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.
Hotel Nell - Union Market

Hotel Nell - Union Market

3 out of 5
Northeast
per person
May 9 - May 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.2/10 Very Good! (489 reviews)
Fair, slightly lass good than expected for the price

Reviewed on Mar. 30, 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
Jun. 4 - Jun. 11
found 10 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
8.2/10 Very Good! (1,010 reviews)
Great location Nice service

Reviewed on Mar. 30, 2025

Airlie Hotel

Airlie Hotel

3.5 out of 5
Save 100% on your flight
per person
Jun. 20 - Jun. 27
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Washington (DCA)
8.8/10 Excellent! (280 reviews)
This place is beautiful and amazing. Better than expected. We had a stay.

Reviewed on Mar. 30, 2025

The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Northwest
Save 100% on your flight
per person
Jun. 4 - Jun. 11
found 10 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
8.6/10 Excellent! (1,094 reviews)
Great hotel. Restaurant was delicious. Staff was very helpful. The room was huge. Almost the size of a 1 bedroom apartment. I loved it.

Reviewed on Mar. 31, 2025

La Quinta Inn & Suites by Wyndham Washington DC / NoMa

La Quinta Inn & Suites by Wyndham Washington DC / NoMa

2.5 out of 5
Northeast
Save 100% on your flight
per person
Jun. 4 - Jun. 11
found 10 hours ago
Roundtrip flight included
Montreal (YMQ) to Washington (DCA)
7/10 Good! (104 reviews)
Excellent service!! Very clean ! 5 stars !

Reviewed on Mar. 30, 2025

Ready to book your vacation to Woodstock?

 

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Woodstock Hotel Deals

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 $134 per night from Apr. 13 to Apr. 14
CA $134
CA $150 total
includes taxes & fees
Apr 13 - Apr 14
8.6/10 Excellent! (971 reviews)
"Comfortable bed, friendly staff. Nice hot shower in the morning. Free breakfast doesn't open till 7 am which is a little late for those of us who are traveling."

Reviewed on Mar. 29, 2025

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
The price is CA $148 per night from Apr. 20 to Apr. 21
CA $148
CA $166 total
includes taxes & fees
Apr 20 - Apr 21
8.8/10 Excellent! (1,001 reviews)
"Friend clued us in to ask for a room not on the highway side.....hotel provides ear plugs because sound is annoying. Apparently highway built after the hotel"

Reviewed on Mar. 28, 2025

Hampton Inn & Suites Woodstock, VA
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
The price is CA $153 per night from Apr. 6 to Apr. 7
CA $153
CA $172 total
includes taxes & fees
Apr 6 - Apr 7
9/10 Wonderful! (1,000 reviews)
Holiday
"Great stay"

Reviewed on Mar. 23, 2025

Holiday Inn Express Woodstock-Shenandoah Valley by IHG
See all 1,059 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 $751 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.