike scenic trails that showcase Virginia's natural splendor.
Shenandoah County Courthouse
Find out about the history of Woodstock when you take a trip to Shenandoah County Courthouse. While in this family-friendly area, you can savor the top-notch restaurants.
W.O. Riley Park
8.6/10 (15 reviews)
This community hub features an accessible playground, swimming pool, and sports courts in a scenic setting. Enjoy a peaceful picnic or attend one of the many seasonal events held at the covered stage.
7 East Gallery
8.6/10 (7 reviews)
This intimate cooperative gallery showcases diverse works by local Shenandoah Valley artists. Chat with the member artists on staff while browsing original paintings, photography, and handcrafted treasures.
Woodstock Recreational Area
W.O. Riley Park offers a vibrant community hub with swimming, sports courts, and a modern playground. Relax by the pool or catch a summer concert at the covered stage during your visit to Woodstock.
Frequently asked questions
How much does a Woodstock vacation package cost?
You can snap up a vacation package to this top destination on Expedia. But how much your vacation to Woodstock costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Woodstock?
December, January and February are the best times to search for cheap Woodstock vacation packages. Traveling in less busy months means you can generally find lower prices on flights and accommodations.
How many days is enough for Woodstock?
You can explore all the leading sights in Woodstock in a few days, including the popular Shenandoah County Fairgrounds. If you want a longer Woodstock vacation, check out which kind of activities and day tours are available nearby.
Is it worth booking a vacation package to Woodstock?
Woodstock has everything you need for an unforgettable getaway. Begin your Woodstock vacation on a high note by exploring top attractions like Shenandoah County Fairgrounds.
How to find the best Woodstock package deals?
Finding a cheap Woodstock package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply some filters and see what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Woodstock package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Woodstock vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and stays separately. Better still, you can tailor your Woodstock escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Woodstock?
Enjoy amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Woodstock trip.
How to plan a trip to Woodstock?
- Choose when to travel: Check your calendar and get packing. Your favorite time of year and the type of activities on offer will also help you decide when to visit Woodstock.
- Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will probably be the biggest expense during your trip to Woodstock.
- Decide how long to go for: Now that you know more about Woodstock, you can figure out the right length of your vacation. Put together a rough plan and allocate enough time for all the things you want to do.
- Combine your airfare and accommodations: Once you've settled on your trip dates and duration, book the perfect 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.
