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.
Ulysses, an Ash Hotel

Ulysses, an Ash Hotel

4 out of 5
Midtown
per person
Apr. 2 - Apr. 5
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (654 reviews)
Second time staying here and look forward to staying here again.

Reviewed on Jan. 22, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
per person
Apr. 2 - Apr. 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.2/10 Very Good! (1,005 reviews)
Pictures definitely helped this property in the choosing process. Hotel IRL was a disappointment. It was very outdated. Shower was dirty and water pressure weak. Even thought about leaving mid stay on the first night. Bed linen and pillows stained and dingy. TVs outdated with very little channels to choose from. For the price that was paid, the hotel and the stay did not seem to match the value. Hotel safe was nice and welcoming but would not return to this property.

Reviewed on Jan. 12, 2025

4206 Washington Blvd Condos

4206 Washington Blvd Condos

4 out of 5
Ballston
Save 100% on your flight
per person
Apr. 2 - Apr. 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
6/10 (2 reviews)
Placemakr Dupont Circle

Placemakr Dupont Circle

4 out of 5
Northwest
Save 100% on your flight
per person
Mar. 28 - Apr. 2
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Washington (DCA)
8.4/10 Very Good! (598 reviews)
This is a great place to base yourself for a short or extended stay in DC. It has lots of good eats and nightlife nearby and easy access to the metro

Reviewed on Jan. 15, 2025

Atlantic Sands Hotel & Conference Center

Atlantic Sands Hotel & Conference Center

3.5 out of 5
North Rehoboth
per person
Mar. 15 - Mar. 22
found 14 hours ago
Roundtrip flight included
Montreal (YUL) to Baltimore (BWI)
8.4/10 Very Good! (1,325 reviews)
Clean and convenient

Reviewed on Jan. 21, 2025

Ready to book your vacation to Woodstock?

 

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Woodstock Hotel Deals

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
The price is CA $161 per night from Jan. 28 to Jan. 29
CA $161
CA $180 total
includes taxes & fees
Jan 28 - Jan 29
8.8/10 Excellent! (1,001 reviews)
"Needs a better couch in the big suite."

Reviewed on Jan. 6, 2025

Hampton Inn & Suites Woodstock, VA
Comfort Inn Woodstock Shenandoah
Comfort Inn Woodstock Shenandoah
2.5 out of 5
1011 Motel Dr, Woodstock, VA
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Feb. 9 to Feb. 10
CA $128
CA $144 total
includes taxes & fees
Feb 9 - Feb 10
8.6/10 Excellent! (937 reviews)
Totally worth it
"Staff was friendly and very accommodating. The included breakfast was superb. Close proximity to a lot of things."

Reviewed on Jan. 13, 2025

Comfort Inn Woodstock Shenandoah
Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel
Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel
2.5 out of 5
1130 Motel Dr, Woodstock, VA
Fully refundable
The price is CA $143 per night from Feb. 9 to Feb. 10
CA $143
CA $160 total
includes taxes & fees
Feb 9 - Feb 10
9/10 Wonderful! (1,001 reviews)
"The property was well kept. The room was clean and comfortable. I was very pleased with this choice."

Reviewed on Jan. 17, 2025

Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel
See all 1,045 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Woodstock vacation package cost?
You can snap up a vacation package to this top destination from CA $546 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.