Holiday rentals in Chickasha

⭐️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!

Grandma’s House | Cozy & Close

“Grandma’s House” is home away from home! Conveniently located down the street from Centennial Park, & 1 mile from the Leg Lamp, Festival of Light, Fairgrounds, USAO, & Sports Complex! As you step inside, you’re immediately taken back in time to your grandma’s house - greeted by a cozy living room & kitchen. The bathroom features a walk-in shower & a wooded ceiling for an extra touch of charm. Step outside on the patio to unwind for the evening. This place will surely make you feel right at home

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

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.

Boutique Retreat w Private Deck! La Sombra Studio

This modern studio garage apartment is a quiet retreat on 2.5 acres within 15 minutes of Downtown Oklahoma City! If you are looking for boutique experience away from the noise but still accessible to everything the city has to offer the La Sombra Studio is the spot. Perfect for the couple looking to get away, business travelers, or a solo retreat. You will have a private deck with perfect sunset views, fire-pit, outdoor shower for warmer weather, & a table for meals or even working outside.

Cute house in Chickasha

This charming 1 bedroom, 1 bathroom house is perfect for a small family. It is furnished with everything you will need for your stay including a sleeper sofa that folds out to a queen bed. There is a designated work area off of the living room with enough space to use for a dressing room. Enjoy the spacious backyard while you sit on the deck. This house is centrally located and just minutes away from downtown Chickasha where you can find yummy places to eat and fun places to explore.

The Prancing Pony

The Prancying Pony is a short walk to the University of Oklahoma Campus, Historic Downtown Arts District, restaurants, and dining. The Pony is a quiet and secluded cabana with beautiful garden and pool. The ambiance, the outdoor space, and neighborhood make this the ideal location for exploring the best of Norman. This apartment is good for couples, solo adventurers, and business travelers. The apartment has one, gated parking spot. Also included is the use of an outdoor grill.

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.

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.

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.

Cozy Modern Cottage, fenced yard

This new home was built in Spring 2025. Granite counters and upgraded flooring throughout. This Airbnb comes with everything you need for a comfortable stay including a stocked kitchen, 65" TV, soap, shampoo and everything else you need for a relaxing stay. Downtown Chickasha is just 7 miles away where you can find restaurants, shopping and more. Ask about our military discount!

Sooner Suite - Private Entry & Close to OU!

Come and go as you please from this completely remodeled private entry suite. Quiet neighborhood less than 1 mile to south campus. Enjoy a queen size platform bed and walk-in shower. Cozy and clean. Your space shares a wall with our home’s den. (with newly installed insulation and a solid core door to deter sound though we can’t guarantee you won't hear our small children.)