Dillwyn Vacations from $515

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Your Dillwyn Vacation

The adventure-filled city of Dillwyn is calling. Uncover both its hidden gems and highlights with a Dillwyn vacation package that's custom made for you. Your trip to Dillwyn wouldn't be complete without exploring its top attractions, like Buckingham Historic Village. Whoever you're taking time off with and whether your budget is big or small, your dream Dillwyn vacation is just a few clicks away with Expedia.

The Latest Dillwyn 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 $643, price is now $515 per person
$515
per person
Mar 24 - Mar 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.2/10 Wonderful! (281 reviews)
Room was amazing, loved the records and record player. Very cozy!

Reviewed on Feb 15, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $746, price is now $601 per person
$601
per person
Mar 24 - Mar 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.2/10 Wonderful! (517 reviews)
Beautiful artistic room and friendly service

Reviewed on Feb 14, 2026

The Doyle Hotel

The Doyle Hotel

3.5 out of 5
Starr Hill
Price was $626, price is now $526 per person
$526
per person
Mar 24 - Mar 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
8.6/10 Excellent! (944 reviews)
Room was clean and quiet, my email directions on unlocking the room door were incomplete- it said to use a hashtag following the code and there was no hashtag on the door lock! Finally tried other symbols and the check mark worked. The water did not heat up the first night so had to wash up with cold water. It worked the last day thankfully. Staff very friendly but not always around.

Reviewed on Feb 21, 2026

The Draftsman, Charlottesville, University, Autograph Collection Hotel

The Draftsman, Charlottesville, University, Autograph Collection Hotel

4 out of 5
10th and Page
Price was $740, price is now $640 per person
$640
per person
Mar 24 - Mar 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.4/10 Exceptional! (323 reviews)
All of the above! Everyone was wonderful

Reviewed on Feb 17, 2026

Keswick Hall

Keswick Hall

5 out of 5
Price was $1,593, price is now $1,379 per person
$1,379
per person
Mar 24 - Mar 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Charlottesville (CHO)
9.4/10 Exceptional! (62 reviews)
Everyone and everything was wonderful

Reviewed on Apr 14, 2025

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Dillwyn Hotel Deals

Hotel Weyanoke

Hotel Weyanoke

3.5 out of 5
202 High Street Farmville VA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $117 total per night from Mar 4 to Mar 5
$117 total
Mar 4 - Mar 5
Total with taxes and fees
9.2/10 Wonderful! (1,001 reviews)
Great stay, great location.

Reviewed on Feb 18, 2026

Hotel Weyanoke
Holiday Inn Express & Suites Farmville by IHG

Holiday Inn Express & Suites Farmville by IHG

2.5 out of 5
404 Sunchase Blvd Farmville VA
Fully refundable
$100 nightly
The price is $112 total per night from Mar 8 to Mar 9
$112 total
Mar 8 - Mar 9
Total with taxes and fees
9.2/10 Wonderful! (635 reviews)
Clean room and friendly staff.

Reviewed on Feb 9, 2026

Holiday Inn Express & Suites Farmville by IHG
Tru by Hilton Farmville

Tru by Hilton Farmville

2.5 out of 5
1913 South Main Street Farmville VA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $119 total per night from Mar 1 to Mar 2
$119 total
Mar 1 - Mar 2
Total with taxes and fees
8.6/10 Excellent! (709 reviews)
Everything was perfect as always

Reviewed on Feb 19, 2026

Tru by Hilton Farmville
See all 63 properties in Dillwyn
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 Dillwyn Vacation Packages

Dillwyn Essential Information

Language
English
Currency
U.S dollars
Population
450
Top Sights
Bear Creek Lake State Park and Buckingham Historic Village

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Frequently asked questions

How much does a Dillwyn vacation package cost?
You'll find cheap prices from $515 on Expedia for your Dillwyn break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Dillwyn costs.
What are the cheapest months to go to Dillwyn?
If you're hoping to book a cheap Dillwyn vacation package, consider visiting in November, December and January. You'll typically find better prices on hotels and airfares during these months — perfect for travelers wishing to save money.
How many days is enough for Dillwyn?
Usually, a handful of days is enough to go to the top sights during your Dillwyn vacation. However, if you want to have some time to unwind or take day tours, consider extending your itinerary.
How to find the best Dillwyn package deals?
Begin your search for a Dillwyn package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Dillwyn package deal right away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Dillwyn adventure off to a flying start.
Is it cheaper to book a Dillwyn vacation as a package?
You can enjoy significant savings on your next Dillwyn retreat by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Dillwyn?
If you're planning a spontaneous Dillwyn vacation, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Dillwyn vacation packages?
Your Dillwyn break is meant to be an escape from your daily routine, not a source of money-related stress. So to allow you a bit 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 cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs 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.