Holiday rentals in Drumright

Historic Route 66 Guesthouse

Cozy guest house on historic Route 66 ideal for bikers, bicyclists, road trippers. Private entrance, access to secure backyard including available covered parking, hot tub, grill, fire pit, 1 king and 1 queen bed, private bathroom with small tub & shower, WiFi, TV, refrigerator, microwave. Within walking distance of large city park with fishing lake, golf course, disc golf, skatepark, tennis courts, & seasonal swimming pool. Kitchen not suitable for cooking but abundant local takeout available.

The Farmhouse Lovely 2 bedroom Fishing available

Relax with the whole family at this peaceful place to stay. Country living with abundant wildlife and catch and release watershed lake (no swimming). Plenty of wildlife photo opportunities. 11 miles north of Route 66 And 4 miles from Stroud Lake. 48 min. from Stillwater and Okla. State University, about an hour from Okla. City and Tulsa. Covered parking. No Smoking, Vaping, or marijuana use in the house. Want to craft? I have 2 Cricut machines and cartridges. I’m sorry we no longer allow pets.

Skyline Paradise | Pickleball & Bball |Keystone Lk

Luxury Retreat with Tournament-Grade Pickleball Court Experience this stunning hilltop oasis near Keystone Lake, featuring a brand-new (2025) regulation-size pickleball court with pro lighting, a basketball area, & endless entertainment —cornhole, jumbo Jenga, arcade games, air hockey, foosball & more! • 3,200 sq. ft. on 3.5 acres • Stocked kitchen • 30 min to downtown Tulsa • Three-level deck with breathtaking views • Dog-friendly (3 under 80 lbs, $125 fee) Book now for the ultimate retreat!

Peaceful Farmhouse north of Chandler

Wi-Fi Pet friendly Close to I-44 between Oklahoma City and Tulsa 3 acre fenced yard Our guests have described our 280 acre farm as: Majestic Breathtaking Immaculate Scenery felt like a movie scene Stunning Sunsets, Sunrises and Stars Gorgeous valley view Country solitude Welcome to a peaceful escape in our beautifully remodeled farmhouse with views of the picturesque mile long valley. Enjoy watching the cattle and donkeys in the pasture and the other wildlife that make their home here.

New Country Cabin Fenced Yard

Country living in a secluded spot- newly built with custom cowboy/rustic features. Shaded fenced back yard, 3 bedrooms-2 full baths- one with walk in shower, one with shower/tub combo (huge tub) Twin Bunk beds, 2 Queen beds, Sofa recliners & 2 electric recliners, Parking in front. Covered front porch, Washer/Dryer, Salt Water filtration system, ceiling fans, 2 mini splits for heat and air. About 7 minutes from town on a gravel road. Access to television in all 3 bedrooms, and free Wifi.

Crossroads Cottage in Cushing

Crossroads Cottage is a clean, charming 2-bedroom, 2-full-bathroom house. It has a spacious kitchen with a full-size refrigerator, a stove with oven, a microwave, and a coffee maker. This house is equipped with pots and pans, a toaster, glassware, and utensils. There is a separate dining room and living room with a large flat-screen TV, an office space, a laundry room, and a beautiful private courtyard, great for barbecuing. It has central heat and air and outside security cameras.

Keystone Lake Retreat | 2BR | Family Friendly

Rustic 2BR guesthouse just 5 min from Keystone Lake! Perfect for families, couples, or friends seeking lake fun. Full kitchen, cozy gathering space, and private outdoor yard with pup-friendly amenities. Explore Keystone Lake just moments away! Enjoy fishing, boating, or scenic lake days. Ideal weekend escapes, a quick getaway, or tranquil stays near the water. Enjoy a full kitchen with essentials, includes Wi-Fi, laundry, coffee setup. Only a short 30 minutes from downtown Tulsa!

New Modern Charm on Route 66

Come relax in this newly constructed home located on Historic Route 66. This 3 bedroom 2 full bathrooms open concept is the perfect spot for family or friends. Right around the corner from The Bristow Lake and City Park with great views to enjoy! The Park and Lake offer the perfect place for walks, runs and/or bike rides. Also just minutes to downtown for some local shopping and dining. House also has attached single car garage for security.

Faye's Cottage

Our place is 15 minutes from Oklahoma State University, Lake McMurtry East is 3.5 miles away. You’ll love our place because of the outdoors space, tranquility and the wildlife. Our place is good for couples, solo adventurers, and business travelers. Enjoy the stars and nights around the fire pit. Taxes are less out here too - you don't have to pay the 4% city or 7% accommodation taxes when you book with us since we're outside city limits.

Geodesic Sunset Dome at Three Ponds Community

This cozy geodesic dome has its own private nook overlooking our second pond. Heating and air are a must in Oklahoma and we got you covered so you are comfortable all year long. You also get access to our beautiful outdoor shower and our unique compost toilet for a truly memorable experience. Included in the dome is a mini fridge, microwave, Kuerig coffee, along with bowls, utensils, and towels.

Orange Acres/New*Private2BR/2B Duplex/Pet friendly

If you're looking for a clean, quiet, cozy place to stay while visiting Stillwater, we have the perfect spot for you. Orange Acres is perfect for anyone wanting to experience a peaceful country life, with the closeness(less than 3 miles) to downtown shopping, dining and sightseeing. We are also less than 5 miles from OSU campus. We are now Pet Friendly!! We can’t wait to host you!! 🧡🖤

The Scissortail Farmhouse - LAND, HOT TUB, horses!

Looking for a serene escape in a convenient location? The Scissortail Farmhouse is a new guest home nestled on the edge of a working regenerative farm that supplies produce to many of our best local restaurants. It is minutes from the airport, downtown, and popular Tulsa attractions. We hope you enjoy our little slice of country that is about as close as you can get to the big city!