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Vacation rentals in Chickasha

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chickasha

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

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Top guest favorite
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 favorite
A single-story home with a light-colored exterior and a black front door is situated under a clear blue sky. A concrete pathway leads to the entrance, and a grassy area is visible in front of the house, complemented by a large tree providing shade.
Home in Chickasha
4.84 out of 5 average rating, 145 reviews

The Adventure Home

Relax with the whole family at this peaceful place to stay. Our home is located two blocks from USAO and a seven minute to downtown Chickasha, where you can find the Leg Lamp. It is also a three minute drive to Shannon Springs Park, home of the Festival Lights. The home offers a spacious back yard and out door dinning area. Our kitchen is fully equipped to cook in. About this space. It is a two bedroom that can comfortably sleep 5 with a queen and a twin over full bunk bed. *New* Washer/dryer

Guest favorite
A spa bath is positioned against a wall of windows, offering expansive views of the surrounding countryside. The wooden interior features warm tones, and a pebble-stoned area surrounds the bath. Natural light floods the space, enhancing the serene atmosphere.
Cabin in Davis
4.9 out of 5 average rating, 279 reviews

Bird's Nest Tree House-3.5 miles toTurner Falls!

3.5 miles from Turner Falls, elevated 15 feet above ground, "Bird's Nest" first welcomes you with an enchanting view of the Arbuckle Mountains. Then surrounds you with all the custom-built details for a fine getaway, including a pebble stoned walk-in shower and a seperate spa bath. The 70 acres of pristine beauty of nature, shared only with three more cabins, is a destination itself many guests commented:)There is plenty of room for everyone to explore! ~No children allowed due to elevation~

Top guest favorite
Cabin in Blanchard
4.97 out of 5 average rating, 34 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 favorite
A bright living area features light blue walls and hardwood flooring. A comfortable armchair and a small ottoman provide seating options. An entertainment unit displays a large television, and wall art adds color. A lamp stands next to the chair, providing additional light.
Guesthouse in Newcastle
4.94 out of 5 average rating, 174 reviews

Modern, Clean, Cute Private Apartment close to OU!

Guests will love staying at this entire above-home apartment that features tons of amenities to make their stay memorable. This place features a private entrance, coffee, snacks, beverages, Fast Wifi, & free parking! 15 minutes to OU & Riverwind Casino! This place also has a private, covered pavilion that is great for hanging out and cooking on our outdoor grill. Outdoor area may be shared. Our beautiful swing set located in the back yard is perfect for photoshoots or enjoying the weather.

Top guest favorite
The exterior of a single-story home features a covered front porch with a small set of chairs. Two large windows with black shutters are visible on either side of the entrance, flanked by neatly landscaped flower beds and a grassy lawn.
Home in Chickasha
4.89 out of 5 average rating, 54 reviews

Cute Place/Quiet Neighborhood

Enjoy a peaceful stay at our cute-cozy and centrally-located place. There are 3 bedrooms in the home with one bathroom, a small, well equipped kitchen with ice maker in the fridge, cozy living room, TV trays for your dining enjoyment or a small eating area. Enjoy the convenience of the laundry room with a washer and dryer. The fenced in back yard is great for kids, pets, or just hanging out for some outdoor air. This quiet neighborhood is just around the corner from anything you may need.

Top guest favorite
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"

Guest favorite
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 favorite
Home in Chickasha
4.95 out of 5 average rating, 20 reviews

Pet-friendly, fast wifi, large rooms, no clean fee

Welcome to The England House, a charming bungalow in Chickasha where vintage style meets modern comfort. Enjoy high-speed internet (it’s fast, trust us), a workspace, full kitchen, dining room, and comfortable bedrooms with blackout shades. Close to downtown, 5 blocks from USAO, close to the Chickasha Sports Complex and Festival of Light—only 40 minutes to OKC or Norman. Your Stay Chickasha starts here! Easy access for fairgrounds events, shows, and fairs – with space for gear.

Top guest favorite
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, 130 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 favorite
Guesthouse in Hinton
4.97 out of 5 average rating, 206 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 favorite
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, 165 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.

Popular amenities for Chickasha vacation rentals

When is the best time to visit Chickasha?

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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 vacation rentals in Chickasha

  • Total vacation rentals

    Explore 50 vacation rentals in Chickasha

  • Nightly prices starting at

    Chickasha vacation rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 1,310 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chickasha vacation 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

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  4. Grady County
  5. Chickasha