Chickasha is a small city in Grady County, Oklahoma, with droves of things to do. Located just south of the Oklahoma City metropolitan area, there are several buildings in the city that are on the National Register of Historic Places, such as Griffin House and New Hope Baptist Church. Chickasha hosts the notable Festival of Light, which takes place during the winter and features millions of lights on trees, romantic carriage rides and Christmas spirit in every corner. There’s also the Arts Festival, sporting events and other entertainment events for you to check out. If you’re planning to go to these events, keep reading to discover the top Airbnb vacation rentals in and near Chickasha, Oklahoma.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 15, 2025.
1. The Charm (from USD 245)
This cozy rental house in Chickasha is an ideal location for short- and long-term stays alike. There’s a designated work desk here, which means you can merge your working and living environment smoothly. During your breaks, take advantage of the books and reading materials left by the host. You can also nap in the bedroom with room-darkening shades.
The shared backyard boasts a barbecue for those who enjoy grilled delicacies. Although the accommodation is within walking distance of the historic downtown area, it also has free parking for your convenience.
Chickasha, Oklahoma, United States
32.82 km (20.4 mi) from Williamson farmsSuperhost
Accommodates: 6
Top guest reviews
Host:
quick and friendly responses from the hostthe hosts are very responsivethe hosts and place were wonderfulbest hosts in the whole worldvery cozy the homeowners are very attentive and make you feel so warm and welcomedLocation:
great location for playing at chickasha sports complexamazing people with an amazing location a must tryextremely clean unit close to everything that chickasha has to offerCleanliness:
house is very clean and comfortablethe house was adorable very clean and cozyplace was beautifully appointed and sparkling clean quiet and serenegreat place quiet and cleanimmaculately clean adorably decorated and shane & maggie were extremely easy to communicate withRead more reviewsAmenities & Room:
such a comfortable place and many thoughtful touches
2. Apartment in the heart of the Paseo Arts District (from USD 462)
Very conveniently located in the Paseo Arts District and near numerous bars, restaurants, galleries, and shops, this artistic Airbnb vacation rental in Oklahoma City has eclectic decor and may accommodate up to five guests. The house comes with two cozy bedrooms, one full bathroom, a fully stocked kitchen, and a splendid sunroom to enjoy some time off.
A laptop-friendly workspace is also provided, thus making the place ideal for business travelers. Choose this place to enjoy the loveliest and most walkable neighborhood of Oklahoma City.
Oklahoma City, Oklahoma, United States
31.67 km (19.7 mi) from Williamson farmsAccommodates: 4
Top guest reviews
Host:
host was easy to communicate withshe was very accommodating and responsivegreat house great hostbeautiful house and excellent hoststhe host was very responsive and provided a guidebook for things to do in the cityLocation:
wonderful location and cute comfortable housegreat location to a great neighborhoodawesome location and very good valuegreat place wonderful locationgreat location charming artist enclaveCleanliness:
counters obviously hadn’t been cleangreat space clean and usualvery clean with comfortable beds and an overall welcoming atmospheregreat place clean comfortable and convenientdenise’s place was very comfortable clean and privateRead more reviewsAmenities & Room:
the king sized bed was very comfortable as were the other furnishingsbed was comfortable and clean and coffee to start our dayplenty space and very comfortableclean ac was on when we arrived parking and a full kitchen
3. Private room and bathroom (from USD 31)
The spacious house is conveniently located just 25 minutes from the airport and a short drive away from Norman. The room on offer has a tasteful interior with oak dormer windows and a lovely new carpet while it enjoys its own private bathroom. Except for being a child-friendly apartment, the indoor fireplace and the free parking will make your stay really comfortable. If you are a romantic soul, you will simply enjoy gazing at the stars in the nights or the dazzling sunsets. The property is located in Tuttle, rural Oklahoma, thus don’t expect much public transportation.
Tuttle, Oklahoma, United States
4.58 km (2.9 mi) from Williamson farmsAccommodates: 7
Top guest reviews
Host:
david was a great host without a doubtthey are perfect hosts and very accommodatingdavid was very friendly and enjoyed hanging out with my group of friendsdavid and jennifer are great hostsdavid and jennifer were very nice hosts and gave recommendations on activities and restaurantsLocation:
close to i44 but definitely countrythe neighborhood is quiet and hugei would recommend this location to anyone looking for a family friendly and quiet placeCleanliness:
very clean quietthe room was very spacious clean and comfortablethe room was amazing clean and very bigthe place was spacious clean and very comfortablethe room was spacious clean and exactly what we neededRead more reviewsAmenities & Room:
the beds were super comfy toothe private bath was great and the a/c was greatbeautiful home and the room was huge with it's own privet bathroom
4. Earthy two-room suite (from USD 60)
You will find this artistically decorated house in Norman, very close to a number of fine restaurants and shopping centres. Although there is only one room for rent, the space is large enough to sleep a maximum of six guests (including children), while they have access to the well-equipped kitchen, the laundry room or the dining/living room. The ambience that fills the place is due to the vaulted ceilings, in case you wonder why it feels so great to be here. This is a perfect place to stay if you are visiting the Medieval Fair or Norman Music Fest.
Norman, Oklahoma, United States
16.47 km (10.3 mi) from Williamson farmsTop guest reviews
Host:
friendly hostshe is such a good hostrobin was a great hostsuper nice host generous & friendlyrobin is an amazing kind hostLocation:
this is a great locationconveniently located parked in driveway pretty home spacious area for gueststhe place is spacious and in a great neighborhoodrobin’s place is very charming and cozyher place is comfortable secure kid friendly easy to find and very accommodatingRead more reviewsCleanliness:
clean functional and comfortablethe place was clean and cozyvery clean very comfortable would stay here againrobin was very nice and made sure everything was clean and prepared for ussuper clean with all the amenities
5. Nautical apartment (from USD 80)
This is the perfect place to stay if for any reason you are visiting Oklahoma University, which is actually only a 10-minute drive away. The spacious studio apartment can easily sleep two guests, who have at their disposal a bathroom and a basic kitchenette. Take advantage of the cute balcony to enjoy a drink or a quiet evening reading a book.
Although resting in a quiet neighborhood, the property enjoys close proximity to tons of shops and eating venues, while the Riverwind Casino and Southwind Hills are literally a three-minute drive away.
Norman, Oklahoma, United States
15.84 km (9.9 mi) from Williamson farmsTop guest reviews
Host:
the hosts are amazing peopleeverything was provided promptly and the owners made sure we were securei was welcomed and always checked on by the ownersthe hosts were very nice friendly and helpfuldoug was very hospitable and friendly and we definitely enjoyed our stayLocation:
the location was great near ou just a 10-15 minute drive awayquiet neighborhood conveniently located and i will definitely be backit is a great central location for anything in moore and normangreat place to stay for a weekend in norman location is convenient to the ou campusgreat place to stay if your going to explore norman for the weekendCleanliness:
the condo towels and bed sheets were very cleanthis place is so cute and cleanthis place was great for a quick night very clean easy to check in and good locationRead more reviewsAmenities & Room:
the air mattress was surprisingly comfortable and spaciousthe nautical style apartment was a really cool themeit was very comfortable and had a nice kitchen area
6. Cozy apartment with a balcony (from USD 30)
Perfect for small groups but also for solo adventurers, this chilled-out flat will instantly make you feel at home. The house comes with a large room consisting of a living/dining area plus an office, a bathroom, a well-equipped kitchen and a lovely balcony with chairs. The super comfy bed and the extremely accommodating host are definitely the highlights of your stay. Besides enjoying easy access to several shops, restaurants and bars, this listing is also a block away from Natural Grocers.
18.55 km (11.6 mi) from Williamson farms
7. Bonus private room (from USD 40)
Perfect for couples or solo travellers who want to crash in for a night or two, guests may enjoy the whole second floor of this house, where a room, bathroom and living room are all private. However, by all means, guests can have access to the kitchen and the laundry area, while they are provided with all home essentials and a satellite television as well. The property might be nestled in a rural area, yet the airport is only 15 minutes away and similarly, Oklahoma City some 20 minutes drive away.
11.25 km (7.0 mi) from Williamson farms
8. Guest room with a private bathroom (from USD 20)
Ideal for independent travelers or couples, this private room enjoys its own private bathroom, where Egyptian cotton towels will absolutely make the difference. Guests are entitled to use the kitchen with all the basic cooking utensils, and the living room which surprisingly comes with all the latest electronic equipment.
A beautiful duck pond is just around the corner inviting you to take a rest. Guests can easily reach Sooner Mall within 10 minutes, while downtown Oklahoma or Bricktown are just half an hour away.
20.69 km (12.9 mi) from Williamson farms
9. Quirky, spacious cabin (from USD 120)
Relax and forget all your worries or arrange a lovely family reunion in this fascinating 2-story cabin that lies on 31 acres (12.55 hectares) and can easily fit up to 10 guests. If you are into sports, you will love this place, as there are volleyball and basketball courts, as well as a pool (seasonal) and a pond (with canoe possibility) just outdoors.
The area is pretty much secluded, so don’t expect the fastest internet connection; remember. You are here to enjoy the rural landscape. Nevertheless, the most adventurous souls may travel 29 kilometers (18 miles) to Wichita Mountain Wildlife Refuge or the bustling city of Lawton.
72.17 km (44.9 mi) from Williamson farms
10. Farmhouse with great outdoors (from USD 250)
This humble farmhouse is beautifully surrounded by acres of grapevines and is a must-visit place for the wine-lovers. It is large enough to sleep up to nine guests, who will have the chance to try the tasting room or the host’s highly rated restaurant. The rodeo arena will be the highlight of your stay, which you may, of course, enjoy when in action. The house comes with all basic amenities, as well as all cooking utensils to make your own meals, while your host is super friendly and welcoming.
Anadarko, Oklahoma, United States
64.6 km (40.2 mi) from Williamson farmsAccommodates: 12
Top guest reviews
Host:
great little country escape alexis was great hosther staff are always helpful and informativealexis was attentive and her staff was really friendlyalexis was a great hostthe employees from the winery were welcoming & friendlyLocation:
excellent place with delicious wine only a short walk awaya good country location 40 minutes from lawtonloved the sweet house and location could not have asked for morethis is an ideal airbnb for those looking for a relaxing quiet time awaywe really enjoyed being surrounded by quiet and the oklahoma countryside at the houseCleanliness:
it was very spacious and cleanthe house inside was mostly clean and was a comfortable spaceeverything is clean and well maintained but it’s not the ritza very nice spacious house in a quiet secluded area within a winery yardRead more reviewsAmenities & Room:
a great spot to get away from wifi and cell phonesthe beds were super comfyour stay was very nice the house is not fancy but serviceable and comfortablewe also conveniently cooked a few meals easily prepared in the kitchenthe food in the dining room is amazing
11. Spacious three-bedroom home (from USD 150)
A great place for families or groups of friends, this large house comes with three bedrooms, two bathrooms, a well-stocked kitchen (with a Keurig coffee maker), and a living room that actually hosts a piano (for music lovers). It will certainly be a haven for children who can enjoy time outside on the swingset or the playhouse, while the adults relax and unwind on the back patio. Indoors, guests may enjoy the coziness of the fireplace or endless hours with the company of Netflix and Hulu on the smart TV.
Although tucked away in a peaceful neighborhood, the property is only 15 minutes away from the airport and another 20-minute drive to Oklahoma downtown.
Newcastle, Oklahoma, United States
7.79 km (4.9 mi) from Williamson farmsAccommodates: 5
Top guest reviews
Host:
the house was amazing and amy was a fantastic hostamy was super accommodatingamy and her husband are very friendly and helpfulwe could not have asked for better hosts or a better space for our time theregreat neighborhood clean environment and very friendly/professional hosts definitely will returnLocation:
great location close to the highway in a quiet neighborhoodthis is a nice home in a great locationRead more reviewsCleanliness:
everything was clean and modernthe house was clean with comfortable bedsyour house is super beautiful clean and cosytheir home was very clean and inviting and we felt perfectly safe thereshe has a lovely clean home in a safe neighborhood
12. The 17th House (from USD 129)
Explore the character of The 17th House, an absolutely charming home for rent in Chickasha. This accommodation sits on a quiet street but is still near restaurants so that you can get a taste of the local favorites. Free parking is available on location if you need somewhere to leave your vehicle between sightseeing. After culinary adventures, relax by switching on the 42-inch (106.68-centimeter) HDTV with access to several streaming platforms.
The backyard and shared patio are the perfect places to unwind in the sunshine. If you have small kids, they’ll enjoy resting on the grass.
Chickasha, Oklahoma, United States
33.28 km (20.7 mi) from Williamson farmsAccommodates: 8
Top guest reviews
Host:
hosts responded very quickly and were very helpfulgreat host they worked with us when our event was rescheduledgreat place micah and cara were very responsive when i asked a couple questionsmicah and cara were super responsive with all questions during our staygreat stay micah and cara were very accommodating when we decided to add another day to our reservationLocation:
the house is a great location for our event house is beautifulthe house was well supplied in a good location and met all our needsperfect place to stay for games at the sports complexCleanliness:
very nice and clean houseoverall it was a nice place clean and quiet neighborhoodthe home was clean and comfortablevery welcoming house to stay in the home is nicely decorated and clean with reliable amenitiesawesome home friendly hosts clean and comfortableRead more reviewsAmenities & Room:
the only thing that could use improvement will be the kitchen and living room furniturethe bathrooms have been nicely remodeled and are well stocked with toiletriesmade it comfortable and smooth for the whole family
Chickasha: so much to offer
This lovely city and its beautiful surrounding villages have so much to offer to visitors. Be sure to book a place to stay in Chickasha in advance to avoid disappointment.
Frequently asked questions about the top Airbnb vacation rentals in and near Chickasha, Oklahoma
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