Pine Ridge Vacations from $559

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The Latest Pine Ridge vacation packages

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

Montgomery Inn BnB

4 out of 5
Price was $655, price is now $559 per person
$559
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Lexington (LEX)
9.4/10 Exceptional! (110 reviews)
Yes

Reviewed on Jun 14, 2026

21c Museum Hotel Lexington

21c Museum Hotel Lexington

4 out of 5
Downtown Lexington
Price was $967, price is now $820 per person
$820
per person
Aug 31 - Sep 4
just found
Roundtrip flight included
Philadelphia (PHL) to Lexington (LEX)
8.8/10 Excellent! (1,000 reviews)
It’s in a historical landmark building so I get that it’s old. But the tile floors were pretty dingy looking. The corners in the rooms seemed to be overlooked when cleaned. Very convenient location to bars and restaurants. Staff was great.

Reviewed on Jun 25, 2026

Wildflower Ranch Inn

Wildflower Ranch Inn

3.5 out of 5
Price was $1,088, price is now $951 per person
$951
per person
Aug 31 - Sep 5
found 4 hours ago
Roundtrip flight included
Philadelphia (PHL) to Lexington (LEX)
9.2/10 Wonderful! (23 reviews)
Beautiful historic property run by two artists who are great hosts. Conveniently located to many Bourbon Trail stops. The master’s suite with the whirlpool tub is incredible.

Reviewed on Apr 18, 2026

Origin Lexington a Wyndham Hotel

Origin Lexington a Wyndham Hotel

3.5 out of 5
Price was $1,058, price is now $935 per person
$935
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Lexington (LEX)
9.4/10 Exceptional! (1,008 reviews)
The hotel is a beautiful, quaint, quiet yet trendy property. Nice bar/restaurant inside adjacent to lobby. Tons of great shopping and dining within walking distance. Ample onsite parking.

Reviewed on Jun 30, 2026

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Pine Ridge Hotel Deals

TURNING LEAF•Cozy Custom Cabin in the RRG• A true GUEST FAV

TURNING LEAF•Cozy Custom Cabin in the RRG• A true GUEST FAV

Pine Ridge KY
10/10 Exceptional! (139 reviews)
"The communication by/with the host was excellent. The unit was very clean. Convenient location for access to Natural Bridge State Park."

Reviewed on Jun 24, 2026

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TURNING LEAF•Cozy Custom Cabin in the RRG• A true GUEST FAV
Secluded Cliffside Cabin Near Red River Gorge

Secluded Cliffside Cabin Near Red River Gorge

Pine Ridge KY
9.4/10 Exceptional! (337 reviews)
"Large cabin in beautiful setting. We really enjoyed our visit!"

Reviewed on Jun 10, 2026

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Secluded Cliffside Cabin Near Red River Gorge
• KNOTTY PINE•Cozy Cabin in RRG • Hot Tub • Fireplace • Pet Friendly

• KNOTTY PINE•Cozy Cabin in RRG • Hot Tub • Fireplace • Pet Friendly

Pine Ridge KY
9.8/10 Exceptional! (33 reviews)
"Such a lovely cabin in a really quiet and convenient location! The hosts were incredibly responsive, gave lovely local recommendations, and stocked the cabin with plenty of towels and amenities for us to use during our travel. The hot tub was perfect. Would love to stay here again whenever we come ..."

Reviewed on Jun 30, 2026

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• KNOTTY PINE•Cozy Cabin in RRG • Hot Tub • Fireplace • Pet Friendly
See all 868 properties in Pine Ridge
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 Pine Ridge Vacation Packages

Pine Ridge Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Pine Ridge vacation package cost?
You can pick up a vacation package to this popular destination from $559 on Expedia. However, how much your vacation to Pine Ridge costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Pine Ridge?
You can generally find lower rates and better availability in October, November and December. Explore our cheap Pine Ridge vacation packages and you could get some great off-season discounts.
How many days is enough for Pine Ridge?
The ideal length for your Pine Ridge vacation depends on what you'd like to see and do. Generally, a handful of days to a week will give you enough time to check out all the leading sights and discover some hidden spots along the way.
How to find the best Pine Ridge package deals?
Use Expedia's handy filters to find some fabulous Pine Ridge package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Pine Ridge package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Pine Ridge vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component individually. And you'll still get the flexibility to create a personalized Pine Ridge vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Pine Ridge?
If you have your Pine Ridge vacation dates confirmed, book early to bag some outstanding deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Pine Ridge vacation packages?
Your Pine Ridge trip should be an escape from your busy life, 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. Choose one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.