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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 red barn-style building is set within a green lawn, offering ample outdoor space. The structure features multiple windows and a large roll-up door. A military vehicle is parked alongside, with trees lining the background, creating a serene setting.
Farm stay in McLoud
4.96 out of 5 average rating, 367 reviews

Entire Barndominium located on 5 acres!

Enjoy a peaceful setting on 5 acres with a stocked fishing pond. 1 bedroom(additional queen murphy bed)/1.5 bath with washer and dryer for extended stays. Close to local ballfields if traveling with a team. Fiber optic wifi, tv's, full kitchen, king bed, fully furnished, & newly added tornado shelter. Plug ins available to hookup your EV charger. This property of ours is under constant improvement. We are happy to share a little slice of our heaven with others! Pets welcomed with applicable fee.

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!

Top guest favorite
The exterior of the barndominium is showcased with a metal and wood façade. A spacious covered porch is present, supported by two sturdy posts. Green grass surrounds the building, and a barbecue grill is visible to one side.
Home in Norman
5 out of 5 average rating, 85 reviews

Peaceful Luxury Barndo w/ Stunning Views

Luxury Barndominium located conveniently close to University of Oklahoma - Riverwind Casino & Southwind Hills Wedding Venue. Relax & unwind while taking in views of Downtown OKC & OU Stadium from our secluded hilltop w/ outdoor living space to Dine/Grill/sit around the fire. 2 Bedroom/1 Bath Home sleeps up to 6 people, making this the perfect getaway location for whatever brings you to the Norman area. High-end build quality & thoughtfulness will truly make this feel like a Home away from Home.

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

Top guest favorite
Cabin in Blanchard
4.97 out of 5 average rating, 35 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
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.

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

Pet Friendly, 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 favorite
Home in Chickasha
5 out of 5 average rating, 45 reviews

Rock & Roll Chickasha | Fiber | TV | W / D | Parking

The Rock & Roll is a 2 bed, 1 bath home located just 6 blocks from historic downtown Chickasha. The property was fully remodeled down to the studs and is loaded with all amenities you would need for a relaxing and comfortable stay. The house has 2 queen beds + 1 queen size air mattress which sleeps up to 6 guests and Fiber High speed internet for business travelers. Located near downtown Chickasha close to the fairgrounds and sports complex with easy access to anything in Chickasha!

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, 131 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.

Guest favorite
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, 24 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 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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  2. United States
  3. Oklahoma
  4. Grady County
  5. Chickasha