Holiday rentals in Drumright

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Top-rated holiday rentals in Drumright

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

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Top guest favourite

An aerial view captures the spacious property set against a backdrop of mature trees and open landscape. The newly remodeled home features a large, dark roof, a garage, and a beautifully constructed outdoor space that includes a regulation-size pickleball court with a blue enclosure.

Home in Cleveland

4.99 out of 5 average rating, 134 reviews

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!

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Top guest favourite

The front view of the farmhouse features a green metal roof and a spacious porch with seating. The porch is enclosed by wooden railings and includes a small table. Lush greenery surrounds the house, enhancing its countryside charm.

Farm stay in Cushing

4.98 out of 5 average rating, 54 reviews

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.

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Guest favourite

Cabin in Cushing

5.0 out of 5 average rating, 10 reviews

Family & Team Retreat | Sleeps 14 | Pond + Arcade

Adventure Acres Log Cabin – Zipline, Arcade, Fishing & More! Escape to 35 private acres near Route 66 in Cushing, OK! Sleeps 14 and features a fishing pond, zipline, obstacle course, playground, arcade, pool table, air hockey, hiking trails, Bluey-themed kids' room, princess room, hidden reading nook, wildlife watching, and outdoor games. Perfect for families, reunions, graduation weekends, sports teams, and group getaways. Keep everyone together instead of booking multiple hotel rooms!

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Guest favourite

Cabin in Cushing

4.85 out of 5 average rating, 27 reviews

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.

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Guest favourite

Guest house in Mannford

4.91 out of 5 average rating, 35 reviews

Cozy Home Near Keystone Lake| 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!

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Superhost

The exterior view of the remodeled farmhouse showcases a well-maintained landscape with a variety of plants and decorative stones. A wide concrete driveway leads to the entrance, and large windows offer glimpses of the surrounding grassy fields.

Home in Tryon

4.95 out of 5 average rating, 148 reviews

Peaceful Farmhouse north of Chandler

Wi-Fi 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.

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Top guest favourite

Home in Bristow

4.87 out of 5 average rating, 214 reviews

Bristows private home for rent

Stay in Bristow's newest guest house. Perfect for families. We have an outdoor smoking area and fenced in backyard with a propane grill. Unfortunately, at this time we do not allow any pets. This is a family friendly home; however, we do not provide any type of baby equipment. You are welcome to bring infants as long as you bring any items needed. I live right next door so if you have any issues, please let me know. Extra guest fee After 4 guests, $35 per person, per night

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Top guest favourite

The exterior of a two-story colonial-style house is shown, featuring a covered front porch supported by two large columns. A light-colored facade is complemented by green landscaping and a pathway leading to the entrance. A railing encircles the porch area.

Home in Cushing

4.98 out of 5 average rating, 49 reviews

Crossroads Columns

Crossroads Columns is a charming spacious 2 story colonial style house. 4 bedrooms with 4 Queen size, trundle with 2 twins. 2 large living room spaces with 2 sectional sofas. A dining room great for dinners or Conferences. Beautiful kitchen with Coffee bar/Toaster/microwave. This house is equipped with pots and pans, Dishes glassware/ utensils. office space, Wi-Fi. Washer and dryer. Outside security cameras. One full bath and shower downstairs. Upstairs only bath.

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Top guest favourite

Home in Cushing

4.93 out of 5 average rating, 14 reviews

Tatanka Run

Skip the hotel and enjoy more space for less! This remodeled 3-bedroom, 1-bath home is perfect for families, work trips, and weekend getaways. Relax in the cozy living room, cook in the updated kitchen, and enjoy the convenience of laundry and a versatile garage for parking or extra seating. Located less than a mile from downtown Cushing, 30 minutes from Stillwater, and about an hour from Tulsa and Oklahoma City. Your home away from home awaits!

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Guest favourite

An open concept living area showcases a spacious layout with comfortable seating arrangements. A coffee table sits at the center, surrounded by two armchairs and a sofa. A dining table is visible in the background, with modern lighting fixtures enhancing the space.

Home in Bristow

4.95 out of 5 average rating, 151 reviews

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.

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Guest favourite

A serene landscape is presented with vibrant clouds at sunset, casting warm hues across the sky. A flagpole stands in the foreground, surrounded by well-maintained grass, with wooden fencing outlining an open area. Trees are visible in the background, enhancing the natural setting.

Ranch in Stroud

5.0 out of 5 average rating, 10 reviews

Heart Diamond Estate

Get cozy and settle into this rustic space. This unique 1 bedroom, 2 bed barndominium is your horse property away from home. Complete with ponds, sweeping vistas on 160 acres of prime Oklahoma rolling hills, trails and abundant wildlife. Horse stalls available with prior approval.

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Guest favourite

A dining area is depicted with a round wooden table surrounded by black chairs. Route 66 décor is present on the wall, along with a motorcycle-themed accent. A doorway leads to a bathroom, and a door opens to an outdoor space.

Home in Bristow

5.0 out of 5 average rating, 46 reviews

The Oaks on Route 66!

Enjoy Route 66 and make yourself at home! Just 3 miles north of Bristow, OK, this 3-bedroom, 2-bathroom open-concept home offers covered parking and a peaceful escape. Surrounded by nature and Route 66 charm, it’s the perfect spot to relax with family and friends!

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