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

Chickasha Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chickasha holiday rentals

1. 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 traveller
The price is NZ$135
includes taxes & fees
8 Oct - 9 Oct
3 Full Bed | Non-Smoking

2. 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.
The price is NZ$625
includes taxes & fees
27 Sept - 28 Sept
3-bedroom 2-bathrooms house in peaceful Chickasha / Downtown area

3. 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.
The price is NZ$568
includes taxes & fees
1 Oct - 2 Oct
The Good Vibes | Downtown + 50-Ft Leg Lamp

4. The Cozy | Downtown + 50-Ft Leg Lamp

The Cozy | Downtown + 50-Ft Leg Lamp
Chickasha
9.8 out of 10, Exceptional, (8 reviews)
The price is NZ$476
includes taxes & fees
19 Oct - 20 Oct
The Cozy | Downtown + 50-Ft Leg Lamp

5. 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.
The price is NZ$568
includes taxes & fees
1 Oct - 2 Oct
The Rock & Roll | Downtown + 50-Ft Leg Lamp

6. 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, (9 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.
The price is NZ$803
includes taxes & fees
1 Oct - 2 Oct
Ralphie’s House “A Major Award” near Leg Lamp!

7. The Charm | Downtown + Dog Friendly

The Charm | Downtown + Dog Friendly
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 price is NZ$473
includes taxes & fees
28 Sept - 29 Sept
The Charm | Downtown + Dog Friendly

8. Chickasha ChristmasTown - Family Holiday Retreat

Chickasha ChristmasTown - Family Holiday Retreat
Chickasha
The price is NZ$656
includes taxes & fees
29 Sept - 30 Sept
Chickasha ChristmasTown - Family Holiday Retreat

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

Drover House | USAO | Private Pool | King Bed | WD
Chickasha
10.0 out of 10, Exceptional, (12 reviews)
"Very accommodating hosts. Enjoyed the stay."
United States
Larry K.
The price is NZ$801
includes taxes & fees
28 Sept - 29 Sept
Drover House | USAO | Private Pool | King Bed | WD

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

The Pinewood House | Near USAO + Close to Downtown
Chickasha
The price is NZ$718
includes taxes & fees
27 Sept - 28 Sept
The Pinewood House | Near USAO + Close to Downtown

11. 1 King Bed & 1 Queen Bed

1 King Bed & 1 Queen Bed
Chickasha OK
10.0 out of 10, Exceptional, (85 reviews)
"Always enjoyed coming back to such clean rooms after long days out exploring."
United States
Anonymous traveller
The price is NZ$128
includes taxes & fees
26 Sept - 27 Sept
1 King Bed & 1 Queen Bed

12. King Bed | Non-Smoking

King Bed | Non-Smoking
Chickasha OK
10.0 out of 10, Exceptional, (92 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 traveller
The price is NZ$119
includes taxes & fees
27 Sept - 28 Sept
King Bed | Non-Smoking

13. 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 traveller
The price is NZ$138
includes taxes & fees
29 Sept - 30 Sept
1 King Bed & 2 Full Bed

14. 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 traveller
The price is NZ$123
includes taxes & fees
27 Sept - 28 Sept
1 King Bed & 1 Full Bed

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 traveller
The price is NZ$119
includes taxes & fees
23 Oct - 24 Oct
2 Full Bed | Non-Smoking

16. Secluded Modern Farmhouse on 3 Acres - 4m. from all things Chickasha

Secluded Modern Farmhouse on 3 Acres - 4m. from all things Chickasha
Ninnekah
10.0 out of 10, Exceptional, (1 review)
"It was great. We really enjoyed staying there. There were a lot of spiders in the other building. A bathroom in the other building would have been nice. But overall was a very cute and cozy place. It was very clean and accommodating. We will stay again if we are close again. Thank you. Any problems we had. They sent someone out very quickly to fix it. "
United States
Donita H.
The price is NZ$706
includes taxes & fees
27 Sept - 28 Sept
Secluded Modern Farmhouse on 3 Acres - 4m. from all things Chickasha

17. Western cabin in Blanchard, OK

Western cabin in Blanchard, OK
Blanchard
The price is NZ$317
includes taxes & fees
8 Oct - 9 Oct
Western cabin in Blanchard, OK

18. Lions Lair in Blanchard, OK

Lions Lair in Blanchard, OK
Blanchard
The price is NZ$422
includes taxes & fees
8 Oct - 9 Oct
Lions Lair in Blanchard, OK

19. Italian cabin in Blanchard, OK

Italian cabin in Blanchard, OK
Blanchard
The price is NZ$249
includes taxes & fees
8 Oct - 9 Oct
Italian cabin in Blanchard, OK

20. Bear Cabin

Bear Cabin
Blanchard
The price is NZ$249
includes taxes & fees
8 Oct - 9 Oct
Bear Cabin
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chickasha Hotel Reviews

Find out more about Chickasha

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chickasha holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chickasha. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chickasha. Seeing all the best attractions is bound to make you fall in love with Chickasha. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chickasha short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Frequently asked questions

Are there holiday rentals in Chickasha?

Yes, there are holiday rentals in Chickasha close to Grady County Fairgrounds, or you can select a more secluded option if you're looking for a relaxing stay. Chickasha is known for its baseball games and university setting. Make sure you have time to check out the riverfront and gardens during your trip.

What are some of the best holiday rentals that Chickasha has to offer?

The Rock & Roll | Downtown + 50-Ft Leg Lamp: This highly rated holiday home rental in Chickasha offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of books. Some other top choices in Chickasha are Drover House | USAO | Private Pool | King Bed | WD and 3-bedroom 2-bathrooms house in peaceful Chickasha / Downtown area.

How many holiday rentals are there in Chickasha?

With 13 Expedia holiday rentals, you're guaranteed to find just the right place for your Chickasha stay.

What’s there to see and do in Chickasha?

Family-friendly attractions include The Maize at Reding Farm and Muscle Car Ranch, whereas Chickasha Sports Complex and 12th Street Park are a couple of great spots to enjoy the outdoors. Other places in town to visit include Grady County Fairgrounds and Grady County Historical Society Museum.

What’s a holiday rental in Chickasha like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chickasha. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for family gatherings.