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Vacation rentals in Chickasha

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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, 364 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, 319 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
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.

Top guest favorite
The outdoor space features a swimming pool surrounded by a fenced yard, with a covered patio area equipped with chairs and a grill. The house has a rustic brick exterior, complemented by trees and a scenic view of the nearby hills.
Guesthouse in Lawton
5 out of 5 average rating, 278 reviews

No Cleaning Fee. Home near Post and the Refuge.

Furnished 1,000 sq ft. home, recently re-modeled and includes conveniences designed to meet the needs of families looking for a quiet and relaxing get-away with their Soldier, busy professionals, or those enjoying a vacation. I want this house to be your "home away from home" . So you do not need to bring your iron, bath, or kitchen items! This home is located 10 miles from Lake Lawtonka, Ft. Sill and Wichita Mountains Wildlife Refuge. Pool open mid May to early June Pool closed October.

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
A spacious living area is presented with a gray sofa and a blue armchair, complemented by colorful throw pillows. A round coffee table sits at the center, and large sliding doors lead to a sleeping area. Kitchen amenities and laundry facilities are visible in the background.
Guesthouse in Newcastle
4.98 out of 5 average rating, 126 reviews

Adorable Private Guest House, Quiet, Clean, Wi-Fi!

Guests will love staying at this entire guest house that features tons of amenities to make their stay memorable. This place features a private entrance, coffee, snacks, beverages, Fast Wifi, free parking, and more! Located close to University of Oklahoma & Riverwind Casino! This place also has a covered pavilion that is great for hanging out and cooking on our outdoor grill. Our beautiful swing set located in the back yard is perfect for photoshoots or enjoying the weather. May be shared.

Top guest favorite
Cabin in Blanchard
4.97 out of 5 average rating, 32 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
4.88 out of 5 average rating, 51 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
The exterior of a converted grain bin is displayed, featuring a large sunflower mural. A welcoming porch with rocking chairs is positioned to the side, surrounded by lush green grass and vibrant flower beds, enhancing the rural charm of the property.
Tiny home in Elgin
5 out of 5 average rating, 110 reviews

The Painted Silos - The Sunflower Bin

Nestled in Elgin, Oklahoma, this converted grain bin offers a unique experience. A short drive from Ft. Sill, Medicine Park and the Wichita Mountain Wildlife Refuge. Featuring modern amenities with a rustic charm, this silo has been tastefully decorated and outfitted with all the luxuries you need for a cozy stay. This charming silo sleeps up to four and includes a stylish living area, fully equipped kitchen, dining area, one spacious bedroom, cozy built in bunk beds, and 1.5 bath.

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, 127 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
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, 161 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
A private outdoor area features a circular in-ground pool surrounded by a stone patio. A grill is positioned near the pool house, complemented by potted plants and a wooden fence providing privacy. The space is shaded by overhanging trees, creating a serene atmosphere.
Home in Duncan
4.94 out of 5 average rating, 190 reviews

McNair Westgate House, Golf Oasis, Pool, Hot Tub

Experience the newly remodeled Westgate House, a private oasis in Duncan. This 3BR, 2.5 bath, 2472 sq ft, home features a HOT TUB, in-ground pool, pool house w/bar, high-end kitchen appliances, whiskey lounge with arcade table. The master bedroom offers exclusive access to a private patio and pool. Sleeps 6 guests comfortably. Conveniently located near Stephens County Fairgrounds, Casino, Brewery & Kiddieland Park.

Popular amenities for Chickasha vacation rentals

When is the best time to visit Chickasha?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$17,773 GYDG$17,773 GYDG$18,610 GYDG$19,655 GYDG$19,655 GYDG$20,282 GYDG$19,655 GYDG$18,400 GYDG$18,819 GYDG$18,400 GYDG$18,819 GYDG$18,400 GYD
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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 G$8,364 GYD 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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