Vacation rentals in Grady County

4.97 out of 5 average rating, 300 reviews

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

⭐️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!

A modest exterior of a charming house is presented, featuring light-colored siding and dark shutters. The entryway is framed by a wooden porch supported by two columns. A small bench sits beside the door, surrounded by greenery and mature trees.

4.9 out of 5 average rating, 40 reviews

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

Superhost

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.

4.83 out of 5 average rating, 126 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

4.85 out of 5 average rating, 73 reviews

A single-story brick house is set within a grassy area, featuring a central chimney. Large windows allow natural light to fill the interior. Surrounding trees provide a natural border, and a concrete pathway leads to the entrance, welcoming guests to explore the space.

Home in Verden

The Ranch

Country living at its best! Come see the night stars unobstructed from tall buildings. Hear the coyotes howl and the crickets chirp. There are two living spaces with several sofas for plenty of room. Fiber internet and tv. The heat and air unit has been replaced. There are 2 complete bathrooms with 2 showers, 2 toilets, 2 sinks. We don’t add cleaning fees to your stay. We have pens that could house your horse or show calf or lambs. Please get with us ahead of time so we can make arrangements.

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.

4.87 out of 5 average rating, 31 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.

The image features the entrance of a single-story house with a navy blue door. A small set of concrete steps leads up to the door, surrounded by blooming yellow flowers and lush greenery. Light filters through the windows, adding to the inviting appearance.

4.95 out of 5 average rating, 19 reviews

Charming Bungalow

Relax with the whole family at this peaceful place to stay. The comforts of home while you’re away. We will consider small pets upon approval, with small additional pet fee. Wonderful neighborhood. Close to the college or downtown. Lots of good restaurants in the area or use the backyard to grill. Kitchen has a Keurig with coffee and tea, toaster, crockpot, dishes, and the essentials. The backyard is fenced. Walking distance to the festival of lights and USAO. The fairgrounds are only 3.6

A charming two-story Craftsman house is featured, adorned with festive lights along the eaves. A vintage red truck is parked in the driveway beside well-maintained landscaping. The expansive yard provides a grassy area, enclosed by a wooden fence, creating a welcoming outdoor space.

5 out of 5 average rating, 27 reviews

Ralphie's House Chickasha | FAST WIFI | Brand New!

We're EXCITED to offer Ralphie's House "A Christmas Story" themed property in Chickasha OK! Chickasha's Festival of Light was voted in the top light displays in the Country and recently built the worlds tallest 50 foot Leg Lamp in Historic Downtown. Ralphie's is located just 6 blocks from downtown. It only made sense to keep the Christmas spirit alive year round and do a Christmas themed property! The two story House was built in 1930 and fully remodeled in 2024, everything is brand new.

Superhost

A welcoming living area features a comfortable white sofa with assorted cushions in blue and yellow. Two upholstered armchairs in a rich teal color complement a dark coffee table. Natural light enters through large windows, framed by navy curtains, creating a cozy atmosphere.

Apartment in Chickasha

4.88 out of 5 average rating, 33 reviews

Lala's by Hope two Bedroom Downtown Chickasha OK.

Lala's by Hope is a warming 2 bedroom Apt. Located in the Historic Down Town Chickasha with walking distance to shops and restaurants. Lala's is centrally located close to Grady County Fairgrounds, Shannon Springs Park, known for The Festival of Light, Chickasha Sport Complex, USAO, and the amazing Canadian River Brewing Co. This is a perfect & welcoming place for families on vacation, sports and Fairgrounds event as well as traveling workers. This is a perfect short-term rental.

4.94 out of 5 average rating, 108 reviews

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

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.

Shipping container in Chickasha

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.

5 out of 5 average rating, 138 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.

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.

5 out of 5 average rating, 17 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.