Family-friendly 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!

Align New Private Indoor Hot Tub & Sauna Retreat

Nestled amongst The Wichita Wildlife Refuge and Downtown Medicine Park, this BRAND NEW tranquil retreat features a Private Indoor Hot tub/Pool, Private Sauna, Gym, 2 Bedrooms both with King Beds, 2 full Bathrooms with showers and a mountain view balcony. Need more space? Accommodate up to 8. Book both houses on the same property at Soak Haus Balance 5 Min Walk to Downtown Medicine Park 6 Min Drive to Lake Lawtonka 6 Min Drive to Wichita Mountains 15 Min Drive to Fort Sill 20 Min Drive to Lawton

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.

The Cottage

Newly built in December 2025, this 3-bedroom, 2-bathroom home blends vintage touches and cozy details making it easy to settle into. Located in a quiet neighborhood on the edge of town but still only 5–10 minutes from downtown, restaurants, shopping, and local attractions. Inside, the home features a kitchen with plenty of room to cook and gather. Sleeping arrangements include 2 queen beds and 2 twin beds. Step outside to enjoy the large yard. The home also includes washer and dryer access.

Country Oasis 5 minutes from Chickasha

Escape to this peaceful countryside barndominium, just 5 minutes from the Chickasha Sports Complex, Grady County Fairgrounds, and historic downtown Chickasha. Whether you’re here for a tournament, business, or a relaxing getaway, you’ll enjoy the perfect blend of comfort and convenience. The home is fully accessible and equipped with grab bars in the shower and bedroom. Enjoy the convenience of a full-size washer and dryer, well Equipped kitchen, comfortable furnishings, and ample space.

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.

Bunting Birdhouse Cottage

Stay in this unique Painted Bunting Birdhouse suite in the center of the Park, yet private! Only A few steps to shops, restaurants and the water walk make this location and getaway the perfect place to "get the feel" of Medicine Park. With a Nectar Mattress, big television, wireless internet, microwave, coffee maker and small fridge, you will have all the amenities to help you enjoy your stay! You can relax and watch the wildlife and sunset on your private front porch.

“Steele” only 3 miles to OU!

🌟 4BR | 2BA Home with Pool & Hot Tub! 🌟 Escape to comfort and style in Norman’s most desirable neighborhood! Perfect for singles, couples, or families, this home has everything you need for a relaxing stay. 💦 Private Pool & Hot Tub – unwind, relax, and soak your stress away (use at own risk) 🏡 Spacious & Modern – 4 bedrooms, 2 bathrooms, fully equipped kitchen📍 Prime Location – just 3 miles from OU— it’s ah Steele! Note: No parties, events, or gatherings permitted.

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.

Caroline's Suite

Relax with the whole family at this peaceful, cozy home. This completely updated home sleeps up to 6 people with a queen bed in one room, twin trundle beds in the other, and a sleeper couch, and a full kitchen. Stay comfortable anywhere in the house as each room has a mini split system with remotes. For your furry friends, a spacious, fenced back yard. Near USAO, Shanon Springs Park, and the Sports Complex. Quick drive to Grady Co Fairgrounds. Enjoy!

Serenity Cottage + hot tub in the country

Serenity Cottage at Red Hills Cottage Co. Slow down. Breathe deep. Make memories that last. Welcome to Serenity Cottage, a luxury shipping container retreat thoughtfully designed to help you escape the busyness of everyday life and rediscover the joy of simple moments. From the moment you arrive, you'll be greeted with fresh flowers and complimentary homemade cinnamon rolls—our way of saying, "We're so glad you're here."