Chickasha Vacation Rentals

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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 Chickasha 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 single-story house with a red door, a front porch, and a small garden.

2. 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 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.

3. 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 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.

4. 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 compact kitchen with a central island, built-in dishwasher, and a ceiling fan.

5. 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 residential house with a front porch, a wooden fence, and a well-maintained lawn.

6. 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 living room with a fireplace, a leather sofa, a wooden chair, and a coffee table.

7. 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.
$246 nightly
The price is $285
Nov 15 - Nov 16
Total with taxes and fees
The Good Vibes | Downtown + 50-Ft Leg Lamp
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a stove.

8. 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.

9. 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.

10. 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.

11. 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.

12. 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.

13. 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.

14. 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 living room with a sofa, two patterned armchairs, a coffee table, and a red vase.

15. 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.
$223 nightly
The price is $232
Nov 11 - Nov 12
Total with taxes and fees
Lions Lair in Blanchard, OK
A wooden cabin-style bedroom with a bed, two bedside lamps, and a fan.

16. 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.
$166 nightly
The price is $172
Nov 11 - Nov 12
Total with taxes and fees
Western cabin in Blanchard, OK
A cabin with a steeply pitched roof, large windows, and a wooden porch.

17. The Pine Needle Cottage at Selah - 2 Bed, 1.5 Bath

The Pine Needle Cottage at Selah - 2 Bed, 1.5 Bath
Norman
10.0 out of 10, Exceptional, (1 review)
"The cute little house was perfect for our girls weekend! The beds were cozy, the esthetic was spot on, and there was plenty of space even though it was tiny. The kitchen was well equipped, the back porch was the perfect place to hang out, and the neighborhood offered so much to see and do!"
United States
Shauna H.
$235 nightly
The price is $246
Nov 11 - Nov 12
Total with taxes and fees
The Pine Needle Cottage at Selah - 2 Bed, 1.5 Bath
A two-story building with a modern design, featuring a large window on the ground floor and a door with a sign that reads 'LAD Nutrition.'

18. Urban Grace at Selah - 2 Bed 2 Bath Luxury Apartment

Urban Grace at Selah - 2 Bed 2 Bath Luxury Apartment
Norman
10.0 out of 10, Exceptional, (1 review)
$272 nightly
The price is $284
Nov 11 - Nov 12
Total with taxes and fees
Urban Grace at Selah - 2 Bed 2 Bath Luxury Apartment
A wooden cabin with a porch, a barbecue grill, and a welcome sign.

19. Italian cabin in Blanchard, OK

Italian cabin in Blanchard, OK
Blanchard
$129 nightly
The price is $134
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.

20. Bear Cabin

Bear Cabin
Blanchard
$129 nightly
The price is $134
Nov 15 - Nov 16
Total with taxes and fees
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.
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Top Chickasha 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

Find out more about Chickasha

Everything you need to know about Chickasha vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chickasha vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chickasha vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chickasha vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chickasha. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chickasha in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $61 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chickasha rentals

At Expedia, we put the best Chickasha vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chickasha rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chickasha vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chickasha. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Are there vacation rentals in Chickasha?

Yes, we offer vacation rentals in Chickasha close to Grady County Fairgrounds, or you can select a 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's the top vacation rental in Chickasha?

Drover House | USAO | Private Pool | King Bed | WD: Visitors give good reviews to this Chickasha vacation home rental, which offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Chickasha are The Rock & Roll | Downtown + 50-Ft Leg Lamp and Ralphie’s House “A Major Award” near Leg Lamp!.

How many vacation rentals are there in Chickasha?

With 13 Expedia vacation rentals, you're sure 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 Chickasaw Pointe Golf Course.

What’s a vacation rental in Chickasha like?

A vacation rental is a private property you can book for several days or longer in Chickasha. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for families.

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