Prestonsburg Vacation Packages 2026 from $590

Prestonsburg flight + hotel vacation packages

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

The Delegate

$590

per person

Jul 29 - Aug 2

found 12 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking and express check-out are also offered on site.

21c Museum Hotel Lexington

Downtown Lexington

$637

per person

Aug 7 - Aug 12

found 9 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a 24-hour business center, and a snack bar/deli are also offered.

Capital Plaza Hotel

$595

per person

Aug 6 - Aug 11

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

This hotel features a restaurant, an indoor pool, and a bar/lounge. There's a gym on site, and laundry facilities and concierge services are also offered.

Origin Lexington a Wyndham Hotel

$652

per person

Aug 7 - Aug 12

found 9 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Lexington (LEX)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Free self parking and a coffee shop are also offered on site.

Marriott Lexington Griffin Gate Golf Resort & Spa

$647

per person

Aug 7 - Aug 12

found 9 hours ago

Roundtrip non-stop flight included

Milwaukee (MKE) to Lexington (LEX)

This luxury resort features a golf course, a full-service spa, and a restaurant. Traveling on business? Take advantage of the 24-hour business center, express check-in, and valet parking. Enjoy the indoor pool and perks like free self parking.

Top Prestonsburg hotels deals

Comfort Suites Prestonsburg West

51 Hal Rogers Dr Prestonsburg KY

Free Cancellation

$110 nightly

$124 total

Jul 12 - Jul 13

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.

Pool

Breakfast included

Quality Inn & Suites Prestonsburg next to Mountain Arts Center

85 Hal Rogers Drive Prestonsburg KY

Free Cancellation

$99 nightly

$112 total

Jul 9 - Jul 10

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

Super 8 by Wyndham Prestonsburg

80 Shoppers Path Prestonsburg KY

Get rates

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. The front desk is staffed around-the-clock and free newspapers are on offer.

Breakfast included

Pet friendly

Luxury Estate nestled atop stunning mountaintop golf course!

Prestonsburg KY

Get rates

This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Cozy Home in Heart of Prestonsburg

Prestonsburg KY

$157 nightly

$178 total

Jul 1 - Jul 2

Total with taxes and fees

This vacation home features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

Near Scenic Parks: Convenient Home in Prestonsburg

Prestonsburg KY

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This vacation home features laundry facilities.

Kitchen

Washer

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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.

Popular places to visit

Jenny Wiley State Resort Park

4.5/5(20 reviews)

Explore the great outdoors at Jenny Wiley State Resort Park, a lovely green space in Prestonsburg. Wander the riverfront or discover the area's mountain views.

StoneCrest Golf Course

4.5/5(5 reviews)

Enjoy a round of golf in Prestonsburg at StoneCrest Golf Course. Stroll along the riverfront or discover the area's mountain views.

Middle Creek National Battlefield

4/5(2 reviews)

Middle Creek National Battlefield is just one of the places to see in Prestonsburg, so why not enjoy the other things to explore during your travels? Amble around the area's riverfront or experience its live music.

Frequently asked questions

How much are vacation packages to Prestonsburg?

Travelocity offers great package deals to Prestonsburg, including flights and hotels, from an impressive $590. With all the money you save, you could book some interesting tours or perhaps even tack on a couple of extra nights to your vacation.

How long should my Prestonsburg vacation be?

There are no strict rules for how long your Prestonsburg vacation should be, but many travelers stay for around 3 nights. Got some leeway with your travel dates? Consider booking a couple more nights. Then you'll have time to explore some lesser-known areas too.

Where can I get the best vacation package deals for Prestonsburg?

You can lock in amazing Prestonsburg package deals with Travelocity. Mix and match from 400 partner airlines and 1,000,000 properties worldwide and turn those vacation dreams into reality.

Why should I book my Prestonsburg vacation bundle with Travelocity?

The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to 24/7 customer support. With the Travelocity Price Match Guarantee, you can rest easy knowing you're getting the best deal available.

Will I save money on my Prestonsburg car rental if I book it with a hotel or flight?

Bundling your car, flight and hotel into a Prestonsburg vacation package is a surefire way to land the best prices. Plus, having your own set of wheels gives you absolute freedom to find your way to all those big sights you can't wait to see. Situated 55 mi from Prestonsburg, Paramount Arts Center is one attraction that should be on your must-do list. Put together a driving playlist and make a day trip of it.

Which airport is best for Prestonsburg?

A flight to Prestonsburg means landing at Tri-State Airport (HTS). It's roughly 50 mi north of the downtown area.

What is there to do in Prestonsburg?

There is a certain magic in the air as you stroll the streets of Prestonsburg. Jenny Wiley State Resort Park and Mountain Arts Center are just a couple of famous attractions that make this city such a sought-after destination, so add them to your travel itinerary.

Where should I stay when visiting Prestonsburg?

If you're looking for a place to spend your nights, have a look at the Comfort Suites Prestonsburg West. It's the top choice for many visitors.