Woodstock Vacation Packages
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Your Woodstock Vacation
Our Woodstock vacation packages let you customize your own adventure. Tailor your getaway to suit your needs and interests and make the most of your time in this fabulous city. A trip to Woodstock is an ideal opportunity to see the sights. Be sure to look around well-known attractions like Shenandoah Vineyards, Shenandoah County Fairgrounds and Woodstock Museum. Stop dreaming and start doing. Browse the wide range of options on Expedia today and put your Woodstock vacation plans in motion!
Top Woodstock Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Crowne Plaza Crystal City-Washington, D.C. by IHG
Crystal City
CA $886
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very good! (1,002 reviews)
The property was extremely clean and the staff was amazing. Elevators seemed to be jacked up for our whole stay. Great convenient location. Great water pressure and good ac which is important to us.
Reviewed on Aug 10, 2026
Ready to book your vacation to Woodstock?
Woodstock Hotel Deals
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
1130 Motel Dr Woodstock VA
Fully refundable
CA $135
CA $152 total
Sep 6 - Sep 7
includes taxes & fees
Comfort Inn Woodstock Shenandoah
1011 Motel Dr Woodstock VA
Fully refundable
CA $127
CA $143 total
Aug 23 - Aug 24
includes taxes & fees
Hampton Inn & Suites Woodstock, VA
1150 Motel Dr Woodstock VA
Fully refundableReserve now, pay when you stay
CA $147
CA $165 total
Sep 7 - Sep 8
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)
Take the family on an outing to Shenandoah County Fairgrounds during your trip to Woodstock. While you're here, you can savor the top-notch restaurants.
Woodstock Museum
8.8/10 (15 reviews)
You can spend time studying the exhibits at Woodstock Museum during your travels in Woodstock. While you're here, you can savor the top-notch restaurants.
Woodstock Recreational Area
Explore the great outdoors at Woodstock Recreational Area, a lovely green space in Woodstock. While in this family-friendly area, you can savor the top-notch restaurants.
Woodstock Tower Observation Site
8.4/10 (28 reviews)
You can find out about the history of Woodstock with a visit to Woodstock Tower Observation Site. While in this vibrant area, you can savor the top-notch restaurants.
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.
Seven Bends State Park
9.0/10 (19 reviews)
You can take time to visit Seven Bends State Park during your travels to Woodstock. While in this family-friendly area, you can savor the top-notch restaurants.
7 East Gallery
8.6/10 (7 reviews)
You can spend an afternoon browsing the exhibits at 7 East Gallery during your trip to Woodstock. While you're here, you can savor the top-notch restaurants.
W.O. Riley Park
8.6/10 (15 reviews)
Explore the great outdoors at W.O. Riley Park, a lovely green space in Woodstock. Savor the top-notch restaurants and lively bars while in town.
Frequently asked questions
How much does a Woodstock vacation package cost?
Offering excellent value package deals from CA $658 on Expedia, you'll be thrilled with how little a vacation to Woodstock costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Woodstock?
If you're looking to snag a cheap Woodstock vacation package, consider visiting in December, January and February. You'll generally find lower prices on hotels and flights during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Woodstock?
When planning your Woodstock vacation, a few days will be enough to tour all the highlights. Be sure to stop by Seven Bends State Park — it's one of the top attractions in this destination. If you're after more activities, think about basing yourself here and venturing off on some trips from Woodstock.
Is it worth booking a vacation package to Woodstock?
It's easy to see why a Woodstock vacation is on the must-do list of many travellers. Major attractions like Shenandoah County Fairgrounds are just the start of things to keep you busy here.
How to find the best Woodstock package deals?
Finding a cheap Woodstock package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Woodstock package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Woodstock vacation as a package?
You can enjoy significant savings on your next Woodstock escape by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Woodstock?
If you have your Woodstock travel dates confirmed, book as soon as you can to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Woodstock?
- Pick the ideal time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to visit Woodstock.
- Plan your budget wisely: As well as the price of your hotel, you should factor in other expenses. These include food, flights and transportation. Also, set aside a little extra for unexpected expenses that may come up during your trip to Woodstock.
- Decide how many days away: Start by listing all the sights and activities you'd like to experience in Woodstock. Then, estimate how long you'll need at each, including any travel time.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to pick a Woodstock vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
