Woodstock Vacations from $357

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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!

The Latest Woodstock vacation packages

Price found within the past 48 hours. Click for updated prices.
Phoenix Park Hotel
Residence Inn by Marriott Washington, DC National Mall
Sheraton Baltimore North Hotel
The Bethesdan Hotel, Tapestry Collection by Hilton
Hotel Burg
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Stay near popular Woodstock attractions

Woodstock Hotel Deals

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

2.5 out of 5
1130 Motel Dr Woodstock VA
Fully refundable
$112 nightly
The price is $126 total per night from Jul 26 to Jul 27
$126 total
Jul 26 - Jul 27
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
"Overall, everything was fine. I felt the bathroom seemed a bit dated. Also, was extremely disappointed in the breakfast. Everything was "mechanical", which was very unappetizing. We did try the coffee and it was terrible. We went to a Dunkin. No personal touch at all."

Reviewed on Jun 27, 2026

Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

2.5 out of 5
1011 Motel Dr Woodstock VA
Fully refundable
$100 nightly
The price is $112 total per night from Jul 19 to Jul 20
$112 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Met our needs."

Reviewed on Jun 21, 2026

Comfort Inn Woodstock Shenandoah
Hampton Inn & Suites Woodstock, VA

Hampton Inn & Suites Woodstock, VA

2.5 out of 5
1150 Motel Dr Woodstock VA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $122 total per night from Jul 19 to Jul 20
$122 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
"Excellent experience"

Reviewed on Jun 26, 2026

Hampton Inn & Suites Woodstock, VA
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.

Find the Best Woodstock Vacation Packages

Things to do in and around Woodstock

Woodstock, Virginia, is perfect for outdoor adventures and scenic getaways. Visitors can enjoy a variety of activities, including exploring recreational areas and skiing at local ski fields. Key attractions include the Woodstock Film Festival, wedding packages for couples, and various sporting events throughout the year, making it an exciting destination for both relaxation and entertainment.

Shopping

In Woodstock, you can explore the Natural Art Garden Center, just 6 miles away, for unique gifts. If you're up for a drive, visit the Shenandoah Valley Flea Market, 16 miles away, for a vibrant market experience, or check out Mt Jackson Thrift & Gift, located 12 miles from town.

Recreation

At Elkwallow Picnic Area, enjoy serene nature walks and picnic spots that promote relaxation. The Caverns Country Club offers a fun golfing experience surrounded by beautiful landscapes. Meanwhile, the Little Fort Recreation Area invites you to unwind with scenic trails and tranquil settings perfect for rejuvenation.

Adventure

Experience the Massanutten Storybook Trail, an 11-mile hike offering stunning scenery and outdoor adventure. Head to Yogi Bear's Jellystone Park, located 16 miles away, for family-friendly camping fun. For winter sports enthusiasts, Bryce Ski Resort, 15 miles from Woodstock, provides thrilling skiing and snowboarding opportunities.

Nightlife

Woodstock's nightlife features cozy pubs and vibrant local spots. Enjoy a drink at the Woodstock Brewhouse, known for its craft beers. For live music and a relaxed vibe, check out the local taverns where you can unwind with friends and catch talented musicians in action.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Woodstock

Woodstock, Virginia, is perfect for outdoor and adventure enthusiasts, offering stunning scenery and various attractions such as caves, state parks, and fairgrounds. Visitors can enjoy cultural experiences and family-friendly activities. Don't miss the Woodstock Country Club for a round of golf or explore Woodstock Farm for a taste of local agriculture. Whether you seek adventure or relaxation, Woodstock has something for everyone to enjoy.

  • Shenandoah County Fairgrounds: Experience the vibrant atmosphere of the Shenandoah County Fairgrounds, where family-friendly events and outdoor activities abound. Enjoy the lively fairs, local vendors, and community gatherings that bring a unique charm to Woodstock.
  • Woodstock Museum: Immerse yourself in the rich history and culture of Woodstock at the Woodstock Museum. Discover fascinating exhibits showcasing local heritage, art, and artifacts that reflect the town's unique story and community spirit.
  • Woodstock Tower Observation Site: For breathtaking views and a touch of adventure, head to the Woodstock Tower Observation Site. This romantic lookout offers stunning panoramas of the surrounding landscape, perfect for nature lovers and photographers alike.

Best time to go to Woodstock

The best time to visit Woodstock can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Woodstock falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Woodstock falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.3°F (-0.4°C)Light RainMostly SunnySlightly LowSlightly Low
February34.7°F (1.5°C)Light RainMostly SunnyAverageSlightly Low
March42.3°F (5.7°C)Light RainMostly SunnyAverageSlightly Low
April52.7°F (11.5°C)Light RainMostly SunnyAverageAverage
May62.1°F (16.7°C)Light RainMostly SunnyAverageSlightly High
June70.2°F (21.2°C)Light RainMostly SunnySlightly HighSlightly High
July75.0°F (23.9°C)Light RainMostly SunnySlightly HighAverage
August72.7°F (22.6°C)Light RainMostly SunnySlightly HighAverage
September66.0°F (18.9°C)Light RainMostly SunnyAverageAverage
October55.0°F (12.8°C)Light RainMostly SunnyAverageSlightly High
November43.0°F (6.1°C)Light RainMostly SunnySlightly LowAverage
December36.5°F (2.5°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Woodstock

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Woodstock.
  • Consider traveling to Woodstock during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Woodstock Essential Information

Language
English
Currency
U.S dollars
Population
5,200
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Shenandoah River State Park, Shenandoah Vineyards and Cave Ridge Vineyard

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Frequently asked questions

How much does a Woodstock vacation package cost?
You can snap up a vacation package to this top destination from $357 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?
If you'd like to book a cheap Woodstock vacation package, consider visiting in November, December and January. You'll usually find better prices on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Woodstock?
You can easily explore all the main attractions in Woodstock within a few days, including the must-see Shenandoah County Fairgrounds. If you want a longer Woodstock vacation, look at what kind of day tours and activities are available nearby.
Is it worth booking a vacation package to Woodstock?
Woodstock is a good vacation destination with attractions like Shenandoah County Fairgrounds among the many things to keep you busy. Whether you're traveling with the family or planning a trip with friends, a Woodstock vacation promises a good time for everyone.
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.
Does Expedia offer Book Now, Pay Later Woodstock vacation packages?
Set off on your dream trip to Woodstock with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up travel deals while they last.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.