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.
Viceroy Washington DC

Viceroy Washington DC

4.5 out of 5
Downtown Washington D.C.
per person
Jan. 3 - Jan. 5
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.2/10 Wonderful! (896 reviews)
We just wrapped up a four night stay at Viceroy in DC. Nothing but good things to say about this hotel - excellent, walkable location tucked on a quiet leafy side street with easy access to everything; amazing service from the staff and restaurant/cafe; hip vibes while not feeling pretentious; delicious in room espresso and tea; well equipped fitness room; modern, chic design and amenities. Would definitely come back and will consider the Viceroy brand in other cities in the future, for sure.

Reviewed on Nov. 22, 2024

Ocean Glass Inn

Ocean Glass Inn

3.5 out of 5
West Rehoboth
Save 100% on your flight
per person
Jan. 1 - Jan. 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.6/10 Exceptional! (971 reviews)
The Staff was great and the property was very clean! Diffinetly a dimmond in the rough!

Reviewed on Nov. 3, 2024

The Bellmoor Inn & Spa

The Bellmoor Inn & Spa

4 out of 5
South Rehoboth
per person
Jan. 1 - Jan. 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (983 reviews)
You can walk anywhere in downtown Rehoboth. It wouldn’t be necessary to move your car unless you wanted to.

Reviewed on Nov. 19, 2024

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
per person
Jan. 23 - Jan. 26
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.2/10 Wonderful! (1,004 reviews)
Beautiful property, very close to Wharf dining options.

Reviewed on Nov. 13, 2024

The Gallery Unit 301

The Gallery Unit 301

3.5 out of 5
Old Town Alexandria
per person
Dec. 24 - Dec. 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Washington (DCA)
No reviews
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until December 4 with our Black Friday deals. Stay by December 15, 2025.
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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 $153 per night from Dec. 23 to Dec. 24
CA $153
CA $172 total
includes taxes & fees
Dec 23 - Dec 24
8.8/10 Excellent! (1,001 reviews)
"Property was close to where I needed to go."

Reviewed on Nov. 20, 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 $154 per night from Dec. 1 to Dec. 2
CA $154
CA $173 total
includes taxes & fees
Dec 1 - Dec 2
9/10 Wonderful! (1,000 reviews)
"Just an over night but it was good I"

Reviewed on Nov. 16, 2024

Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel
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 $105 per night from Dec. 9 to Dec. 10
CA $105
CA $117 total
includes taxes & fees
Dec 9 - Dec 10
8.6/10 Excellent! (905 reviews)
"Property is a little outdated but clean and comfortable. Miriam at the Front Desk was very pleasant and helpful."

Reviewed on Nov. 17, 2024

Comfort Inn Woodstock Shenandoah
See all 1,032 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?
Our Woodstock vacation packages, which begin from just CA $594, are an ideal way to save money. All you have to do is choose your preferred hotels, flights and rental car to create your dream escape.
How do I get a cheap travel package to Woodstock?
Combining your flight and hotel with Expedia won’t just save valuable time — it’ll save you a tidy sum too. A Woodstock vacation package makes it a cinch to organize your dream adventure. With more than 550 airlines all over the world to select from, finding flights that fit your busy schedule won’t be a hassle. On top of that, we have over 1,000,000 properties globally to choose from. Now that’s what you call choice. Whatever your budget, Expedia can show you the world.
Where should I stay in Woodstock?
With lots to discover in Woodstock, it’s a good idea to lock in a hotel near its attractions. Shenandoah County Fairgrounds, Woodstock Museum and Seven Bends State Park are some fascinating ones to add to your to-do list.
What are the top hotels in Woodstock?
Get your vacation off to an excellent start by reserving a room at Comfort Inn Woodstock Shenandoah. It’s one of most sought-after properties in Woodstock. Another cozy option is Holiday Inn Express Woodstock-Shenandoah Valley, an IHG Hotel.
How far in advance should I book my Woodstock vacation?
Travelers are normally able to compare international fares on Expedia up to a year in advance of departure. Booking late? With a little bit of luck, it’s still possible to score a cheaper ticket just weeks before your journey.
What does an Expedia Woodstock travel package include?
You can select from a combination of flights, hotels and rental cars. Once you’ve made your booking, you can add some experiences and activities. Want to pick your airfare class? That’s also easy to do. The choice is yours when it comes to putting together your perfect Woodstock escape.
What should I know before booking a Woodstock travel package?
A package can be cheaper than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save a tidy sum. Whatever your vacation goals are, there’s sure to be a package that suits your budget.
Can I choose my airline with a Woodstock Expedia vacation package?
With a vacation package, you’re the boss. Whether you’d like to fly to Woodstock in first class or coach, simply pick from the available airline options. Expedia has access to more than 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Woodstock vacation package?
Whether it’s your hotel or flight, yes, you can cancel or amend it. Locked in your Woodstock vacation package in the last 24 hours? You may be able to make changes or cancellations at no cost. For older bookings, you may incur a fee from your hotel, airline or car rental company. For more details, visit our Customer Service Portal. We’re here to help you every step of the way.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.