A wooden gazebo surrounded by dense forest and a large tree with exposed roots.
Photo by Theresa Greene
Open Photo by Theresa Greene

Grayson County Vacations & Trips from $461

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Your Grayson County Vacation

Choose one of our vacation packages to Grayson County and wander wherever your adventurous soul leads you. Walking trails and culture are just a couple of the things you can look forward to in this vibrant destination. A trip to Grayson County wouldn't be complete without spending a day or two in Leitchfield. This city is one of the top places to visit here. Stop dreaming and start packing, because your Grayson County vacation is only clicks away with Expedia.

Top destinations in Grayson County

A valley with a river, surrounded by autumn-colored trees and hills.
FlightsHotels

Leitchfield

Leitchfield

The Latest Grayson County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A gym with cardio machines, weight equipment, and a TV screen.
    Jan 22 - Jan 25

    Hyatt Regency Louisville + Flight

    Downtown Louisville
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,001 reviews)
    "Parking was a breeze! It is right across from the convention center with a connecting walkway! The restaurant was delicious and having the Starbucks available in the morning for coffee really made the trip perfect."
    Reviewed November 11, 2026
    Roundtrip • Chicago (ORD) - Louisville (SDF)
    ORD - SDF • Nonstop SDF - ORD • Nonstop
    $645
    $461
    per traveler
    found 15 hours ago
    Hyatt Regency Louisville
  • An indoor dining area with tables set for guests, surrounded by potted plants and hanging lights.
    Jan 15 - Jan 18

    Hotel Distil, Autograph Collection + Flight

    Downtown Louisville
    3 nights
    4.0 star property
    9.6/10 - Exceptional (520 reviews)
    "Very luxurious hotel in a great location for great restaurants and some shopping. Close to some Louisville attractions like the Slugger museum, Angel’s Envy and Old Forester distilleries. The Repeal restaurant inside the hotel was truly a perfect experience!"
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Louisville (SDF)
    BOS - SDF • 1 stop SDF - BOS • 1 stop
    $977
    $820
    per traveler
    found 14 hours ago
    Hotel Distil, Autograph Collection
  • A Marriott hotel entrance with a modern glass canopy, a brick facade, and a clear sky.
    Dec 24 - Dec 28

    Marriott Louisville East + Flight

    Jeffersontown
    4 nights
    4.0 star property
    9.0/10 - Wonderful (1,000 reviews)
    "It was a great stay for the gaming convention. Everything thing was great."
    Reviewed November 8, 2026
    Roundtrip • Fort Lauderdale (FLL) - Louisville (SDF)
    FLL - SDF • 1 stop SDF - FLL • 1 stop
    $614
    $520
    per traveler
    found 1 day ago
    Marriott Louisville East
  • A modern interior with a fireplace, bookshelves, a green sofa, and leather chairs.
    Jan 15 - Jan 18

    The Grady + Flight

    Downtown Louisville
    3 nights
    4.0 star property
    9.4/10 - Exceptional (1,011 reviews)
    "The design is amazing!"
    Reviewed November 9, 2026
    Roundtrip • Boston (BOS) - Louisville (SDF)
    BOS - SDF • 1 stop SDF - BOS • 1 stop
    $808
    $692
    per traveler
    found 14 hours ago
    The Grady
  • A spacious lobby with a high ceiling, a central chandelier, and seating areas with tables and chairs.
    Dec 31 - Jan 2

    Omni Louisville Hotel + Flight

    Downtown Louisville
    2 nights
    4.0 star property
    9.4/10 - Exceptional (2,232 reviews)
    Roundtrip • Chicago (CHI) - Louisville (SDF)
    ORD - SDF • Nonstop SDF - ORD • Nonstop
    $618
    $529
    per traveler
    found 8 hours ago
    Omni Louisville Hotel

Discover the most popular places to visit in Grayson County

Rough River Dam State Resort Park

9.6/10 (40 reviews)
You can take time to visit Rough River Dam State Resort Park during your travels to Falls of Rough. Stroll along the lakeside or experience the area's theater scene.
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Grayson County Hotel Deals

A restaurant with round tables and chairs, a coffee station, and framed pictures on the walls.

Hatfield Inn

Hatfield Inn
2.5 star property
0.8 mi from Grayson County
8.6 out of 10, Excellent, (383 reviews)
"I was disappointed because the A/C was loud and making a noise. There was also a dehumidifier in the room making noises. We did turn off the A!C off, but then could hear the neighbors. The breakfast was sub~par, there was very little to choose from. Cereal, muffins, fruit and yogurt, With the higher rating this hotel had, we at least, expected eggs"
$132 nightly
The price is $147
Nov 13 - Nov 14
Total with taxes and fees
Hatfield Inn
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.
See all properties in Grayson County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.