Boonesville Vacations from $391

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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.
The Blackburn Inn and Conference Center

The Blackburn Inn and Conference Center

3.5 out of 5
Price was $444, price is now $391 per person
$391
per person
Oct 13 - Oct 17
found 4 hours ago
Roundtrip flight included
Tampa (TPA) to Weyers Cave (SHD)
9.2/10 Wonderful! (1,000 reviews)
What a gem. A beautiful historic building close to downtown shopping & dining and loved my room’s high ceiling & wood floors. Great wi fi connection. Very quiet!

Reviewed on Sep 8, 2025

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $1,045, price is now $788 per person
$788
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Charlottesville (CHO)
9.6/10 Exceptional! (305 reviews)
Dinsmore Boutique Inn is everything you'd expect from a small inn -- lovely, spacious, well-appointed rooms, and wonderful management. We were made to feel welcome the entire time, from check-in to delicious breakfasts to helpful advice.

Reviewed on Sep 1, 2025

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $990, price is now $805 per person
$805
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Charlottesville (CHO)
8.6/10 Excellent! (899 reviews)
Spot is great, close to everything and nice views from their rooftop bar!

Reviewed on Sep 2, 2025

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $1,013, price is now $870 per person
$870
per person
Oct 10 - Oct 12
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Charlottesville (CHO)
9.2/10 Wonderful! (248 reviews)
Everything was great.

Reviewed on Sep 9, 2025

Mountainside Villas at Massanutten by Tripforth

Mountainside Villas at Massanutten by Tripforth

3.5 out of 5
Price was $491, price is now $433 per person
$433
per person
Oct 13 - Oct 17
found 4 hours ago
Roundtrip flight included
Tampa (TPA) to Weyers Cave (SHD)
9/10 Wonderful! (330 reviews)
Simply amazing definitely doing this again.

Reviewed on Sep 2, 2025

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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

$95
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

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 Oct 1 to Oct 2
$101 total
Oct 1 - Oct 2
Total with taxes and fees
English Inn of Charlottesville
Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr, McGaheysville, VA
$114 nightly
The price is $126 total per night from Sep 10 to Sep 11
$126 total
Sep 10 - Sep 11
Total with taxes and fees
Massanutten Resort
Extended Stay America Premier Suites - Charlottesville

Extended Stay America Premier Suites - Charlottesville

2.5 out of 5
3400 Berkmar Drive, Charlottesville, VA
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $94 total per night from Sep 21 to Sep 22
$94 total
Sep 21 - Sep 22
Total with taxes and fees
Extended Stay America Premier Suites - Charlottesville
See all 1,222 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.

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Frequently asked questions

How much does a Boonesville vacation package cost?
Offering great value package deals from $391 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.