Woodstock Vacations from $247

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
Price was $421, price is now $247 per person
$247
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8/10 Very Good! (968 reviews)
People camping on the medium strip between highways. Stranger in front of hotel door cornered me and talked for over 30 minutes when all I wanted to do is get in my room and chill.

Reviewed on Aug 18, 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Save 100% on your flight
Price was $1,118, price is now $588 per person
$588
per person
Sep 26 - Oct 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
9.4/10 Exceptional! (1,012 reviews)
The Wharf is a beautiful area of DC. This hotel is very nice, fancy yet understated. Our room was clean, large and comfortable. Valet parking was a plus. Walkable to great restauranta and to The Anthem. A great concert venue. Our stay was lovely.

Reviewed on Aug 18, 2025

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $1,081, price is now $638 per person
$638
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
this was a well-priced hotel and we found it to be cute and homey- sort of like you were at a beach hotel. Happy vibes:)

Reviewed on Aug 17, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $617, price is now $372 per person
$372
per person
Oct 29 - Nov 1
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (WAS)
8.6/10 Excellent! (1,005 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on Aug 12, 2025

DoubleTree by Hilton Hotel Laurel

DoubleTree by Hilton Hotel Laurel

4 out of 5
West Laurel
Save 100% on your flight
Price was $575, price is now $356 per person
$356
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
Nonsmoking room smells like pot

Reviewed on Aug 20, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Woodstock

Shenandoah County Fairgrounds

4.5/5(23 reviews)

Take the family on an outing to Shenandoah County Fairgrounds during your trip to Woodstock. While you're here, you can savor the top-notch restaurants.

Shenandoah County Fairgrounds

Woodstock Museum

5/5(1 review)

You can spend time studying the exhibits at Woodstock Museum during your travels in Woodstock. While you're here, you can savor the top-notch restaurants.

Woodstock Museum

Woodstock Tower Observation Site

You can find out about the history of Woodstock with a visit to Woodstock Tower Observation Site. While in this vibrant area, you can savor the top-notch restaurants.

Woodstock Tower Observation Site

Woodstock Hotel Deals

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
$110 nightly
The price is $124 total per night from Aug 31 to Sep 1
$124 total
Aug 31 - Sep 1
Total includes taxes and fees
9/10 Wonderful! (1,000 reviews)
"It was quiet and clean"

Reviewed on Aug 18, 2025

Holiday Inn Express Woodstock-Shenandoah Valley by IHG
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
$99 nightly
The price is $112 total per night from Sep 15 to Sep 16
$112 total
Sep 15 - Sep 16
Total includes taxes and fees
8.8/10 Excellent! (1,005 reviews)
"Está bien para dormir una noche"

Reviewed on Aug 16, 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
$98 nightly
The price is $110 total per night from Sep 14 to Sep 15
$110 total
Sep 14 - Sep 15
Total includes taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Disappointed that we left message that we needed another bath towel and no response or towel. AC unit was draining water on the carpet in front of the unit. had to watch out you didn't step in front of it. advised front desk when we checked out. staff was friendly and breakfast was very good."

Reviewed on Aug 12, 2025

Comfort Inn Woodstock Shenandoah
See all 1,084 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.

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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 $247 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.