Chickasha holiday lettings

We found 12 holiday rentals — enter your dates for availability

Discover a selection of 8 homes and other holiday rentals in Chickasha that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include Wi-Fi and a washer and dryer. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

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Find out more about Chickasha

Find out more about Chickasha

Take in the riverfront beauty of Chickasha

The riverfront and gardens provide a pleasant backdrop to your holiday home in Chickasha. This city's baseball games, university setting and horse riding draw many visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Chickasha

Are you hoping to find things to do while you're in the area? Venture out of your cosy holiday rental and check out everything that Chickasha has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • The Maize at Reding Farm (1.5 mi / 2.3 km)
  • Winter Creek Golf Club (13.1 mi / 21.1 km)
  • Lindsay Municipal Golf Course (21.5 mi / 34.6 km)
  • Shady Grove Park (24.2 mi / 39 km)
  • Chickasaw Pointe Golf Course (2.6 mi / 4.1 km)

Exploring the natural features in Chickasha

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Chickasha is a great place to get outside. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Chickasha Sports Complex (1.6 mi / 2.6 km)
  • Shady Grove Park (24.2 mi / 39 km)
  • Austin Park (0.7 mi / 1.1 km)
  • Centennial-Kids Place Park (0.7 mi / 1.2 km)
  • 12th Street Park (1.4 mi / 2.3 km)
  • Centennial Plaza (0.2 mi / 0.3 km)

Transport options to and around Chickasha

The nearest airport is in Will Rogers World Airport (OKC), located 30.5 mi (49.1 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Oklahoma City, OK (PWA-Wiley Post), which is 37 mi (59.5 km) away.

Frequently asked questions

What is the best area to stay in Chickasha when booking a holiday rental?
When planning a holiday rental in Chickasha, Oklahoma, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming atmosphere with easy access to various local shops, cafes, and restaurants. Staying here places you within walking distance of the Chickasha Festival of Light, a popular attraction that draws visitors with its stunning holiday displays and festive spirit. Additionally, the historic Grady County Courthouse, known for its beautiful architecture, is a must-see landmark that adds to the area's appeal.

Another great option is the area surrounding the University of Science and Arts of Oklahoma. This lively district not only provides a youthful energy but also features beautiful campus grounds and cultural events throughout the year. The presence of the university contributes to a variety of rental properties, making it easier to find suitable accommodation.
How much does it cost to rent a holiday home in Chickasha?
Prices for holiday rentals in Chickasha vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chickasha to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chickasha holiday house rentals?
You can find great discounts on house rentals in Chickasha on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Chickasha?
In Chickasha, holiday houses and cottages are the most popular types of rental accommodations, with several options available in the area. These properties are typically located in quiet neighbourhoods, providing a peaceful atmosphere for travellers. Most holiday houses come with multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Cottages tend to offer a charming, rustic feel, often featuring outdoor spaces such as gardens or patios where guests can relax after a day of exploring.
Are there any family house rentals in Chickasha?
In Chickasha, Oklahoma, there are several family-friendly house rentals available, making it a suitable location for those travelling with children. The town features a variety of homes that often include spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces superb for family activities. Many properties also come with essential amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.
Can I find long-stay holiday rentals in Chickasha?
A long-stay holiday rental in Chickasha is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chickasha?
In Chickasha, there are several pet-friendly house rentals available, offering a comfortable stay for travellers with furry companions. Many of these rentals come equipped with spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy some fresh air.
Are there any remote work holiday rentals in Chickasha?
In Chickasha, Oklahoma, there are several holiday rentals suitable for remote work. Many of these properties come equipped with essential amenities such as Wi-Fi, dedicated workspaces including desks and desk chairs, providing a comfortable environment for those needing to balance work and leisure. The town itself offers a quaint atmosphere with local parks and community spaces, making it easy to take breaks and enjoy the surroundings. Additionally, with its rich history and proximity to various attractions, Chickasha serves as a convenient base for both work and exploration. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chickasha holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chickasha with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chickasha?
In Chickasha, popular rental amenities include kitchens, which allow guests to prepare their own meals, as well as patios for enjoying the outdoors. Many rentals also offer complimentary Wi-Fi, ensuring connectivity during your stay. Additionally, some properties feature secured yards, providing a safe space for children or pets to play. For those who enjoy reading, it's common to find books available in these rentals, adding a personal touch to the experience.
When is the best time to visit Chickasha for a holiday rental?
April is the most popular month to visit Chickasha, as it falls within the peak season that runs from March to May. During this vibrant time of year, visitors are drawn to the charming town for its pleasant weather and array of outdoor activities. With temperatures typically ranging in the low to mid-teens Celsius, it's ideal for exploring local parks or enjoying leisurely strolls through the historic downtown area.

This peak season is particularly favourable for those who appreciate springtime events, such as the annual Chickasha Festival of Light, which showcases the town's festive spirit. The blooming flowers and mild climate create a picturesque setting for sightseeing and outdoor adventures.

If you're looking for a more budget-friendly option, consider visiting in December. While this is a quieter month, it offers a unique charm with holiday decorations and local festivities. You can enjoy a peaceful atmosphere, making it a great time for a relaxing getaway while still taking in the town's warm hospitality.
How early should I book a Chickasha holiday rental?
Book your Chickasha holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Chickasha home rental booking on Vrbo?
To find Chickasha holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Chickasha holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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