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Holiday houses in Chickasha

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Top-rated holiday rentals in Chickasha

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
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, 329 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 favourite
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.
Home in Chickasha
4.91 out of 5 average rating, 75 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

Guest favourite
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
4.85 out of 5 average rating, 149 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 favourite
Cabin in Blanchard
4.98 out of 5 average rating, 50 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 favourite
A bright living area features light blue walls and hardwood flooring. A comfortable armchair and a small ottoman provide seating options. An entertainment unit displays a large television, and wall art adds color. A lamp stands next to the chair, providing additional light.
Guesthouse in Newcastle
4.94 out of 5 average rating, 179 reviews

Modern, Clean, Cute Private Apartment close to OU!

Guests will love staying at this entire above-home apartment that features tons of amenities to make their stay memorable. This place features a private entrance, coffee, snacks, beverages, Fast Wifi, & free parking! 15 minutes to OU & Riverwind Casino! This place also has a private, covered pavilion that is great for hanging out and cooking on our outdoor grill. Outdoor area may be shared. Our beautiful swing set located in the back yard is perfect for photoshoots or enjoying the weather.

Top Guest favourite
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
4.9 out of 5 average rating, 61 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 favourite
A charming entrance to the cottage is framed by wooden steps leading up to a covered porch. Flower boxes adorn the windows, adding greenery. A grill sits to the side, surrounded by natural landscaping, creating a serene outdoor environment.
Tiny home in Wanette
4.98 out of 5 average rating, 803 reviews

Sage Guest Cottage! Your Own Very Private HotTub!

Sage Cottage is located in the beautiful Pottawatomie County in our own Oaklore Forest. The cottage sleeps two on our queen size bed, Has a mini-kitchen and 3-piece bathroom with stand-up shower. The kitchen is equipped with a small bar sink, double hot plate, toaster, microwave, coffee pot, kuerig, toaster oven, small fridge and cooking essentials. There is a bistro table, picnic table, grill & breakfast table inside! Free Wi-Fi, Hot tub open all year, robes, see "other things to note"

Top Guest favourite
Home in Chickasha
5 out of 5 average rating, 11 reviews

Pet Friendly, Hot Tub/Sauna/Cold Plunge/Weights!

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!

Top Guest favourite
Home in Chickasha
4.99 out of 5 average rating, 72 reviews

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!

Top Guest favourite
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
4.96 out of 5 average rating, 134 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 favourite
Guesthouse in Hinton
4.97 out of 5 average rating, 211 reviews

Hidden Treasure Pool House Near I-40

If you like a little extra in your travels, you're welcome to our 1300 sq. ft. Guest Home on a 17 acre setting just 35 minutes from downtown OKC or 20 minutes from Weatherford OK. Secure location with a gated entry and some quiet scenic country but just a short drive away from the action in OKC. Great place for couples, solo adventurers, business travelers, and a family with children. NO parties or large groups. No more than 6 people on the premises.

Top Guest favourite
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, 171 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.

Popular amenities for Chickasha holiday rentals

When is the best time to visit Chickasha?

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Frequently Asked Questions

  • What are the best places to stay in Chickasha?

    Vacation rentals near downtown provide access to dining and art, while residential neighborhoods offer quieter stays for families. Some travelers choose accommodations close to the university for live events and cultural activities.

  • What are the best things to do in Chickasha with kids?

    Families with kids often visit Shannon Springs Park for playgrounds and duck ponds, explore educational programs at the Grady County Historical Society Museum, or enjoy public events and seasonal fairs. Community centers sometimes host hands-on activities.

  • What are some of the best things to do in Chickasha?

    Explore Shannon Springs Park, enjoy public art throughout downtown, or learn local history at the Grady County Historical Society Museum. Seasonal festivals and outdoor gatherings invite visitors to connect with Chickasha's community spirit.

  • How is the weather in Chickasha?

    Chickasha experiences cool winters, with lows around 27°F (-3°C) and highs near 49°F (10°C), while summers are warm with highs reaching 93°F (34°C). Rainfall peaks in spring, and autumn tends to have comfortable, mild conditions.

  • When is the best time to visit Chickasha?

    Late spring and early fall are often recommended for their milder temperatures and community festivals. Winters draw visitors seeking the festive light display, while summer brings sunny days suited for lake and park activities.

  • What are the best places to visit in Chickasha?

    Explore Shannon Springs Park for outdoor relaxation, tour the Grady County Historical Society Museum, or discover public art around downtown Chickasha. The university campus area also has local galleries and performance spaces.

  • What are some hiking trails in Chickasha?

    Chickasha has several nature trails in Shannon Springs Park, which feature walking paths, water views, and green spaces. Nearby recreation areas and local lakes also have informal routes for hiking and birdwatching.

  • What are some family activities we can do in Chickasha?

    Families often explore Shannon Springs Park, visit the Grady County Historical Society Museum, or enjoy local playgrounds and seasonal events. Community centers and nearby lakes can be enjoyable for group activities.

  • What are some of the best day trip ideas from Chickasha?

    Day trips around Chickasha can include exploring wildlife refuges, visiting regional museums, or relaxing at recreational lakes. Art galleries and small historic towns in the region also provide unique chances to engage with local culture.

  • Are there any pet friendly accommodations available in Chickasha?

    Chickasha has a selection of pet-friendly vacation rentals, particularly around central neighborhoods and quieter residential areas. Local parks like Shannon Springs Park provide outdoor spaces for walks.

  • What are some local tips for visiting Chickasha?

    Check local calendars for seasonal events and bring layers for changing weather, especially in spring and fall. Many community-run restaurants and bakeries are beloved by locals, and downtown murals offer memorable photo spots.

  • What is Chickasha known for?

    Chickasha is known for its agricultural heritage, vibrant light festival, and connection to educational institutions. Many visitors are drawn to its historic downtown, community events, and classic Oklahoma hospitality.

  • What are the best hidden gems to explore in Chickasha?

    Chickasha has colorful murals and public art downtown, as well as vintage shops and local markets where visitors often find unique items. The area is known for creative spaces and small galleries that showcase regional talent.

  • What are the best foods to try in Chickasha?

    Chickasha has menus rooted in Oklahoma classics, including chicken-fried steak, barbecue plates, and catfish. You can also explore homemade pies, Tex-Mex meals, and regional comfort foods that reflect local traditions.

  • What should I bring for a trip to Chickasha?

    Pack layers for changing temperatures, comfortable walking shoes for parks and downtown strolls, and sun protection for warmer months. If visiting during festival season or outdoor events, a light rain jacket can also be helpful.

  • What is the nightlife in Chickasha like?

    Chickasha has a relaxed nightlife scene with casual bars, live music spaces, and occasional seasonal events downtown. Some local venues around the university feature performances or open mic nights.

  • What are the most popular events or festivals in Chickasha?

    The Festival of Light transforms the community during winter with elaborate displays and family activities. Seasonal fairs, outdoor concerts, and local food events are also frequently suggested, especially in spring and summer.

  • Are there family friendly vacation rentals in Chickasha?

    Many vacation rentals in Chickasha are suited for families, with multi-bedroom layouts and kitchen spaces. Areas near public parks and community centers are often suggested for travelers with children.

Quick stats about holiday rentals in Chickasha

  • Total holiday rentals

    Explore 40 holiday rentals in Chickasha

  • Nightly prices starting at

    Chickasha holiday rentals start at $55 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,430 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chickasha holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chickasha rentals

  • 4.8 Average rating

    Chickasha stays are highly rated by guests—averaging 4.8 out of 5!

  1. Airbnb
  2. United States
  3. Oklahoma
  4. Grady County
  5. Chickasha