Woodstock Vacations from $450

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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.
Lord Baltimore Hotel

Lord Baltimore Hotel

Downtown Baltimore
Save 100% on your flight
$450
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (3,160 reviews)
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.
Save 100% on your flight
$530
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,012 reviews)
The River Inn

The River Inn

Northwest
Save 100% on your flight
$482
per person
Oct 19 - Oct 23
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (2,062 reviews)
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

Northwest
Save 100% on your flight
$466
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,586 reviews)
Lyle Washington D.C.

Lyle Washington D.C.

Northwest
Save 100% on your flight
$656
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,663 reviews)
Loved the beautiful neighborhood the hotel is situated in. The valet parking gentlemen were extremely nice and helpful. The room was very clean and the restaurant food was delicious. Overall a great experience in an exciting city.

Reviewed on Aug 11, 2026

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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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Woodstock Hotel Deals

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

Holiday Inn Express Woodstock-Shenandoah Valley by IHG

1130 Motel Dr Woodstock VA
Fully refundable
$97 nightly
$109 total
Sep 6 - Sep 7
Total with taxes and fees
9/10 Wonderful! (1,005 reviews)
"Easy check-in. Clean room. Soft linens. Friendly staff."

Reviewed on Aug 11, 2026

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

Comfort Inn Woodstock Shenandoah

1011 Motel Dr Woodstock VA
Fully refundableReserve now, pay when you stay
$92 nightly
$103 total
Aug 23 - Aug 24
Total with taxes and fees
8.8/10 Excellent! (1,013 reviews)
"Clean room easy parking good breakfast"

Reviewed on Aug 9, 2026

Comfort Inn Woodstock Shenandoah
Hampton Inn & Suites Woodstock, VA

Hampton Inn & Suites Woodstock, VA

1150 Motel Dr Woodstock VA
Fully refundableReserve now, pay when you stay
$106 nightly
$119 total
Aug 24 - Aug 25
Total with taxes and fees
Hampton Inn & Suites Woodstock, VA
See all 1,159 properties in Woodstock
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 $450 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.