Sherando Vacations from $121

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Your Sherando Vacation

When a city getaway is calling, answer it with a Sherando vacation package. The neighborhood of Chestnut Springs, which is good for adventure sports, skiing and walking, makes an awesome base for your adventures. Fill your itinerary with tours of Swannanoa Palace, Ravens Roost Overlook and Humpback Rocks, some of the things you just have to see during a trip to Sherando. Don't delay your visit to this city any longer. Your ultimate Sherando vacation is only a few clicks away with Expedia.

The Latest Sherando vacation packages

Price found within the past 48 hours. Click for updated prices.
Suburban Studios Verona - Staunton North

Suburban Studios Verona - Staunton North

2 out of 5
Price was $140, price is now $121 per person
$121
per person
Feb 20 - Feb 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Weyers Cave (SHD)
7.2/10 Good! (98 reviews)
Good for the price.

Reviewed on Nov 22, 2025

Mountainside Villas at Massanutten by Tripforth

Mountainside Villas at Massanutten by Tripforth

3.5 out of 5
Price was $855, price is now $713 per person
$713
per person
Mar 19 - Mar 22
found 2 hours ago
Roundtrip flight included
Pensacola (PNS) to Weyers Cave (SHD)
9/10 Wonderful! (333 reviews)
Pros- Beautiful view, nice amenities such as jacuzzi anbs sauna) and plenty of space for a family to spread out. Cons- Cleaning could be better (laundry machine still had clumps of used detergent, hair on the floor and furniture) and some appliances are old and not working properly (coffee maker was leaking, microwave was glitching) minimal cookware and kitchen equipment.

Reviewed on Jan 2, 2026

Massanutten's Woodstone Meadows by Tripforth

Massanutten's Woodstone Meadows by Tripforth

4 out of 5
Price was $779, price is now $673 per person
$673
per person
Mar 4 - Mar 7
found 8 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Weyers Cave (SHD)
9/10 Wonderful! (219 reviews)
The room was spotless and hostesses were excellent .

Reviewed on Nov 6, 2025

Massanuttens Shenandoah Villas by Tripforth

Massanuttens Shenandoah Villas by Tripforth

4 out of 5
Price was $734, price is now $643 per person
$643
per person
Feb 27 - Mar 1
found 24 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Weyers Cave (SHD)
7.6/10 Good! (144 reviews)
Condo was clean. Jacuzzi tub needs updating. Everything else was good.

Reviewed on Dec 31, 2025

Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $672, price is now $590 per person
$590
per person
Mar 19 - Mar 22
found 2 hours ago
Roundtrip flight included
Pensacola (PNS) to Weyers Cave (SHD)
8.2/10 Very Good! (1,002 reviews)
A premier place to spend the night in comfort and quiet. Great location beautiful hotel

Reviewed on Jan 4, 2026

Don't see what you're looking for?
See all available trips from Columbus to Sherando
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Discover the most popular places to visit in Sherando

This was one of my favorite overlooks off of the Blue Ridge Parkway. Worth the stop!

Raven's Roost Overlook

Find out about the history of Wintergreen when you take a trip to Raven's Roost Overlook. Discover the mountain views and top-notch restaurants in this vibrant area.

Raven's Roost Overlook

Sherando Lake Recreation Area

Enjoy the mountain views and explore Sherando Lake Recreation Area, a lovely green space in Lyndhurst. While in this vibrant area, you can savor the top-notch restaurants.

Sherando Lake Recreation Area

What to do in Sherando

Old Rag Mountain

Shenandoah National Park Self-Guided Audio Tour

$16
per traveler
Shenandoah National Park Self-Guided Audio Tour
Shenandoah Lake

Blue Ridge Parkway Virginia Self-Guided Audio Tour

$13
per traveler
Blue Ridge Parkway Virginia Self-Guided Audio Tour
See all activities in Sherando

Sherando Hotel Deals

Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $125 total per night from Jan 25 to Jan 26
$125 total
Jan 25 - Jan 26
Total with taxes and fees
9.4/10 Exceptional! (1,073 reviews)
Outstanding staff and attention to details!

Reviewed on Jan 13, 2026

Hotel 24 South
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy Staunton VA
Fully refundable
$73 nightly
The price is $82 total per night from Feb 8 to Feb 9
$82 total
Feb 8 - Feb 9
Total with taxes and fees
9.2/10 Wonderful! (1,394 reviews)
Very clean

Reviewed on Jan 7, 2026

Sleep Inn Staunton
Quality Inn Verona - Staunton North

Quality Inn Verona - Staunton North

2.5 out of 5
70 Lodge Lane Verona VA
Fully refundableReserve now, pay when you stay
$62 nightly
The price is $69 total per night from Feb 3 to Feb 4
$69 total
Feb 3 - Feb 4
Total with taxes and fees
8/10 Very Good! (944 reviews)
Clean room courtesy of staff

Reviewed on Jan 10, 2026

Quality Inn Verona - Staunton North
See all 1,299 properties in Sherando
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.

Find the Best Sherando Vacation Packages

Sherando Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Charlottesville-Albemarle Airport (CHO)
Population
690
Top Sights
Ravens Roost Overlook, Sherando Lake Recreation Area and Humpback Rocks

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Frequently asked questions

How much does a Sherando vacation package cost?
Offering great value package deals from $121 on Expedia, you'll be pleasantly surprised at how much a vacation to Sherando costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Sherando?
You can typically find lower prices and better availability in December, January and February. Take a look at our cheap Sherando vacation packages and you could score some excellent off-season deals.
How many days is enough for Sherando?
With a well-planned itinerary, you can easily tick off the main Sherando attractions in a handful of days. But if you'd like to explore off the beaten track or take day trips, think about booking your Sherando vacation for longer.
How to find the best Sherando package deals?
Bagging a cheap Sherando package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most wallet-friendly Sherando package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Sherando vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Sherando vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Sherando?
Land incredible discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Sherando escape.
Does Expedia offer Book Now, Pay Later Sherando vacation packages?
Your Sherando trip is meant to be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.