Boonesville Vacations from $553

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Your Boonesville Vacation

Take the hassle out of travel planning with a Boonesville vacation package. A great neighborhood to base yourself in this amazing city is Advance Mills, which is great for history and much more. Glass House Winery and Stone Mountain Vineyards are just two of the must-see sights to visit during your trip to Boonesville. Don't put off visiting this destination any longer. The perfect Boonesville vacation is just a few clicks away with Expedia.

The Latest Boonesville vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
Price was $643, price is now $553 per person
$553
per person
Mar 5 - Mar 8
found 10 hours ago
Roundtrip non-stop flight included
San Diego (SAN) 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

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $858, price is now $699 per person
$699
per person
Mar 5 - Mar 8
found 10 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Charlottesville (CHO)
9.6/10 Exceptional! (320 reviews)
If you’re looking for a one-of-a-kind place to stay filled with history and charm, this is it. It’s right in the heart of everything UVA, yet it feels like stepping back in time—without giving up any modern comforts. Jake was incredible to work with—he was flexible with our schedule, made sure we always knew where to go, and communicated better than anyone I’ve worked with before. Thank you so much for your hospitality. We will definitely stay here again and recommend it to everyone.

Reviewed on Jan 12, 2026

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $729, price is now $594 per person
$594
per person
Mar 5 - Mar 8
found 10 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Charlottesville (CHO)
8.2/10 Very Good! (823 reviews)
The staff was lovely and so were the rooms, the lake and the horses. The restaurant serves tasty food with large portions

Reviewed on Nov 19, 2025

Shenandoah Wilderness Traveler

Shenandoah Wilderness Traveler

2 out of 5
Price was $725, price is now $591 per person
$591
per person
Mar 5 - Mar 8
found 10 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Charlottesville (CHO)
8.6/10 Excellent! (65 reviews)
Great place for a recess!

Reviewed on Dec 3, 2025

Boar's Head Resort

Boar's Head Resort

4 out of 5
Ednam
Price was $943, price is now $797 per person
$797
per person
Mar 5 - Mar 8
found 10 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Charlottesville (CHO)
9/10 Wonderful! (1,003 reviews)
The resort was amazing and went over and above. Can’t speak high enough about the staff!!

Reviewed on Jan 18, 2026

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Discover the most popular places to visit in Boonesville

Glass House Winery

4.5/5(2 reviews)

You can enjoy a tasting or tour at Glass House Winery during your travels to Free Union. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Glass House Winery

What to do in Boonesville

Memorable and exciting Vineyard in Virginia

Private Wine Tours (Minimum 3 & Maximum 6 ) Pickup Maximum 30 Mi

$118
per adult
100% of travellers recommend
Private Wine Tours (Minimum 3 & Maximum 6 ) Pickup Maximum 30 Mi
See all activities in Boonesville

Boonesville Hotel Deals

Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$130 nightly
The price is $144 total per night from Jan 28 to Jan 29
$144 total
Jan 28 - Jan 29
Total with taxes and fees
8/10 Very Good! (1,197 reviews)
I would hve liked

Reviewed on Jan 13, 2026

Massanutten Resort
Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
212 Ridge McIntire Rd Charlottesville VA
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $164 total per night from Jan 25 to Jan 26
$164 total
Jan 25 - Jan 26
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
Was beautiful and clean. Good food.

Reviewed on Jan 15, 2026

Omni Charlottesville Hotel
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $101 total per night from Feb 16 to Feb 17
$101 total
Feb 16 - Feb 17
Total with taxes and fees
9.2/10 Wonderful! (2,709 reviews)
Wonderful staff

Reviewed on Jan 19, 2026

English Inn of Charlottesville
See all 1,336 properties in Boonesville
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 Boonesville Vacation Packages

Boonesville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Charlottesville-Albemarle Airport (CHO)

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Frequently asked questions

How much does a Boonesville vacation package cost?
Offering great value package deals from $553 on Expedia, you'll be surprised at how little a vacation to Boonesville costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Boonesville?
If you're looking to book a cheap Boonesville vacation package, consider planning a trip in November, December and January. You'll usually find lower prices on accommodations and flights during these months — ideal for budget-conscious travelers.
How many days is enough for Boonesville?
The ideal duration for your Boonesville vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to visit all the leading sights and explore some hidden gems along the way.
How to find the best Boonesville package deals?
Finding a cheap Boonesville package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Boonesville package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Boonesville vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalize your Boonesville getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Boonesville?
If you've got your Boonesville travel dates locked in, book as soon as you can to grab some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for impromptu escapes.
Does Expedia offer Book Now, Pay Later Boonesville vacation packages?
If you're like us, you love exploring new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Boonesville break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.