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.
Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Inner Harbor
per person
Jan. 24 - Jan. 31
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.4/10 Very Good! (319 reviews)
Great location! Walkable to everything in the Inner Harbor area. Close parking-garage fee was $36 for 24 hours.

Reviewed on Dec. 22, 2024

Ulysses, an Ash Hotel

Ulysses, an Ash Hotel

4 out of 5
Midtown
per person
Feb. 12 - Feb. 19
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
9/10 Wonderful! (609 reviews)
This hotel was like stepping back in time like, but modernized where it counts. I felt like I was in a movie from old days. Comfy bed, good shower, views, all good.

Reviewed on Dec. 20, 2024

Kimpton Hotel Monaco Baltimore Inner Harbor, an IHG Hotel

Kimpton Hotel Monaco Baltimore Inner Harbor, an IHG Hotel

4.5 out of 5
Downtown Baltimore
per person
Feb. 11 - Feb. 16
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
8/10 Very Good! (1,003 reviews)
Upon entering our room, we noticed that we had no hot water. A quick call to the front desk resulted in a prompt response and we were moved in a matter of minutes. The restaurant at the hotel came highly recommended and we enjoyed a wonderful meal. My advice….order the crab cakes!!! Delicious.

Reviewed on Dec. 14, 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
per person
Mar. 7 - Mar. 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (1,520 reviews)
I loved the property and its proximity to M St & Wisconsin Ave, the main streets in Georgetown. Their checkin is not until 4pm which hindered our ability to get to our function, but the property, room with a balcony, rooftop & speakeasy bars were great!

Reviewed on Dec. 19, 2024

Hotel 24 South

Hotel 24 South

3 out of 5
per person
Feb. 15 - Feb. 22
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Weyers Cave (SHD)
9.4/10 Exceptional! (1,003 reviews)
Great clean and quiet

Reviewed on Dec. 22, 2024

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 Jan. 12 to Jan. 13
CA $134
CA $151 total
includes taxes & fees
Jan 12 - Jan 13, 2025
8.6/10 Excellent! (921 reviews)
"It was good"

Reviewed on Dec. 21, 2024

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 $157 per night from Dec. 29 to Dec. 30
CA $157
CA $177 total
includes taxes & fees
Dec 29 - Dec 30
8.8/10 Excellent! (1,002 reviews)
"Braden at the front desk is awesome. The guy is respectful, polite, kind and knowledgeable. Talk about having a gem for an employee. People like him will enhance any business they work for because they have the qualities and drive to succeed."

Reviewed on Dec. 22, 2024

Hampton Inn & Suites Woodstock, VA
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 Dec. 29 to Dec. 30
CA $143
CA $161 total
includes taxes & fees
Dec 29 - Dec 30
9/10 Wonderful! (1,000 reviews)
"Hotel was very quiet and overall a great stay. The bathroom had some stains in it from Water. Functionally it was fine, just visually was a little offputting. I stay at this hotel 3 to 4 times a year coming back home from Florida. I would recommend it overall."

Reviewed on Dec. 17, 2024

Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel
See all 1,035 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 $792 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.