Mount Sidney Vacations from $364

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Your Mount Sidney Vacation

Skip the stress of planning your next great adventure with a Mount Sidney vacation package. Whether you've come for its food, entertainment or something else, there's an inexhaustible array of experiences to be had. When the time comes to venture out and explore, be sure to include Factory Antique Mall and Augusta Military Academy Museum on the itinerary for your trip to Mount Sidney. That dream Mount Sidney vacation is clicks away. Search flights, accommodations and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Mount Sidney vacation packages

Price found within the past 48 hours. Click for updated prices.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $476, price is now $364 per person
$364
per person
Jun 21 - Jun 24
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (332 reviews)
Best experience for our 1 night stay. Loved the vibe!!!

Reviewed on May 14, 2026

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $1,190, price is now $847 per person
$847
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Charlottesville (CHO)
9.6/10 Exceptional! (383 reviews)
no elevator to 2nd floor room. clean, parking OK and good breakfast

Reviewed on May 16, 2026

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

2 out of 5
Lewis Mountain
Price was $522, price is now $393 per person
$393
per person
Jun 21 - Jun 24
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
9/10 Wonderful! (14 reviews)
I would’ve given this hotel five stars, had I been charged their normal rack rates. It’s brand new, beautiful, and has an extremely friendly and professional staff. Unfortunately, at nearly $1000 per night on graduation weekend, it raises the expectations and the hotel does not meet that price category of property. It’s a clearly cashing in on a captive audience but seems to be a common theme in the area. That said, as long as you avoid the gauging times, this is an excellent hotel near UVA.

Reviewed on May 18, 2026

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $563, price is now $429 per person
$429
per person
Jun 21 - Jun 24
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
8.4/10 Very Good! (1,003 reviews)
The hotel is beautiful - sleek and chic! Great location and stellar staff. The rooftop bar and restaurant is my favorite place in Charlottesville. (The gluten-free pizza is FANTASTIC!). The rooms are nice, but there was mildew on the shower walls the last 2 times we stayed there. The gym has some broken equipment, but that won't stop us from coming back! The best value in the area.

Reviewed on May 8, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $973, price is now $770 per person
$770
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Charlottesville (CHO)
9.2/10 Wonderful! (559 reviews)
Clean room. Comfortable beds.

Reviewed on May 8, 2026

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Mount Sidney Hotel Deals

Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$119 nightly
The price is $131 total per night from May 21 to May 22
$131 total
May 21 - May 22
Total with taxes and fees
8/10 Very Good! (1,321 reviews)
"Easy stay for jmu graduation!"

Reviewed on May 19, 2026

Massanutten Resort
Sleep Inn Staunton

Sleep Inn Staunton

2.5 out of 5
222 Jefferson Hwy Staunton VA
Fully refundable
$97 nightly
The price is $108 total per night from May 31 to Jun 1
$108 total
May 31 - Jun 1
Total with taxes and fees
9.2/10 Wonderful! (1,433 reviews)
"This is the second time we've stayed here. We occasionally need to be close to Augusta Valley Health facilities. This will now be our go-to spot for that. It's been newly renovated and was very well done. It's always clean, and staff are very friendly and helpful. (Jamie is especially top notch!) ..."

Reviewed on May 20, 2026

Sleep Inn Staunton
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $119 total per night from May 27 to May 28
$119 total
May 27 - May 28
Total with taxes and fees
9.6/10 Exceptional! (1,128 reviews)
"Fantastic location in the heart of Staunton. We watched a play at the next door Shakespearean style theatre & ate the best ribs of our lives at the Mill Street Grill. Would happily stay here again."

Reviewed on May 18, 2026

Hotel 24 South
See all 1,224 properties in Mount Sidney
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 Mount Sidney Vacation Packages

Mount Sidney Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Shenandoah Valley Regional Airport (SHD)
Top Sights
American Shakespeare Center, Grand Caverns and Cross Keys Vineyards

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Frequently asked questions

How much does a Mount Sidney vacation package cost?
You can pick up a vacation package to this popular destination from $364 on Expedia. However, how much your vacation to Mount Sidney costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Mount Sidney?
You can typically find reduced prices and better availability in November, December and January. Browse our cheap Mount Sidney vacation packages and you could score some great off-season discounts.
How many days is enough for Mount Sidney?
With a well-organized travel plan, you can easily visit the top Mount Sidney sights in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Mount Sidney vacation for longer.
How to find the best Mount Sidney package deals?
Begin your search for a Mount Sidney package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Mount Sidney package deal straight away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Mount Sidney adventure off to a flying start.
Is it cheaper to book a Mount Sidney vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Mount Sidney vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Mount Sidney?
Land incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Mount Sidney trip.
Does Expedia offer Book Now, Pay Later Mount Sidney vacation packages?
Jet off on your dream escape to Mount Sidney with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.