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Holiday houses in Chickasha

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chickasha

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious living area features soft carpeting and neutral-toned walls. A comfortable sofa is positioned near a wooden TV stand, which holds a Smart Roku TV. Two upholstered chairs are placed beside a floor lamp, with natural light streaming through the adjacent windows.
Cottage in Tuttle
4.97 out of 5 average rating, 321 reviews

⭐️Backyard Bungalow⭐️Work Travel Friendly

Our Backyard Bungalow is cozy with country charm. Enjoy a peaceful morning on the porch with a hot cup of coffee. Located only 13 miles from Will Rogers Airport and the FAA Academy, this bungalow will give you the comfort of home as you're traveling. The bungalow is located adjacent to the owners home within a quiet neighborhood and just 20 miles from both Oklahoma City and Norman. Internet access will be provided, along with ample space for work-related needs. We look forward to your stay!

Guest favourite
An A-Frame cabin is showcased, featuring a light green exterior and a triangular roof. A spacious wooden deck offers access to the entrance, surrounded by a grassy area and bare trees. The clear sky enhances the peaceful setting of the property.
Cabin in Noble
4.97 out of 5 average rating, 169 reviews

Secluded A-Frame Cabin near Lake Thunderbird & OU

Relax & unwind, this beautiful A-Frame cabin is nestled on 2.5 private acres of peace and quiet. Escape the city life in this immaculate cabin featuring a modern kitchenette with new furnishings. The spiral stairs lead to a comfortably sized loft and sleeping area. A short drive away you can experience local wineries, attractions, and the ever popular Lake Thunderbird State Park. Once back home it is time to enjoy the spacious deck with Chiminea along with spectacular views of the landscape.

Superhost
Home in Chickasha
4.94 out of 5 average rating, 63 reviews

The Charm Chickasha | Fiber | W/D | Dog Friendly

The Charm is a large 850 sq feet 1 bedroom, 1 bath home located just 6 blocks from Historic Downtown Chickasha and dog friendly. The property was fully remodeled down to the studs and is loaded with a fully stocked kitchen and laundry plus all the amenities you need for a relaxing and comfortable stay. Located near Downtown Chickasha close to the Fairgrounds and sports complex with easy access to anything in Chickasha! 2 mins → Historic Downtown Chickasha + 50 Ft Leg Lamp! 35 mins → Will Rogers

Top Guest favourite
A living area features a dark leather couch, positioned on a striped black and white rug. Natural light filters through a window beside a sliding barn door. Wooden walls and ceiling create a warm ambiance within this welcoming space.
Barn in Hinton
5 out of 5 average rating, 52 reviews

Happy Trails Barndominium

Unique barndominium minutes from I-40. This quiet space has wifi and TV in the living area. The master bedroom has a queen bed as well as a desk and TV. The smaller bedroom has a full-size bed. There is one spacious bathroom with a tile shower, washer and dryer. The kitchen has a full-size refrigerator, gas stove, microwave and dishwasher. The standout feature of this property is a 40X40 enclosed barn, perfect for multi-vehicles and trailer parking as well as hunters. Door to barn is 9X10.

Top Guest favourite
Cabin in Blanchard
4.97 out of 5 average rating, 33 reviews

Secluded Log Cabin - Cozy Fire Pit - NEW hot tub

Nestled in the serene woods, our charming log cabin offers the perfect getaway for nature lovers and those seeking tranquility. This cozy cabin backs right up to a peaceful pond, providing picturesque views. Inside, you’ll find rustic charm combined with modern comforts, creating a warm and inviting atmosphere. Spend your days exploring the surrounding trails, fishing in the pond, or simply relaxing on the porch, soaking in the beauty of the great outdoors. Your unforgettable escape awaits!

Top Guest favourite
A charming entrance to the cottage is framed by wooden steps leading up to a covered porch. Flower boxes adorn the windows, adding greenery. A grill sits to the side, surrounded by natural landscaping, creating a serene outdoor environment.
Tiny home in Wanette
4.98 out of 5 average rating, 794 reviews

Sage Guest Cottage! Your Own Very Private HotTub!

Sage Cottage is located in the beautiful Pottawatomie County in our own Oaklore Forest. The cottage sleeps two on our queen size bed, Has a mini-kitchen and 3-piece bathroom with stand-up shower. The kitchen is equipped with a small bar sink, double hot plate, toaster, microwave, coffee pot, kuerig, toaster oven, small fridge and cooking essentials. There is a bistro table, picnic table, grill & breakfast table inside! Free Wi-Fi, Hot tub open all year, robes, see "other things to note"

Superhost
Home in Chickasha
5 out of 5 average rating, 4 reviews

Spacious MCM, Hot Tub/Sauna/Cold Plunge/Weights

This midcentury modern charmer has so much space for you, your belongings, friends and family! We are located right off Missouri Ave in Chickasha, near the Festival of Light, USAO & fairgrounds. Original pink & blue tiles in the bathrooms are so unique and the bedrooms have ample space. Comfortable furniture with fast wifi, a game/card table and dining table. The kitchen features a Frigidaire Flair stove! Read our guest access section: we have a hot tub, sauna, weight room & cold plunge!

Guest favourite
A spacious living area showcases a comfortable brown sofa with decorative cushions, paired with a rustic coffee table on a patterned rug. The open kitchen features dark cabinetry and stainless steel appliances, with natural light brightening the space through a nearby window.
Farm stay in Wanette
4.97 out of 5 average rating, 121 reviews

Exotic Animal Hotel

Come stay in your very own unique safari room! Come stay the night with over 100 exotic animals from around the world! We are an exotic animal encounter experience! Your windows from your room are connected to the ringtail lemur and ruffed lemur enclosures! There is also a fire pit, playground, and a ton of hiking! You can even see a lot of the animals from outside your Airbnb! This is a very family oriented environment! You are encouraged to just relax and spend time with your family!

Top Guest favourite
A cozy sleeping area features a spacious bed with decorative pillows and a green comforter. Wall art depicting an Italian scene complements the calming atmosphere. Nightstands are positioned on either side, and a mounted television is visible, alongside a small electric fireplace for ambiance.
Cabin in Blanchard
4.95 out of 5 average rating, 128 reviews

Italian Cabin

At Lori’s Country Cabins you can kick back and relax at this unique and peaceful getaway in the country but still close to town. The Italian cabin offers a private porch with seating, charcoal grill and a fire pit right outside your duplex style cabin. Fix a snack or a full meal with a kitchenette. More than two staying, no worries there is a loft with a movable ladder for easy access with a floor mattress. Pets are welcome with a non-refundable pet fee.

Top Guest favourite
Guesthouse in Hinton
4.97 out of 5 average rating, 205 reviews

Hidden Treasure Pool House Near I-40

If you like a little extra in your travels, you're welcome to our 1300 sq. ft. Guest Home on a 17 acre setting just 35 minutes from downtown OKC or 20 minutes from Weatherford OK. Secure location with a gated entry and some quiet scenic country but just a short drive away from the action in OKC. Great place for couples, solo adventurers, business travelers, and a family with children. NO parties or large groups. No more than 6 people on the premises.

Top Guest favourite
A modern shipping container retreat is framed by lush greenery, showcasing a spacious porch with seating and large windows. The exterior is accented by well-maintained landscaping and a gravel driveway leading up to the entrance.
Shipping container in Chickasha
4.99 out of 5 average rating, 163 reviews

Serenity Cottage + hot tub in the country

Relax. Refocus. Write a special moment into your story. Our thoughtfully designed shipping container is where comfort and elegance intertwine. We want your stay to be filled with simple pleasures. No TV but fast WiFi for your devices. Find solace on the porch, sipping coffee with a fresh cinnamon roll. Immerse yourself in relaxation in the hot tub. As evening falls, gather around the fire pit under the starlit sky.

Guest favourite
An open living space features light wood flooring and a modern kitchen with blue cabinetry and stainless steel appliances. A cozy sofa is positioned in front of a coffee table, with a large flat-screen TV mounted on the wall. Natural light fills the area through windows.
Home in Chickasha
5 out of 5 average rating, 23 reviews

Brand New Modern Home! 0.5 miles to Downtown!

New to Airbnb, this modern brand new cottage is ready for your next trip. Great Location! Walk to downtown. Just half a mile to Downtown Chickasha with food and shopping options. Wood floors, granite counter tops, a small fenced backyard and brand new appliances. I am an AirBNB Superhost so you can expect a flawless stay every time. Military Discounts Apply! Pets Welcome! this peaceful and centrally-located place.

Popular amenities for Chickasha holiday rentals

When is the best time to visit Chickasha?

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Avg. price$145 NZD$145 NZD$152 NZD$160 NZD$160 NZD$165 NZD$160 NZD$150 NZD$153 NZD$150 NZD$153 NZD$150 NZD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Chickasha?

    Chickasha has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in hotel rentals in Chickasha?

    Experience the best of Chickasha with our hotel rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Chickasha?

    Four-legged friends are welcome in Chickasha. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Chickasha?

    Yes! Work meets play with ease at over 30 vacation rentals in Chickasha featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do hotel rentals in Chickasha have air conditioning?

    Absolutely! We offer over 10 hotel rentals with air conditioning in Chickasha. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chickasha have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Chickasha. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chickasha have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Chickasha. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chickasha have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Chickasha. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Chickasha

  • Total holiday rentals

    Explore 50 holiday rentals in Chickasha

  • Nightly prices starting at

    Chickasha holiday rentals start at $68 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chickasha holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chickasha rentals

  • 4.7 Average rating

    Chickasha stays receive an average rating of 4.7 out of 5 from guests

  1. Airbnb
  2. United States
  3. Oklahoma
  4. Grady County
  5. Chickasha