Pine Ridge Vacation Packages 2026 from $479

Pine Ridge flight + hotel vacation packages

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

Comfort Inn Winchester

$479

per person

Oct 8 - Oct 12

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's dry cleaning and multilingual staff can provide around-the-clock assistance.

GuestHouse Lexington

$658

per person

Oct 8 - Oct 12

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

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

Home2 Suites by Hilton Lexington University / Medical Center

Zandale

$1,254

per person

Oct 8 - Oct 12

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the free continental breakfast each morning.

Holiday Inn Lexington - Hamburg by IHG

$817

per person

Oct 8 - Oct 12

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

This hotel features a restaurant, an indoor pool, and a bar/lounge. 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.

Hampton Inn I-75 Lexington/Hamburg Area

$864

per person

Oct 8 - Oct 12

found 4 hours ago

Roundtrip flight included

Chicago (ORD) to Lexington (LEX)

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

Top Pine Ridge hotels deals

TURNING LEAF•Cozy Cabin in the RRG• Couples Retreat

Pine Ridge KY

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

Kitchen

Pet friendly

• KNOTTY PINE•Cozy Cabin in RRG • Hot Tub • Fireplace • Pond for Fishing

Pine Ridge KY

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A hot tub is featured at this cabin, along with a garden and barbecue grills.

Hot Tub

Kitchen

Hikers Retreat• Handcrafted Cabin in RRG • PET FRIENDLY• Location is Key

Pine Ridge KY

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This cabin features barbecue grills.

Kitchen

Pet friendly

Secluded Cliffside Cabin Near Red River Gorge

Pine Ridge KY

$269 nightly

$296 total

Sep 9 - Sep 10

Total with taxes and fees

This cabin features barbecue grills.

Kitchen

Washer

Red River Gorge Cottage

Pine Ridge KY

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Stay at this cottage in Pine Ridge. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Natural Bridge State Park and Red River Gorge are located nearby.

Kitchen

Air conditioning

Cabin in RRG• Pet Friendly • Hi Speed 🛜 Hikers Welcome

Pine Ridge KY

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This cabin features barbecue grills.

Kitchen

Pet friendly

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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.

Frequently asked questions

How much are vacation packages to Pine Ridge?

With deals starting at just $479, 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.