Shenandoah Valley Vacation Packages

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Your Shenandoah Valley Vacation

Set off on your next adventure with a Shenandoah Valley vacation package, and leave relaxed knowing all the details have been taken care of. Plus with the ability to customize your escape, it'll be one to remember. With so much to see on a trip to Shenandoah Valley, it can be hard to know where to begin. Kick off your journey in Charlottesville at Monticello and Downtown Mall — two popular attractions here. Another great city worthy of a spot on your itinerary is Roanoke. Don't miss Berglund Centre and Valley View Mall. Whether you're planning to travel for a couple of days or a couple of weeks, Expedia are here to help you tailor-make your next dream Shenandoah Valley vacation.

Top Shenandoah Valley Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was CA $1,576, price is now CA $1,130 per person
CA $1,130
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.6/10 Excellent! (1,000 reviews)
The property is very nice unfortunately the night staff need to be more helpful when we reported things missing in the room like towels no one came up I call twice to the front desk to then be told I had to go down and get it my self other wise nice place to stay

Reviewed on Jul 7, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,096, price is now CA $1,403 per person
CA $1,403
per person
Sep 17 - Sep 21
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.6/10 Exceptional! (81 reviews)
The staff made the trip feel like I was welcomed and mattered! Absolutely would recommend!

Reviewed on Jul 5, 2026

Element by Marriott Arundel Mills BWI Airport

Element by Marriott Arundel Mills BWI Airport

3 out of 5
Arundel Mills
Price was CA $1,729, price is now CA $1,170 per person
CA $1,170
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,003 reviews)
Didn’t like that room service wasn’t available during my visit. Other than that the location was perfect!

Reviewed on Jul 5, 2026

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was CA $1,874, price is now CA $1,309 per person
CA $1,309
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (2,841 reviews)

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,813, price is now CA $1,275 per person
CA $1,275
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
6/10 (1 review)

Where to stay in Shenandoah Valley

Find the best Shenandoah Valley areas and neighborhoods for the activities you enjoy most. Learn more about Shenandoah Valley
An aerial view of a campus with multiple buildings surrounded by green fields and trees.

North Downtown

1 out of top 10 points of interest in this area
5/5(1 area review)

If you're spending some time in North Downtown, Paramount Theater and Downtown Mall are top sights worth seeing.

Find hotels in North Downtown

Ready to book your vacation to Shenandoah Valley?

 

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Shenandoah Valley Hotel Deals

Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Jul 23 to Jul 24
CA $106
CA $120 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"

Reviewed on Jul 5, 2026

Spark by Hilton Winchester
Spark by Hilton Roanoke Airport

Spark by Hilton Roanoke Airport

3 out of 5
3695 Thirlane Rd Nw Roanoke VA
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Jul 27 to Jul 28
CA $115
CA $131 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (452 reviews)
"A good hot breakfast was advertised but all they had was a bagel bar. Room had a weird humid smell. The bed smelled like stale playdoh. They charged for parking (which they did not mention before hand) despite having a huge parking lot. There were a lot of bees outside in the front parking area which ..."

Reviewed on Jul 7, 2026

Spark by Hilton Roanoke Airport
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is CA $129 per night from Jul 19 to Jul 20
CA $129
CA $144 total
Jul 19 - Jul 20
includes taxes & fees
TRU By Hilton Winchester
See all 5,948 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.
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Stay near popular Shenandoah Valley attractions

A waterfall in a forest with autumn foliage.

Shenandoah National Park

9.4/10 (322 reviews)
Blue ridges fill your view as you gaze over the many acres of tree-covered wilderness in this peaceful Virginia park.
See properties

What to do in Shenandoah Valley

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

CA $34
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

CA $24
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

CA $18
per traveller
Blue Ridge Parkway Virginia Self-Guided Audio Tour
See all activities in Shenandoah Valley

Frequently asked questions

How much does a Shenandoah Valley vacation package cost?
Maybe less than you imagined — from a tempting CA $1,130, actually! By combining hotels, flights and car rentals into a custom-built vacation package, your getaway to Shenandoah Valley is just clicks away.
How do I get a cheap travel package to Shenandoah Valley?
Simply by bundling. Flights, rental cars and hotels — combine whatever you need into a Shenandoah Valley vacation package to save tons of cash. Score even bigger bargains when you include extras such as experiences or tours to your booking. But that's not the only impressive part. You have the flexibility to put together your trip your own way. We offer over 550 airlines and 1,000,000 hotels worldwide, so that everyone has a chance to travel and live out those vacation fantasies.
Where should I stay in Shenandoah Valley?
To see terrific attractions such as Monticello and University of Virginia, Charlottesville is the place to be. Plenty of travelers also adore Roanoke, home to Mill Mountain Star and Center in the Square. If you've got an extended vacation in Shenandoah Valley, why not visit both cities?
What are the top hotels in Shenandoah Valley?
When it comes to properties in Nellysford, Days Inn by Wyndham Roanoke Near I-81 and Country Inn & Suites by Radisson, Charlottesville-UVA, VA are two great options. If you're also heading to McGaheysville, Hilton Vacation Club The Historic Powhatan Williamsburg and Holiday Inn National Airport/Crystal City, an IHG Hotel will make you feel at home.
How far in advance should I book my Shenandoah Valley vacation?
It's tricky picking the perfect time for airfares, but we generally say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you're unable to do so, don't despair. Discounted prices appear from time to time just weeks before departure dates.
What does an Expedia Shenandoah Valley travel package include?
Hotels, flights and car rentals — we connect you to the very best deals. All you'll have to do is pick your favorite combination. After you've made your booking, you can add on the exciting stuff like day tours and sightseeing activities. Our travel packages make it simple to put together an awesome Shenandoah Valley escape.
What should I know before booking a Shenandoah Valley travel package?
Whether it's adventure or relaxation you're chasing, a Shenandoah Valley vacation package lets you plan your escape your way. Plus, you'll score great discounts just for combining your hotel with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with a Shenandoah Valley Expedia vacation package?
Yes — that's the beauty of an Expedia vacation package. You get to decide. We have access to more than 550 airline partners across the globe, so you have loads of choice when putting together your Shenandoah Valley trip.
If I'm not able to travel, can I cancel my Shenandoah Valley vacation package?
If your travel plans in Shenandoah Valley have changed, it's comforting to know that it's possible to cancel or amend your booking. If your booking was made within the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose fees. For more information, visit our Customer Service Portal.

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