Pine Ridge Vacation Packages 2025/2026 from $570

Pine Ridge flight + hotel vacation packages

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

Days Inn by Wyndham Paintsville

$570

per person

Jan 5 - Jan 11

found 14 hours ago

Roundtrip non-stop flight included

Chicago (MDW) to Lexington (LEX)

This motel 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. Enjoy the outdoor pool and conveniences like a 24-hour front desk and laundry facilities.

Ramada Hotel & Conference Center by Wyndham Paintsville

$686

per person

Jan 5 - Jan 11

found 14 hours ago

Roundtrip non-stop flight included

Chicago (MDW) to Lexington (LEX)

This hotel features an outdoor pool, an indoor pool, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

Super 8 by Wyndham Prestonsburg

$595

per person

Jan 5 - Jan 11

found 14 hours ago

Roundtrip non-stop flight included

Chicago (MDW) to Lexington (LEX)

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.

Holiday Inn Express Hotel & Suites Pikeville by IHG

$761

per person

Jan 5 - Jan 11

found 14 hours ago

Roundtrip non-stop flight included

Chicago (MDW) to Lexington (LEX)

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 buffet breakfast and free self parking.

Comfort Suites Prestonsburg West

$712

per person

Jan 5 - Jan 11

found 14 hours ago

Roundtrip non-stop flight included

Chicago (MDW) to Lexington (LEX)

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.

Top Pine Ridge hotels deals

Turning Leaf Cabin in the Red River Gorge• Pet Friendly• Hi Speed 🛜

Pine Ridge KY

Get rates

This cabin includes free WiFi in public areas and barbecue grills.

Kitchen

Pet friendly

WiFi & Pet Friendly - The Road`s End

Pine Ridge KY

Get rates

A hot tub is featured at this cabin, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.

Hot Tub

Kitchen

Three bedroom in United States of America, Pine Ridge

Pine Ridge KY

Get rates

A hot tub is featured at this vacation home, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.

Hot Tub

Kitchen

Natural Bridge State Resort Park

2135 Natural Bridge Road Slade KY

$86 nightly

$95 total

Dec 6 - Dec 7

Total with taxes and fees

This cabin features a restaurant, a seasonal outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area is provided and the front desk is staffed around-the-clock.

Pool

Breakfast included

Black Bear Lodge Motel

781 Natural Bridge Rd Slade KY

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$97 total

Nov 23 - Nov 24

Total with taxes and fees

This motel features a coffee shop, barbecue grills, and free self parking. A convenience store and a picnic area are also provided.

Parking included

Air conditioning

Oak Tree Inn

1075 Richmond Rd Irvine KY

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$98 total

Nov 22 - Nov 23

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Pet friendly

Parking included

Don't see what you're looking for?

See all available properties in Pine Ridge

View all properties

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.

Frequently asked questions

How much are vacation packages to Pine Ridge?

With deals starting at just $570, flight and hotel packages are an excellent way to make your budget stretch further. Get ready Pine Ridge — here you come!

How long should my Pine Ridge vacation be?

Around 3 nights is the average time frame visitors spend in Pine Ridge. But the ideal trip length depends on how many unforgettable memories you want to create. Why not stay a few extra days and explore some hidden treasures?

Where can I get the best vacation package deals for Pine Ridge?

You'll find sensational Pine Ridge package deals with Travelocity. Pick and choose from as many as 400 partner airlines and 1,000,000 properties worldwide and turn those vacation daydreams into a reality.

Why should I book my Pine Ridge vacation package with Travelocity?

From amazing destinations to fun experiences, we have everything you need to satisfy your wanderlust. Our friendly 24/7 customer support will also make sure you're being well taken care of before, during and after your getaway. And don't stress if you find a better price on your reservation, we'll match it. That's our Price Match Guarantee.

Will I save money on my Pine Ridge car rental if I bundle it with hotels and flights?

With a Pine Ridge vacation package, you can bundle your hotel, car and flight bookings and save a nice amount. When you're ready to discover the best of this impressive region, why not check out Churchill Downs? This popular sight is 120 mi from Pine Ridge. With a rental car, you'll be there in a jiffy.

Which airport is best for Pine Ridge?

Blue Grass Airport (LEX), the major terminal in Pine Ridge, is where you'll step off the plane. You'll find it 55 mi west of the downtown area.

Where should I stay when visiting Pine Ridge?

Many people opt to hit the hay at the Treetop Modern Cabin with Hot Tub, Creek View. It's an excellent base for your Pine Ridge vacation.