Shenandoah Valley Holidays

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Our pick of the best Shenandoah Valley Hotel Deals

A Pet-Friendly Oasis surrounded by wineries with a Pool, Jacuzzi, and Sauna.

A Pet-Friendly Oasis surrounded by wineries with a Pool, Jacuzzi, and Sauna.

Plymouth
9.8/10 Exceptional! (191 reviews)
With six private bedrooms, five with en-suite bathrooms, this property was perfect for our varied family members while attending a nearby wedding.

Reviewed on 23 Oct 2025

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A Pet-Friendly Oasis surrounded by wineries with a Pool, Jacuzzi, and Sauna.
Charming Amador Farmhouse! Located on the Shenandoah Valley Wine Trail.

Charming Amador Farmhouse! Located on the Shenandoah Valley Wine Trail.

Plymouth
10/10 Exceptional! (64 reviews)
Beautiful historic farmhouse
Modernized historic farmhouse in a beautiful location! We thoroughly enjoyed relaxing around the gas fireplace on the wrap around patio at the end of the day. The host was very responsive and helpful, going above and beyond to make our stay memorable. The kitchen was well stocked with items you would ...

Reviewed on 17 July 2025

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Charming Amador Farmhouse! Located on the Shenandoah Valley Wine Trail.
Wine Lovers Retreat Amidst Shenandoah Valley with Pool

Wine Lovers Retreat Amidst Shenandoah Valley with Pool

2 out of 5
Plymouth
10/10 Exceptional! (10 reviews)
The house and pool house were great for our large group. We enjoyed the fire pit and outdoor seating and really loved being able to walk to Paul J winery right next door. We will come again!

Reviewed on 20 Oct 2025

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Wine Lovers Retreat Amidst Shenandoah Valley with Pool
See all 417 properties in Shenandoah Valley
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.

Frequently asked questions

How much does a Shenandoah Valley holiday package cost?
From as low as , you can tailor make your Shenandoah Valley holiday package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Shenandoah Valley?
You'll save loads of cash if you bundle your car rentals, flights and hotels into a Shenandoah Valley holiday package. Sometimes cheap means fewer options. But that's not the case with Expedia. We offer over 550 air carriers and 1 000 000 properties throughout the world, so you'll always have plenty of options to choose from. Eager to save even more? Add some fun activities to your package deal and unlock even more discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Shenandoah Valley?
If you plan to check out Andis Wines, save yourself the hassle of commuting and book a hotel room nearby. It's one of the top attractions in this area.
What are the top hotels in Shenandoah Valley?
Book a room at Plymouth Villa With Working Vineyard And Private Pool. It's one of this area's most in-demand hotels. Another highly rated option in Shenandoah Valley is Pet Friendly Next To Amador Top Wineries.
How far in advance should I book my Shenandoah Valley holiday?
It can be hard to know exactly when is the perfect time to book your Shenandoah Valley trip. But usually the earlier you book, the lower the prices. In some cases, you can book your flights and hotels up to 12 months prior to departure. If you're hoping for a last-minute getaway, no need to fret! There are fantastic bargains posted on Expedia all the time.
What does an Expedia Shenandoah Valley travel package include?
That depends on what you're after. If you're travelling alone, you might decide to combine flights and hotels. Taking the entire family to Shenandoah Valley? A travel package including flights, hotels and rental cars might be a better fit. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Shenandoah Valley travel package?
When you book your hotels, flights and car rentals together, you'll nab incredible discounts. Whether you're organising a rural escape in a cottage or want to stay in an upscale city hotel, Expedia can help make it happen.
Can I choose my airline with a Shenandoah Valley Expedia holiday package?
Yes, you can. We have more than 550 airline partners globally, so go with the carrier that matches your needs.
If I'm not able to travel, can I cancel my Shenandoah Valley holiday package?
If your holiday plans in Shenandoah Valley have been upended, it's good to know that it's possible to cancel or amend your booking. If you made your booking within the last 24 hours, you may be able to get a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a fee. For more information, visit our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.