A brown horse lying on the ground in a fenced area with trees in the background.

Grady County Vacations & Trips from $519

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Your Grady County Vacation

Travel on your own terms with a Grady County vacation package. Whether you're going for its walking trails, views, nature, or something else entirely, our package deals make travel planning a breeze. A trip to Grady County wouldn't be complete without spending a few days in Chickasha. This city is one of the best places to visit here. When you're ready to stop daydreaming and start doing, Expedia will help turn your Grady County vacation into a reality.

Top destinations in Grady County

A solitary barn in a vast field under a dramatic sky.
FlightsHotels

Chickasha

Chickasha

The Latest Grady County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A hotel entrance with a large sign reading 'WYNDHAM GRAND,' a bull sculpture, and a landscaped area with plants.
    Feb 5 - Feb 8

    Wyndham Grand Oklahoma City Downtown + Flight

    Downtown Oklahoma City
    3 nights
    4.0 star property
    8.0/10 - Very good (3,516 reviews)
    Roundtrip • New York (EWR) - Oklahoma City (OKC)
    EWR - OKC • 1 stop OKC - EWR • 1 stop
    $595
    $519
    per traveler
    found 1 day ago
    Wyndham Grand Oklahoma City Downtown
  • A restaurant with a bar area, multiple tables and chairs, and decorative lighting fixtures.
    Feb 5 - Feb 8

    Sheraton Oklahoma City Downtown Hotel + Flight

    Downtown Oklahoma City
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,505 reviews)
    "Staff was friends, room service for breakfast was great and the Aria Bar/Restaurant was good vibes and great food. Location is great."
    Reviewed November 11, 2026
    Roundtrip • New York (EWR) - Oklahoma City (OKC)
    EWR - OKC • 1 stop OKC - EWR • 1 stop
    $685
    $567
    per traveler
    found 1 day ago
    Sheraton Oklahoma City Downtown Hotel
  • A modern house with a black front door, three windows, and a small patio with plants and a bench.
    Jan 20 - Jan 23

    House at the Refuge - Relax Take in Nature + Flight

    Medicine Park
    3 nights
    2.0 star property
    Roundtrip • Washington (WAS) - Lawton (LAW)
    DCA - LAW • 1 stop LAW - IAD • 1 stop
    $1,253
    $1,089
    per traveler
    found 18 hours ago
    House at the Refuge - Relax Take in Nature
  • A spacious living room with a large sofa, a coffee table, and a bookshelf filled with books and decorative items. There are two large windows with curtains, and a fireplace with a mantel.
    Feb 5 - Feb 8

    Renaissance Waterford Oklahoma City Hotel + Flight

    Central Oklahoma City
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "Great restaurant, clean facilities, clean nice room comfortable bed"
    Reviewed November 11, 2026
    Roundtrip • New York (EWR) - Oklahoma City (OKC)
    EWR - OKC • 1 stop OKC - EWR • 1 stop
    $656
    $576
    per traveler
    found 1 day ago
    Renaissance Waterford Oklahoma City Hotel
  • A spacious lobby with a fireplace, seating areas, and modern lighting fixtures.
    Feb 5 - Feb 8

    Residence Inn by Marriott Oklahoma City Downtown/Bricktown + Flight

    Bricktown
    3 nights
    3.0 star property
    8.6/10 - Excellent (1,000 reviews)
    "Yolanda was great with everything that we needed and helped the stay be very positive. If we need to stay again downtown okc we will because of her great service!"
    Reviewed November 11, 2026
    Roundtrip • New York (EWR) - Oklahoma City (OKC)
    EWR - OKC • 1 stop OKC - EWR • 1 stop
    $696
    $613
    per traveler
    found 1 day ago
    Residence Inn by Marriott Oklahoma City Downtown/Bricktown

Discover the most popular places to visit in Grady County

Grady County Fairgrounds

8.8/10 (34 reviews)
Enjoy an outing to Grady County Fairgrounds during your stay in Chickasha. Stroll along the riverfront or visit the casinos in this family-friendly area.
See properties

Grady County Hotel Deals

A modern kitchen with a central island, two flat-screen TVs, pendant lighting, and a seating area with yellow chairs and a sofa.

Best Western Plus Chickasha Inn

Best Western Plus Chickasha Inn
2.5 star property
0.9 mi from Grady County
9.2 out of 10, Wonderful, (373 reviews)
$111 nightly
The price is $130
Nov 27 - Nov 28
Total with taxes and fees
Best Western Plus Chickasha 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 Grady County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.