Shenandoah Vacation Packages 2026 from $521

Shenandoah flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Little Mod Hotel at the University

Venable

$521

per person

Dec 18 - Dec 21

just found

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This hotel features a restaurant, free WiFi in public areas, and a picnic area. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Express check-in and express check-out are also provided.

Dinsmore Boutique Inn

Venable

$725

per person

Dec 18 - Dec 21

just found

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, concierge services, and wedding services are also on offer.

Oakhurst Inn at the University

Jefferson Park Avenue

$536

per person

Dec 18 - Dec 21

just found

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the sauna and conveniences like a 24-hour front desk and concierge services.

Virginia Guesthouse Hotel

Lewis Mountain

$531

per person

Dec 18 - Dec 21

just found

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This hotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a snack bar/deli are also on offer.

Boar's Head Resort

Ednam

$582

per person

Dec 18 - Dec 21

just found

Roundtrip flight included

Chicago (ORD) to Charlottesville (CHO)

This luxury hotel features a golf course, a full-service spa, and 2 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 3 outdoor pools and perks like free self parking and free WiFi.

Top Shenandoah hotels deals

Gorgeous Cabin Overlooking The Shenandoah River - 2 bedrooms ~ 2 lofts

Shenandoah VA

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This cabin features barbecue grills.

Kitchen

Pet friendly

River Pines Retreat! Cozy 4-bedroom cabin on the Shenandoah River.

Shenandoah VA

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A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.

Hot Tub

Washer

The Great Escape - Near everything yet off the beaten path

Shenandoah VA

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A hot tub is featured at this cabin, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Hot Tub

Kitchen

Bears Den - A Taste of Heaven from a Bearly Rustic Point of View

Shenandoah VA

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A hot tub is featured at this cabin, along with laundry facilities and barbecue grills.

Hot Tub

Kitchen

Massanutten Resort

1822 Resort Dr McGaheysville VA

$109 nightly

$120 total

Oct 25 - Oct 26

Total with taxes and fees

This hotel features a golf course, a full-service spa, and 4 restaurants. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy snowboarding. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities.

Pool

Hot Tub

Hotel Madison & Shenandoah Conference Ctr

710 S. Main Street Harrisonburg VA

$139 nightly

$156 total

Oct 25 - Oct 26

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Pool

Free WiFi

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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

Shenandoah Speedway

You can take time to visit Shenandoah Speedway during your travels to Shenandoah. While you're in the area, stroll along the riverfront.

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Frequently asked questions

How much are vacation packages to Shenandoah?

With vacation packages available from just $521, you won't need to drain your bank balance to travel to Shenandoah. Travelocity is here to help. Bundle experiences, flights and hotels into a convenient package and receive some serious discounts. The more you book, the more you save.

How long should my Shenandoah vacation be?

Most visitors stay in Shenandoah for roughly 3 nights. But travel is all about finding new adventures and making memories — why not book a couple of extra nights so you can do just that?

Where can I get the best vacation package deals for Shenandoah?

Travelocity will be able to help you get a Shenandoah package deal. With 400 partner airlines and 1,000,000 properties worldwide, we're sure you'll be able to put together the perfect itinerary.

Why should I purchase my Shenandoah vacation bundle via Travelocity?

Travel should be about making cherished new memories and leaving all your stresses behind — which is why we provide you with a team of experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our broad range of destinations. So what are you waiting for? There's no time like the present to secure that vacation you've always dreamed of.

Can I save money on my Shenandoah car rental if I combine it with hotels and flights?

Combining your flight, car and hotel into a Shenandoah vacation package is a great way to score the best deal. Plus, having your own car rental gives you absolute freedom to find your way to all those amazing sights you're hoping to check out. Sitting 90 mi away from Shenandoah, White House is one place that should be on your must-do list. Fasten your seat belt and make a day trip of it.

Which airport is best for Shenandoah?

Charlottesville-Albemarle Airport (CHO) is the gateway to your Shenandoah getaway. Situated 25 mi south of Shenandoah, it welcomes travelers from all over every day. Your other option is Shenandoah Valley Regional Airport (SHD), 20 mi away from central Shenandoah.

Where should I stay when visiting Shenandoah?

Many travelers spend their nights at the Cozy Cabin Retreat - Hot tub - Fire Pit - Game Room - 4 King Bedrooms. It's sure to be a good base for your Shenandoah getaway.