Holiday houses in Chickasha

Secluded Modern Farmhouse

Room for everyone: Sleeps and dines 14 comfortably with a 2 living rooms and 2 dining rooms. No visible neighbors: enjoy sunsets, stargazing & privacy on Adirondack chairs and swings overlooking rolling hills and wildlife Tons of parking: perfect for trucks, trailers & large gatherings Entertainment galore: 75' inch TV in main room with 50' inch TVs in all the bedrooms but one; poker table & foosball table invite friendly competition. As pictured: two separate buildings 15 yards apart

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

Your Private Pond Paradise with 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!

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 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.

Relax & Recharge | Hot Tub | Sauna | Cold Plunge

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!

Private Pond | Peaceful Retreat | Dog Friendly

Escape to a peaceful 475 sq ft countryside cottage with your own private pond, fountain, goldfish, and two kayaks for the pond. Relax on two spacious patios, including one overlooking the water. Enjoy quiet mornings, beautiful sunsets, and star-filled nights. Dogs are welcome, and there's plenty of room for horse trailers and riding. Conveniently located near Winter Creek Golf & Social Club and Grady County Fairgrounds, yet private enough to feel like your own hidden getaway.

Bohemian Bungalow *no cleaning fee*

We have spent the last several years traveling the country & curating an eclectic collection of treasures: vintage National Park souvenirs, swag lamps, and unique art. We rotate art often, so every visit may yield a new treasure to discover! The kitchen table is a great place for your work-from-home needs, but there is a foldable desk in the bedroom closet if you need a private space. We can often accommodate a no-charge early check-in, so please do not hesitate to ask!

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."

Detached apartment/by USAO

Visit small town Chickasha! See the 50ft Leg Lamp, eat&drink at 1 of many thriving places in town&more! Easy drive to OKC. ☆.3 mile to USAO ☆ROKU TV w/Netflix, Disney,more ☆Wifi ☆driveway parking ☆fenced in yard -full size air mattress -keyless entry -USB outlet Upstairs unit above the garage. No elevator. Dog friendly on case-by-case basis. Pet fee. The yard is shared with our house. NO smoking, e-cigs, vapes.