Woodstock Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Woodstock
Price found within the past 48 hours. Click for updated prices.
Top hotels in Woodstock
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
1130 Motel Dr Woodstock VA
Fully refundable
€108
31 Aug - 1 Sept
includes taxes & fees
Comfort Inn Woodstock Shenandoah
1011 Motel Dr Woodstock VA
Fully refundable
€91
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Clean room. Staff at front desk helpful and friendly. Close to several different food choices. Breakfast was standard fare for hotels in this chain."
Reviewed on 27 Aug 2026
Hampton Inn & Suites Woodstock, VA
1150 Motel Dr Woodstock VA
Fully refundableReserve now, pay when you stay
€94
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"."
Reviewed on 25 Aug 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
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 artefacts and antique toys that tell Shenandoah County's storey. 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 splendour.
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 savour the top-notch restaurants.
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.
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.
Frequently asked questions
How much does a Woodstock holiday package cost?
You can snap up a holiday package to this top destination from €1,003 on Expedia. But how much your holiday 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 holiday packages. Travelling in less busy months means you can generally find lower prices on flights and accommodation.
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 holiday, check out which kind of activities and day tours are available nearby.
Is it worth booking a holiday package to Woodstock?
Woodstock has everything you need for an unforgettable getaway. Begin your Woodstock holiday 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 personalise 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Woodstock holiday as a package?
An Expedia holiday 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 holiday 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 favourite 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 holiday. Put together a rough plan and allocate enough time for all the things you want to do.
- Combine your airfare and accommodation: Once you've settled on your trip dates and duration, book the perfect Woodstock holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
