Holiday rentals 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, 308 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!

Top 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
4.92 out of 5 average rating, 48 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
4.83 out of 5 average rating, 129 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
A spacious living area is presented with a gray sofa and a blue armchair, complemented by colorful throw pillows. A round coffee table sits at the center, and large sliding doors lead to a sleeping area. Kitchen amenities and laundry facilities are visible in the background.
Guest house in Newcastle
4.97 out of 5 average rating, 118 reviews

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.

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
4.86 out of 5 average rating, 37 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 gathering is set in a spacious yard, featuring a mix of wooden picnic and lounge seating. Two modern buildings with angular roofs stand in the background, surrounded by greenery and mature trees. Soft lighting from string lights adds ambiance to the outdoor space.
Guest house in Oklahoma City
5 out of 5 average rating, 133 reviews

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.

Top guest favourite
A charming two-story house is positioned on a gently sloped lot, featuring a light-colored exterior contrasted by dark blue shutters. A mature tree is situated in the front yard, providing shade, while a paved driveway leads to the garage beneath the house.
Home in Chickasha
4.9 out of 5 average rating, 40 reviews

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.

Guest favourite
A small rustic cabin is situated on a wooden deck, surrounded by lush greenery. Two donkeys and a horse are seen near the entrance. A single chair is positioned on the porch, and a vehicle is parked nearby, complementing the country setting.
Tiny home in Lawton
4.86 out of 5 average rating, 284 reviews

Tiny Cabin at the DonkeyRanch

It's a 200sqft Cabin in the middle of a 20 acre Pasture with views of the Slick Hills and Mt Scott.Minutes from lake Lawtonka and Medicine Park. Donkeys and horses roam free,as do normal country bugs and critters Plenty of room for family events and reasonable parties,,, I deleted the rest of this message.. Rent or Don't I could've sold the cabin ,but argued with Mom that people need to get off their ass and experience a different life. Safe place,except Oklahoma weather and Donkey shit

Guest favourite
Home in Chickasha
5 out of 5 average rating, 40 reviews

Rock & Roll Chickasha | Fiber | TV | W/D | Parking

The Rock & Roll is a 2 bed, 1 bath home located just 6 blocks from historic downtown Chickasha. The property was fully remodeled down to the studs and is loaded with all amenities you would need for a relaxing and comfortable stay. The house has 2 queen beds + 1 queen size air mattress which sleeps up to 6 guests and Fiber High speed internet for business travelers. Located near downtown Chickasha close to the fairgrounds and sports complex with easy access to anything in Chickasha!

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
4.95 out of 5 average rating, 115 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
An outdoor area features a spacious saltwater pool alongside a hot tub, both reflecting the evening sky. A covered patio with seating is present, offering a shaded space for relaxation. The surrounding landscape includes lush greenery and a clear view of the duplex.
Farm stay in Lindsay
5 out of 5 average rating, 31 reviews

Sunrise Suite Cedar Springs Ranch OK

Step out of your private suite to a sparkling saltwater hot tub overlooking peaceful pastures. Your suite includes a TV/DVD, full bathroom, kitchenette, and dining area—stocked for comfort. Relax in the attached sunroom with lush plants, cozy seating, and a gentle indoor fountain. Outdoor kitchen a step away! Need more space? Book both ranch Airbnb units to sleep up to 14 guests. Host lives onsite in the main home; your living areas are fully private.

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
5 out of 5 average rating, 148 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

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Quick stats about holiday rentals in Chickasha

  • Total holiday rentals

    Explore 50 holiday rentals in Chickasha

  • Nightly prices starting at

    Chickasha holiday rentals start at £23 per night before taxes and fees

  • Verified guest reviews

    Over 1,200 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Chickasha holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chickasha rentals

  • 4.7 Average rating

    Chickasha stays receive an average rating of 4.7 out of 5 from guests

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