Vacation Rentals in Grady County

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Top cities in Grady County

A solitary barn in a vast field under a dramatic sky.
Vacation Rentals

Chickasha

Chickasha

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Grady County vacation rentals

A gazebo with a white frame and a roof, surrounded by a grassy area and a fence.

1. King Bed | Non-Smoking

King Bed | Non-Smoking
Chickasha OK
10.0 out of 10, Exceptional, (93 reviews)
"Laundromat on-site turned out to be super convenient when I ran low on clothes! Nice not to have to leave the property for that kind of thing either."
United States
Anonymous traveler
$53 nightly
The price is $61
Dec 1 - Dec 2
Total with taxes and fees
King Bed | Non-Smoking
A wooden cabin-style bedroom with a bed, two bedside lamps, and a fan.

2. Western cabin in Blanchard, OK

Western cabin in Blanchard, OK
Blanchard
10.0 out of 10, Exceptional, (1 review)
"Good location. Very nice hosts"
United States
Brandon M.
$162 nightly
The price is $168
Nov 11 - Nov 12
Total with taxes and fees
Western cabin in Blanchard, OK
A wooden cabin with a porch, a barbecue grill, and a welcome sign.

3. Italian cabin in Blanchard, OK

Italian cabin in Blanchard, OK
Blanchard
$126 nightly
The price is $131
Nov 11 - Nov 12
Total with taxes and fees
Italian cabin in Blanchard, OK
A wooden structure with a porch, a welcome sign, and a small table with a yellow flower arrangement.

4. Bear Cabin

Bear Cabin
Blanchard
$126 nightly
The price is $131
Nov 15 - Nov 16
Total with taxes and fees
Bear Cabin
A bathroom with a bathtub, a shower curtain, and marble-patterned tiles.

5. Lions Lair in Blanchard, OK

Lions Lair in Blanchard, OK
Blanchard
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay at Lion’s Lair during OU Family Weekend! My parents were able to join us, and our son stayed with us for the weekend, making it extra special. The house was clean, comfortable, and just a short drive from Norman. We loved being in a quiet, peaceful area while still being close enough to enjoy everything our son wanted to do over the weekend. Communication with the host was excellent from booking to check-in, and we had everything we needed throughout our stay. With our...
United States
Jessica L.
$217 nightly
The price is $226
Nov 11 - Nov 12
Total with taxes and fees
Lions Lair in Blanchard, OK
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a stove.

6. Chickasha ChristmasTown - Family Holiday Retreat

Chickasha ChristmasTown - Family Holiday Retreat
Chickasha
$343 nightly
The price is $402
Nov 11 - Nov 12
Total with taxes and fees
Chickasha ChristmasTown - Family Holiday Retreat
A single-story house with a red door, a front porch, and a small garden.

7. Ralphie’s House “A Major Award” near Leg Lamp!

Ralphie’s House “A Major Award” near Leg Lamp!
Chickasha
10.0 out of 10, Exceptional, (10 reviews)
"The upstairs made a great hangout for the teenage girls in our party. We enjoyed our time together as a family there! "
United States
Cynthia J.
$439 nightly
The price is $509
Nov 11 - Nov 12
Total with taxes and fees
Ralphie’s House “A Major Award” near Leg Lamp!
A residential house with a front porch, a wooden fence, and a well-maintained lawn.

8. The Charm | Dog Friendly | Downtown | Fiber WiFi

The Charm | Dog Friendly | Downtown | Fiber WiFi
Chickasha
10.0 out of 10, Exceptional, (11 reviews)
"I stayed in this location for a work stay and it was very nice. Cute place"
United States
Victoria J.
The Charm | Dog Friendly | Downtown | Fiber WiFi
A modern kitchen with white cabinets, a microwave, and a sink. There is a dining area with a table and chairs, and a neon sign on the wall.

9. The Rock & Roll | Downtown + 50-Ft Leg Lamp

The Rock & Roll | Downtown + 50-Ft Leg Lamp
Chickasha
10.0 out of 10, Exceptional, (5 reviews)
"Great little place. Woukd definitely rent again!"
United States
Jayson m.
$239 nightly
The price is $278
Nov 11 - Nov 12
Total with taxes and fees
The Rock & Roll | Downtown + 50-Ft Leg Lamp
A living room with a fireplace, a leather sofa, a wooden chair, and a coffee table.

10. The Good Vibes | Downtown + 50-Ft Leg Lamp

The Good Vibes | Downtown + 50-Ft Leg Lamp
Chickasha
9.8 out of 10, Exceptional, (15 reviews)
"Very cute VRBO to stay in!"
United States
Donette S.
$248 nightly
The price is $288
Nov 15 - Nov 16
Total with taxes and fees
The Good Vibes | Downtown + 50-Ft Leg Lamp
A compact kitchen with a central island, built-in dishwasher, and a ceiling fan.

11. 3-bedroom 2-bathrooms house in peaceful Chickasha / Downtown area

3-bedroom 2-bathrooms house in peaceful Chickasha / Downtown area
Chickasha
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and location worked great for us. "
United States
BJ R.
$312 nightly
The price is $340
Nov 12 - Nov 13
Total with taxes and fees
3-bedroom 2-bathrooms house in peaceful Chickasha / Downtown area
A kitchen with white cabinetry, a built-in microwave, a stove, a dishwasher, and a refrigerator. There is a window with blinds, a sink, and a countertop with various items.

12. Drover House | USAO | Private Pool | King Bed | WD

Drover House | USAO | Private Pool | King Bed | WD
Chickasha
10.0 out of 10, Exceptional, (13 reviews)
"Very accommodating hosts. Enjoyed the stay."
United States
Larry K.
$363 nightly
The price is $423
Nov 15 - Nov 16
Total with taxes and fees
Drover House | USAO | Private Pool | King Bed | WD
A single-story house with a red door, a front porch, and a small garden.

13. The Pinewood House | Near USAO + Close to Downtown

The Pinewood House | Near USAO + Close to Downtown
Chickasha
$321 nightly
The price is $373
Nov 11 - Nov 12
Total with taxes and fees
The Pinewood House | Near USAO + Close to Downtown
A kitchen with a large island, a coffee machine, and a window with blinds.

14. 1 King Bed & 1 Queen Bed

1 King Bed & 1 Queen Bed
Chickasha OK
10.0 out of 10, Exceptional, (87 reviews)
"Always enjoyed coming back to such clean rooms after long days out exploring."
United States
Anonymous traveler
$57 nightly
The price is $65
Dec 1 - Dec 2
Total with taxes and fees
1 King Bed & 1 Queen Bed
A reception area with a clock, a metal rack, and a television displaying multiple screens.

15. 2 Full Bed | Non-Smoking

2 Full Bed | Non-Smoking
Chickasha OK
10.0 out of 10, Exceptional, (60 reviews)
"Tried using the fitness center daily, decent equipment available allowed me to stick with my routine even while traveling,a definite plus!"
United States
Anonymous traveler
$53 nightly
The price is $62
Dec 1 - Dec 2
Total with taxes and fees
2 Full Bed | Non-Smoking
A kitchen with a large island, a coffee maker, and a red container of Folgers coffee.

16. 1 King Bed & 1 Full Bed

1 King Bed & 1 Full Bed
Chickasha OK
10.0 out of 10, Exceptional, (67 reviews)
"Loved the microwave in our suite. Made it easy to heat up snacks after a long day out exploring Chickasha."
United States
Anonymous traveler
$55 nightly
The price is $64
Dec 1 - Dec 2
Total with taxes and fees
1 King Bed & 1 Full Bed
A hotel lobby with a reception desk, a coffee machine, a framed picture on the wall, and a window with blinds.

17. 3 Full Bed | Non-Smoking

3 Full Bed | Non-Smoking
Chickasha OK
10.0 out of 10, Exceptional, (88 reviews)
"Would book again without hesitation. The room had everything we needed like a fridge and microwave for snacks. Free parking right outside made it easy to unload our bags. Staff were friendly, always ready to help when we had questions about the area."
United States
Anonymous traveler
$60 nightly
The price is $70
Dec 1 - Dec 2
Total with taxes and fees
3 Full Bed | Non-Smoking
A reception area with a clock, a metal rack, and a television displaying multiple screens.

18. 1 King Bed & 2 Full Bed

1 King Bed & 2 Full Bed
Chickasha OK
10.0 out of 10, Exceptional, (55 reviews)
"Parking right outside made unloading simple after a long drive. The connection quality was decent so I could do some work without hassle while there. Having that flexibility was key for me since I needed to balance travel with my tasks while staying here."
United States
Anonymous traveler
$60 nightly
The price is $70
Dec 1 - Dec 2
Total with taxes and fees
1 King Bed & 2 Full Bed
A hotel room with a bed, a desk, a chair, a television, a window with blinds, and a heater.

19. 1 FULL BED | NON-SMOKING, KITCHEN

1 FULL BED | NON-SMOKING, KITCHEN
Oklahoma City OK
9.4 out of 10, Exceptional, (23 reviews)
"Love this place"
United States
Anonymous traveler
$47 nightly
The price is $55
Nov 15 - Nov 16
Total with taxes and fees
1 FULL BED | NON-SMOKING, KITCHEN
A compact kitchen with white cabinets, a stainless steel refrigerator, and a stove.

20. Campus Corner Cabana

Campus Corner Cabana
Norman
10.0 out of 10, Exceptional, (24 reviews)
"Perfect location on Campus Corner. Very convenient for shopping and dining as well as activities on campus."
United States
Jennifer M.
$139 nightly
The price is $139
Nov 11 - Nov 12
Total with taxes and fees
Campus Corner Cabana
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.
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Find vacation rentals that suit your style

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Top Grady County Hotel Reviews

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

Best Western Plus Chickasha Inn
Chickasha

10/10 Excellent

The room was ready and clean, breakfast was delicious staff was very helpful and friendly. The lobby was decorated so cut for Halloween !!!! Plenty of parking space. We would stay there again!!
United States
Debbie
Reviewed October 30, 2026
Best Western Plus Chickasha Inn

Frequently Asked Questions

How many vacation rentals are available in Grady County?

Expedia has plenty of vacation rentals to choose from in and around Grady County, so you’re guaranteed to find the right one for you.


How much is a vacation rental in Grady County?

The selection of Grady County vacation rentals we have selected for you start as low as $59 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Grady County?

Vacation rentals in Grady County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Grady County vacation rentals to suit everyone.


Why should I choose a vacation rental in Grady County?

Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Grady County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.


How do I find the best deal on a vacation rental in Grady County?

Find vacation rentals in Grady County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Grady County.


What amenities are available in a vacation rental in Grady County?

The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Grady County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Grady County?

Everytime is a great time to head to Grady County! Staying in a Grady County vacation rentals you will always find lots going on to keep you entertained.


Why book a vacation rental with Expedia?

Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Grady County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Grady County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Grady County, you can save even more.


Can I cancel my vacation rental through Expedia?

Yes, you can cancel or change your Grady County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.