Shenandoah Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Shenandoah

Country Inn & Suites by Radisson, Hagerstown, MD

Country Inn & Suites by Radisson, Hagerstown, MD

17612 Valley Mall Rd Hagerstown MD
S$143
30 Aug - 31 Aug
includes taxes & fees
8.6/10 Excellent! (1,311 reviews)
"Tout était parfait et déjeuner aussi, il y avait du choix"

Reviewed on 5 Aug, 2026

Country Inn & Suites by Radisson, Hagerstown, MD
Spark by Hilton Winchester

Spark by Hilton Winchester

150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
S$112
23 Aug - 24 Aug
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"It was a great place to stay for our vacation."

Reviewed on 5 Aug, 2026

Spark by Hilton Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

333 Front Royal Pike Winchester VA
Fully refundable
S$136
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
"Had to go back to desk 2 times after checking in while my wife stood outside our room with luggage in the hall because the keys didn't work. Very frustrating! Also, only 7 channels worked on the TV, was told this was Comcast fault."

Reviewed on 6 Aug, 2026

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 1,054 properties in Shenandoah
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.

Stay near popular Shenandoah attractions

Mill Creek

You can do some window-shopping at Mill Creek during your visit to Inwood. You can enjoy the restaurants while in the area.
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Darkesville Historic District

You can learn about the history of Inwood with a stop at Darkesville Historic District. You can enjoy the restaurants while in the area.
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Bunker Hill Historic District

You can find out about the history of Bunker Hill with a visit to Bunker Hill Historic District.
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Frequently asked questions

How much does a Shenandoah holiday package cost?
Live it up in Shenandoah from just . We offer a great selection of rental cars, hotels and flights to suit your budget. Score even more discounts when you add some experiences or tours to your holiday package.
How do I get a cheap travel package to Shenandoah?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Hotels, rental cars, flights and activities — we've got it all. Pick a combination that best fits you and watch your savings stack up. We know a package deal is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 hotels worldwide, which lets you customize your Shenandoah getaway.
What are the top hotels in Shenandoah?
Hampton Inn Martinsburg South-Inwood is one of Shenandoah's most popular hotels. Reserve a room here and you'll be able to snooze soundly knowing you're in good hands.
How far in advance should I book my Shenandoah holiday?
Savvy travellers book early. Air carriers usually release flight tickets up to 12 months prior to departure, and this is when you can land some rock-bottom prices. Just been told you should take your holiday time next week? Don't fret. Expedia are never short of fantastic deals to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Shenandoah travel package include?
Expedia has everything you need to lock in Shenandoah getaway, but how your package is structured is totally up to you. Select from a combination of rental cars, flights and hotels. After some activities or tours to keep you on the move? Once you've made your booking, you can add them on too. No matter your style, there's a package to suit your needs.
What should I know before booking a Shenandoah travel package?
Locking in all the parts of your getaway together is a terrific way to save. Bundle your car rentals, airfares and hotels into a tidy package. But your options don't end at hotels. Expedia features all kinds of properties, including holiday rentals like mountain cabins and city apartments. You've got choices galore!
Can I choose my airline with a Shenandoah Expedia holiday package?
You can, and with more than 550 airlines to select from around the world, it's all about choice. Have a look through the available options and find out which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my Shenandoah holiday package?
Your situation can change in the blink of an eye, so yes, you can. You may be able to cancel or amend your Shenandoah holiday package at no cost if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your airline, hotel or car rental company may impose a fee. Need more information? Look up our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.