Woodstock Holidays from £896

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Your Woodstock Holiday

Our Woodstock holiday packages let you customise 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 holiday plans in motion!

Top Woodstock Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Washington DC - Crystal City

DoubleTree by Hilton Washington DC - Crystal City

4 out of 5
Crystal City
Price was £1,058, price is now £896 per person
£896
per person
25 Dec - 1 Jan
found 9 hours ago
Return flight included
London (LHR) to Baltimore (BWI)
8.4/10 Very good! (1,589 reviews)
Room clean and staff very helpful will come back

Reviewed on 10 Nov 2026

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

5 out of 5
Northwest
Price was £1,653, price is now £1,337 per person
£1,337
per person
28 Dec - 2 Jan
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
9.6/10 Exceptional! (1,005 reviews)
Excellent experience - can’t wait to return

Reviewed on 9 Nov 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £1,454, price is now £1,196 per person
£1,196
per person
12 Dec - 16 Dec
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)
Rooms were short on closet space and no dressers to put clothes for an 8 day stay

Reviewed on 9 Nov 2026

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Price was £2,025, price is now £1,673 per person
£1,673
per person
28 Dec - 2 Jan
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
9.8/10 Exceptional! (1,001 reviews)

Hilton Garden Inn Arlington/Courthouse Plaza

Hilton Garden Inn Arlington/Courthouse Plaza

3 out of 5
Radnor - Fort Myer Heights
Price was £1,061, price is now £898 per person
£898
per person
25 Dec - 1 Jan
found 9 hours ago
Return flight included
London (LHR) to Baltimore (BWI)
8.8/10 Excellent! (1,219 reviews)

Woodstock Essential Information

Language
English
Currency
U.S dollars
Population
5,200
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Shenandoah River State Park, Shenandoah Vineyards and Cave Ridge Vineyard

Top hotels in Woodstock

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 £75 per night from 29 Nov to 30 Nov
£75
29 Nov - 30 Nov
includes taxes & fees
Holiday Inn Express Woodstock-Shenandoah Valley by IHG
Comfort Inn Woodstock Shenandoah

Comfort Inn Woodstock Shenandoah

2.5 out of 5
1011 Motel Dr Woodstock VA
Fully refundable
The price is £78 per night from 22 Nov to 23 Nov
£78
22 Nov - 23 Nov
includes taxes & fees
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 £85 per night from 7 Dec to 8 Dec
£85
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Breakfast could be better"

Reviewed on 28 Oct 2026

Hampton Inn & Suites Woodstock, VA
See all 1,209 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Woodstock attractions

Shenandoah County Fairgrounds

9.0/10 (48 reviews)
The Shenandoah County Fairgrounds hosts the valley's oldest fair, drawing thousands with agricultural exhibits and harness races. Experience local traditions, entertainment, and regional cuisine during late August.
See properties

Frequently asked questions

Why should I book my Woodstock holiday with Expedia?
Expedia has your back for every detail of your upcoming Woodstock holiday. You'll always land the best deals around, but when you bundle your flights, hotel and/or hire car into a holiday package, you can save even more. Want to truly make the most of your escape? Add some tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so there's no need to stress if you have to change your plans. Visit our Customer Service Portal link to learn more.
When is the best time of year to holiday in Woodstock?
Woodstock can get very busy in April, May and August, so if you want to escape the crowds, visit in November, December and January. Arrange your visit to Woodstock based on what style of holiday you want. January is the coolest time of year, when average daytime temperatures are 0ºC. In July, the warmest month, you can expect temperatures of around 23ºC during the day.
What is the top hotel for my holiday in Woodstock?
Offering plenty of amenities and a cosy place to relax between adventures, Hyatt Place Herndon Dulles Airport East will make the perfect base for your Woodstock escape.
How do I get a cheap holiday to Woodstock?
Booking a Woodstock holiday with Expedia is an easy way to save. We have over 400 partner airlines and 321,000 hotels around the globe. With such an awesome range to choose from, you'll have no trouble putting together your ideal getaway. Learn more about how you can save money on your next holiday when you book a flight and hotel together with Expedia.
What should I do on my Woodstock holiday?
Offering major attractions like Shenandoah County Fairgrounds and Shenandoah Vineyards, a holiday in Woodstock is filled with fun places to visit. Woodstock Museum and Secret Passage Ranch are two other sights also worth a look.
What is the best area to stay in when on holiday in Woodstock?
If you plan to check out Shenandoah County Fairgrounds, save yourself the hassle of commuting and lock in a stay nearby. It's one of the best attractions in Woodstock.
Do I need a visa for my Woodstock holiday?
Official government websites have all the information you need on visa requirements, application procedures and any necessary documentation. Your nationality and purpose for visiting, whether it be for tourism or business, will determine if you'll need a visa for Woodstock. Also check that your passport is up to date and has a minimum of six months validity remaining beyond the date of your return. Do all your travel planning ahead of time to avoid any nasty last-minute surprises.
What should I wear on my Woodstock holiday?
Do a little research into the sorts of things people in Woodstock wear, and maybe even look up fashion pages on social media for inspiration. Whatever your look, aim to create a versatile wardrobe filled with pieces that work for your destination and showcase your personal style. Daytime temperatures during January, Woodstock's coolest month, average 0ºC. July marks this city's warmest month when the average temperature reaches 23ºC. Our top tip? Take the guesswork out of packing and check the local weather conditions.
What does an Expedia Woodstock holiday include?
Expedia has everything you need to arrange your Woodstock trip, but how your package is structured is your call. Pick from any combination of hotels, hire cars and flights. Looking for some tours or experiences to keep you on the move? Once you've made your booking, you can add them too. Whatever your style or budget, there's a package to meet your needs. Expedia features all types of properties, with the most popular in Woodstock being private holiday homes and hotels. With Expedia, you can expect the flexibility and freedom to tailor-make your holiday your way.
Does Expedia offer Book Now, Pay Later Woodstock holidays?
Your bank balance shouldn't get in the way of going on holiday, so Expedia has devised a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a terrific getaway without drying up your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's convenient instalment plans. If paying in multiple instalments sounds right for you, pick this option during the checkout process.
  • No-deposit holidays: When you see an amazing deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.

Can I choose my airline with a Woodstock Expedia holiday?
Yes, the choice is all yours. We offer more than 400 airlines around the world, so you can customise your Woodstock adventure according to your budget and travel needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.