7 properties  

2 Bedrooms • 1 Bath • Sleeps 1-6
Allows pets Internet Fireplace Downtown

Welcome to The Good Vibes!

This dog-friendly, fully remodeled 2 bedroom home is located 8 blocks from historic Downtown Chickasha and minutes from the famous 50-Foot Leg Lamp, Fairgrounds, Sports Complex & USAO. Enjoy fiber WiFi, a full kitchen, Smart TVs, washer/dryer, private fenced outdoor space and plenty of parking for cars, trucks & trailers. The home comfortably sleeps 4 in beds, with a queen air mattress available to accommodate up to 6 guests.

Beds for 4 • Accommodates Up to 6 • 2 Bedroom • 1 Bathroom • Dog Friendly • Fiber WiFi • Free Parking

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4 Bedrooms • 2 Baths • Sleeps 1-10
Internet

Ralphie’s House – A Christmas Story Stay in Chickasha

“You’ll shoot your eye out!” …but the only thing you’re in danger of here is booking an extra night.

Welcome to Ralphie’s House—your cozy, nostalgic getaway in Chickasha, where the Christmas spirit lives year-round. Just a short stroll from the town’s iconic 50-foot leg lamp, this fully renovated 1930s home blends modern comfort with playful nods to A Christmas Story.

Step inside and discover why guests say staying here feels like a “major award.”

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2 Bedrooms • 1 Bath • Sleeps 1-6
Internet Fireplace

Welcome to The Rock & Roll!

Hosted by a full-time touring musician, this fully remodeled 2 bedroom home is just 8 blocks from Historic Downtown Chickasha and minutes from the famous 50-Foot Leg Lamp, Fairgrounds, Sports Complex & USAO. Enjoy fiber WiFi, a full kitchen, Smart TVs, washer/dryer, private outdoor space and plenty of parking for cars, trucks & trailers.

Beds for 4 • Accommodates Up to 6 • 2 Bedroom • 1 Bathroom • Dog Friendly • Fiber WiFi • Free Parking

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2 Bedrooms • 1 Bath • Sleeps 1-6
Allows pets Internet Fireplace Downtown

Welcome to The Charm!  This spacious 850 sq. ft., dog-friendly 1BR home is just 6 blocks from Historic Downtown Chickasha and minutes from the 50-Foot Leg Lamp, Fairgrounds, Sports Complex & USAO. Enjoy fiber WiFi, a full kitchen, Smart TVs, washer/dryer, private outdoor space and plenty of parking. Beds for 4 + accommodates up to 6!

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1 Bedroom • 1 Bath • Sleeps 1-6
Internet Downtown

Escape to The Cozy, a newly remodeled 1-bedroom home in Chickasha, just blocks from historic downtown. This 850 sq ft space comfortably sleeps up to 6 guests with a queen bed, futon, and air mattress. Enjoy a fully equipped kitchen, high-speed fiber WiFi, 2 - 60” Smart TV's, and a private yard with a BBQ. Perfect for Couples, small families or work trips, with free private parking for trucks and trailers. Your ideal base for exploring the area, just a 35-minute drive from Will Rogers World Airport.

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3 Bedrooms • 2 Baths • Sleeps 1-8
Internet

The Drover House is a large 3 bed, 2 bath home with a private swimming pool located just 5 blocks from USAO College Campus. The property is newly remodeled and features all the amenities you need for a relaxing and comfortable stay including a private in-ground swimming pool . Located on a very quiet street with easy access to anything in Chickasha!

2 mins → USAO College
5 mins → DT Chickasha + 50 Ft Leg Lamp + Festival of Light
35 mins → Will Rogers World Airport
40 mins → Wichita Mountains / Medicine Park (swimming, hiking, camping)

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3 Bedrooms • 2 Baths • Sleeps 1-8
Internet

Welcome to The Pinewood House

Step into the perfect blend of historic charm and modern comfort at The Pinewood House—a beautifully restored 1930's home featuring original pine floors and a full 2026 renovation. Whether you're visiting Chickasha for a weekend getaway, a USAO event, the Fairgrounds or to see Chickasha’s iconic 50-ft Leg Lamp, this thoughtfully designed home offers a warm, inviting space to relax and reconnect. Located just 2 blocks (Walking Distance) from USAO college.

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