Prestonsburg Vacations from $526

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Your Prestonsburg Vacation

There's plenty to like about Prestonsburg, from its historical landmarks to its spectacular views. When you're ready to say hi to this lively city, our Prestonsburg vacation packages will be perfect for you. You'll want to do a little exploring during your trip to Prestonsburg. Don't miss famous attractions like Jenny Wiley State Resort Park, Mountain Arts Center and East Kentucky Science Center and Planetarium. Whoever you're heading away with and whatever you want to spend, your dream Prestonsburg vacation is just a few clicks away with Expedia.

The Latest Prestonsburg vacation packages

Price found within the past 48 hours. Click for updated prices.
Mountain View Inn Irvine Near Richmond KY

Mountain View Inn Irvine Near Richmond KY

2.5 out of 5
Price was $651, price is now $526 per person
$526
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
5.8/10 (33 reviews)
Absolutely terrible I slept in my car

Reviewed on Jul 23, 2026

Ramada Hotel & Conference Center by Wyndham Paintsville

Ramada Hotel & Conference Center by Wyndham Paintsville

2.5 out of 5
Price was $914, price is now $734 per person
$734
per person
Oct 19 - Oct 26
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Lexington (LEX)
8.8/10 Excellent! (596 reviews)

DoubleTree Suites by Hilton Hotel Lexington

DoubleTree Suites by Hilton Hotel Lexington

4 out of 5
Price was $1,326, price is now $1,089 per person
$1,089
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
8.8/10 Excellent! (1,005 reviews)
Close to where I needed to be.

Reviewed on Jul 31, 2026

Montgomery Inn BnB

Montgomery Inn BnB

4 out of 5
Price was $1,076, price is now $889 per person
$889
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.4/10 Exceptional! (113 reviews)
The host was very friendly and Sadie (dog) was adorable

Reviewed on Jul 30, 2026

Elwood Hotel & Suites

Elwood Hotel & Suites

4 out of 5
Price was $1,622, price is now $1,349 per person
$1,349
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Lexington (LEX)
9.4/10 Exceptional! (1,124 reviews)

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Stay near popular Prestonsburg attractions

Jenny Wiley State Resort Park

8.6/10 (92 reviews)
Nestled in the Appalachians, this park offers serene lakeside recreation and historical significance. Experience Broadway-style shows at Jenny Wiley Theatre or explore hiking trails with stunning mountain vistas.
See properties

Prestonsburg Hotel Deals

Comfort Suites Prestonsburg West

Comfort Suites Prestonsburg West

2.5 out of 5
51 Hal Rogers Dr Prestonsburg KY
Fully refundable
$110 nightly
The price is $124 total per night from Aug 23 to Aug 24
$124 total
Aug 23 - Aug 24
Total with taxes and fees
Comfort Suites Prestonsburg West
Spark by Hilton Prestonsburg

Spark by Hilton Prestonsburg

2 out of 5
80 Shoppers Path Prestonsburg KY
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Aug 10 to Aug 11
$93 total
Aug 10 - Aug 11
Total with taxes and fees
8/10 Very Good! (2 reviews)
"Clean and had everything for a pleasant stay, nothing exceptional, reflected a lower cost option."

Reviewed on Aug 1, 2026

Spark by Hilton Prestonsburg
Quality Inn & Suites Prestonsburg next to Mountain Arts Center

Quality Inn & Suites Prestonsburg next to Mountain Arts Center

2.5 out of 5
85 Hal Rogers Drive Prestonsburg KY
Fully refundable
$102 nightly
The price is $116 total per night from Aug 23 to Aug 24
$116 total
Aug 23 - Aug 24
Total with taxes and fees
8/10 Very Good! (397 reviews)
"The 2nd and 3rd floor are former smoking rooms that still have the horrible stench of the smoke. The 1st room I was in had a cracked window that I felt was unsafe. The 2nd room was a former smoke room. My 3rd room was back on the 1st floor with a horrible smelling desk chair....like sweat, body odor. ..."

Reviewed on Jul 20, 2026

Quality Inn & Suites Prestonsburg next to Mountain Arts Center
See all 100 properties in Prestonsburg
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 Prestonsburg Vacation Packages

Prestonsburg Essential Information

Language
English
Currency
U.S dollars
Population
3,300
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
East Kentucky Science Center and Planetarium, StoneCrest Golf Course and Archer Park

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Frequently asked questions

How much does a Prestonsburg vacation package cost?
Offering excellent value package deals from $526 on Expedia, you'll be thrilled with how little a vacation to Prestonsburg costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Prestonsburg?
You can generally find reduced prices and better availability in January, September and October. Browse our cheap Prestonsburg vacation packages and you could land some excellent off-season deals.
How many days is enough for Prestonsburg?
With about 2 days, you'll have plenty of time to experience popular neighborhoods like Dwale and Auxier during your Prestonsburg vacation. Make sure to also add Archer Park and Samuel May House to your must-see list. Searching for more adventures? Consider venturing outside of Prestonsburg on day trips and tours.
Is it worth booking a vacation package to Prestonsburg?
Boasting a host of highlights starting with its excellent walking trails, Prestonsburg is a good vacation destination. Whether you'd like to visit sights such as Mountain Arts Center and StoneCrest Golf Course or take the path less traveled, you'll find plenty to see and do on your Prestonsburg vacation.
How to find the best Prestonsburg package deals?
Begin your search for a Prestonsburg package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add 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 discover offers that come with irresistible savings. If you don't find the perfect Prestonsburg package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Prestonsburg escape off to a flying start.
Is it cheaper to book a Prestonsburg vacation as a package?
You can enjoy significant savings on your Prestonsburg escape by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Prestonsburg?
Enjoy incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Prestonsburg break.
Does Expedia offer Book Now, Pay Later Prestonsburg vacation packages?
If you're like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Prestonsburg 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 spot them.

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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.