Howardsville Vacations from $527

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The Latest Howardsville vacation packages

Price found within the past 48 hours. Click for updated prices.
The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $630, price is now $527 per person
$527
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
8.6/10 Excellent! (944 reviews)
Not much staff when we were there, as it was not busy, but they were excellent. Feel like the place would have a great vibe on a busy college weekend. Room layout was great. Enjoyed our stay and would recommend, for sure. Don't know if our travels will take us there again, but would definitely choose the Doyle for another stay.

Reviewed on Jan 26, 2026

Mayhurst Inn

Mayhurst Inn

3.5 out of 5
Save 100% on your flight
Price was $826, price is now $620 per person
$620
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.2/10 Wonderful! (288 reviews)
A perfect spot with the delicious breakfast. Highly recommend staying here.

Reviewed on Sep 4, 2025

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $802, price is now $643 per person
$643
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.2/10 Wonderful! (517 reviews)
Our room was clean and the staff was super friendly and courteous. We did hope that our room had a microwave and refrigerator. It makes sense to have that available in every room on the grounds. Guests I’m sure would appreciate it. Please consider doing this. Lastly, we could here noises above us from possibly furniture that wasn’t secure. Footsteps are understandable, but the rattle of something above room 5 was a bit annoying. This is probably an eat fix. Overall the property was safe, clean and convenient.

Reviewed on Jan 1, 2026

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $754, price is now $619 per person
$619
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
New York (NYC) 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

Virginia Guesthouse At University Of Virginia

2 out of 5
Lewis Mountain
Price was $920, price is now $760 per person
$760
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
No reviews
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Howardsville Hotel Deals

Holiday Inn Charlottesville-Monticello by IHG

Holiday Inn Charlottesville-Monticello by IHG

3 out of 5
1200 5th St. SW Charlottesville VA
Fully refundable
$93 nightly
The price is $106 total per night from Jan 29 to Jan 30
$106 total
Jan 29 - Jan 30
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Room is clean and comfortable. The staff at the front desk was extra helpful and friendly!

Reviewed on Jan 22, 2026

Holiday Inn Charlottesville-Monticello by IHG
Sleep Inn & Suites Monticello

Sleep Inn & Suites Monticello

2.5 out of 5
1185 5th St SW Charlottesville VA
Fully refundable
$82 nightly
The price is $94 total per night from Feb 20 to Feb 21
$94 total
Feb 20 - Feb 21
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
Breakfast good

Reviewed on Jan 11, 2026

Sleep Inn & Suites Monticello
Wow! What A View!

Wow! What A View!

Wintergreen Resort VA
9.8/10 Exceptional! (54 reviews)
Beautiful retreat to the mountains over the holidays! The condo was a perfect spot for us. Spacious & cozy for our family of 4 (included 2 teenage boys). The condo was very clean & nice accomodations which included firewood & a large balcony w/ an incredible view of the mountains & Wintergreen ski ...

Reviewed on Jan 2, 2026

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Wow! What A View!
See all 871 properties in Howardsville
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 Howardsville Vacation Packages

Howardsville Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Howardsville vacation package cost?
You can pick up a vacation package to this top destination from $527 on Expedia. But how much your vacation to Howardsville costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Howardsville?
November, December and January are great times to search for cheap Howardsville vacation packages. Opting to travel in quieter months means you can generally find reduced prices on flights and accommodations.
How many days is enough for Howardsville?
Generally, a handful of days is enough to go to the top attractions during your Howardsville vacation. But if you prefer to have more time to chill out or take day trips, think about extending your trip.
How to find the best Howardsville package deals?
Bagging a cheap Howardsville package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most wallet-friendly Howardsville package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Howardsville vacation as a package?
You can enjoy significant savings on your Howardsville escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to browse some great flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Howardsville?
Secure fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Howardsville break.
Does Expedia offer Book Now, Pay Later Howardsville vacation packages?
Your Howardsville break is meant to be an escape from your daily routine, not a source of money-related stress. So to give you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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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.