Holiday rentals in Bennington

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Top-rated holiday rentals in Bennington

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

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Top guest favourite

A brick home is situated in a spacious yard, surrounded by meticulously maintained greenery. The front features two prominent trees and a decorative shrub border. A pathway leads to the elegant entrance, framed by large windows that invite natural light into the interior.

Home in Durant

Just Like Home - Near Choctaw Casino - Wk/ Mo Disc

Brick Home in Quiet Community with three bedrooms, kitchen, dining area, master with jetted tub, two other bedrooms, living room, two car garage, laundry room, covered patio, storm shelter and fenced backyard. Attractions: Choctaw Casino - 10 min Lake Texoma State Park - 19 min Chickasaw Pointe Golf Club - 18 min Southeastern Oklahoma State University - 10 min Ole Red - Blake Sheldon's Restaurant/ bar in Tishamingo - 38 min Disc for weekly or monthly! Please contact us if you have questions.

4.98 out of 5 average rating, 295 reviews

Top guest favourite

Home in Denison

Cliffside Cottage

Welcome to your private escape in the woods! Nestled in a quiet, secluded setting with a scenic views and gated entry, the home feels like a true retreat while offering upscale amenities. Relax by the private heated pool surrounded by expansive concrete decking, and 2 put-put courses. Outdoor lounge and seating areas ideal for morning coffee or sunset cocktails. Gas grill, and umbrellas by the pool, this home has it all! Age must be 25 yrs+ to book. No more that 6 guests on property at any time.

4.95 out of 5 average rating, 42 reviews

Guest favourite

The cabin exterior is crafted from natural wood, featuring a light yellow door and a single window with a simple curtain. A roof extends outward, providing shelter over a concrete porch area, surrounded by greenery and gravel.

Cabin in Boswell

Wood Guest Ranch Waterfront Issoba Cabin

One bedroom, one bath cabin, with sofa sleeper in living room (suitable for children) and kitchenette. The cabin comes equipped with a coffee pot, microwave, compact refrigerator, electric skillet and spatula, dishes, utensils, dish soap, dish drain, linens and towels (for indoor use only). We do not provide any additional cooking supplies. Outside the cabin has a picnic table, fire pit, and grill. Please bring your own charcoal, lighter fluid, matches/lighter, and outside cooking utensils.

4.88 out of 5 average rating, 104 reviews

Top guest favourite

A single-story house with a metal roof is seen set against a clear blue sky. Surrounding greenery includes a tall pine tree and a large, bare tree. A gravel driveway leads up to the home, which features a covered porch along the front.

Home in Durant

Roadrunner Retreat

Come enjoy our peaceful country getaway on 10 beautiful acres. I've tried to basically make our place all inclusive, so you may just want to come enjoy all it has to offer as your vacation itself. Located 15 minutes from Choctaw Casino, Westbay Casino, Texoma casino, and Lake Texoma. Newly renovated 3 beds/2 baths(1 king and 2 queens) Fully stocked kitchen(pots,pans, cups,plates, etc. Stocked bathrooms ( toiletries included ) Free wifi and Netflix Pets welcome (Garage not part of the rental)

4.99 out of 5 average rating, 137 reviews

Luxe

An aerial view of Rockin’ J Ranch captures the sprawling layout of the property, featuring a luxurious ranch house with a gray roof, surrounded by lush greenery and mature trees. The infinity pool and landscaped areas are visible, along with the private lake reflecting the distant sunlight.

Ranch in Choctaw County

LUX Ranch on 2,600 acre playground! Swim Fish Hunt

Welcome to Rockin’ J Ranch, a luxurious retreat nestled on 2,600 acres of pristine land with its own private stocked lake, infinity pool, and endless options for adventure. Whether you’re seeking a peaceful getaway, hosting an unforgettable event, or leaving your cares behind through outdoor adventures, this ranch offers an unbeatable experience of Oklahoma countryside luxury. The ranch is located conveniently close to the Choctaw Casino in Durant, so within a 35-40 minute drive you can have a

4.94 out of 5 average rating, 17 reviews

Superhost

Tiny home in Durant

The Whisker Biscuit

Located just 4 miles from Choctaw Casino & Resort Durant and 17 miles from Lake Texoma, this tiny home gives you the best of both worlds: quick access to excitement and peaceful countryside. Set on 7 beautiful acres, you will stay right on a serene pond, with fishing just steps from your back door. Enjoy the wraparound patio with a private hot tub, outdoor TV, grill & fire pit. Whether you’re here for a casino weekend or time to recharge, the Whisker Biscuit is a cozy and unique getaway!

5.0 out of 5 average rating, 4 reviews

Top guest favourite

A rustic living area features warm wood paneling and a comfortable seating arrangement. A flat-screen TV is mounted on the wall across from a cozy chair and an accent table. Soft lighting is provided by a table lamp, creating a welcoming environment.

Farm stay in Durant

The Roosting Place 12 mins from Choctaw Farm Stay

Unwind as you listen to the peaceful sounds of country life, including the gentle clucking of our resident chickens. Take a short walk down to one of two ponds where you may encounter friendly farm animals, always happy to receive a treat. The Roosting Place, a one-bedroom, one-bath apartment, provides the perfect escape to experience the tranquility of the countryside. Enjoy outdoor activities such as hiking, fishing, bird watching, or simply wandering the grounds to connect with nature.

5.0 out of 5 average rating, 59 reviews

Guest favourite

An aerial view of a modern countryside manor reveals a large pool surrounded by a stone patio. The structure features a combination of stone and wood textures, with large windows overlooking the green landscape. Lush grass and trees extend in the background.

Home in Calera

Countryside Manor with Pool

Relax, unwind and recharge at our beautiful countryside manor that sits on 20 acres. Located 4 miles from Choctaw Casino and 4 miles from Lake Texoma! Chefs kitchen to feed the masses. 3 beds and 2.5 baths Pool with patio to entertain you and your guests. Traeger grill for all your bbq needs. Horses, pups and chickens roam freely. DISCLAIMER: Our property manager lives in the back house 100 yards from the house. You will have your privacy, but is there for any immediate needs.

4.94 out of 5 average rating, 47 reviews

Top guest favourite

The exterior of the cozy cabin is presented, featuring a welcoming porch with wooden railings and steps. Flower pots adorn the entryway, and a swing can be seen alongside two chairs on the porch, with a vast expanse of pasture in the background.

Farm stay in Bennington

Where The Blacktop Ends 225 acres to explore!

We provide a cozy space that offers a blend of rustic charm and modern amenities. Breathtaking views of rolling pastures filled with grazing cattle and mini donkeys, allowing guests to immerse themselves in the natural beauty of the country. Enjoy outdoor activities such as hiking, birdwatching, fishing, or simply enjoying smores around the campfire. We provide guests with a unique opportunity to unwind, reconnect with nature, and create cherished memories during their stay.

5.0 out of 5 average rating, 29 reviews

Top guest favourite

Home in Durant

Rodeo Ranch 55 acres, 3 Bdr, Pool, 1/3 mile/casino

Relax at Rodeo Ranch near the casino. Beautiful 3 bdr and 2 bath house on 55 acres for privacy and relaxation. The house has a Pool, Corn Hole and more for you to enjoy during your stay. Located 1/3 of a mile from Choctaw in Durant, OK, making it a great place for concerts and other events at the casino. The house has new decorations and furnishings. Great place to just relax and enjoy your time in the Durant area. Pool is in service by mid-May.

4.88 out of 5 average rating, 263 reviews

Top guest favourite

A wooden lodge is reflected in the calm water of a pond, surrounded by lush greenery. The structure features large windows and multiple decks, offering access to the serene outdoor space. A smooth stone border lines the pond, enhancing the natural setting.

Home in Bennington

Waterfront Cabin, 4BR/5BA with Magical Pond Views

Escape to Enchanted Ponds, a stunning waterfront lodge on 28 peaceful acres. Overlooking a 4-acre stocked pond, enjoy catch-and-release fishing, kayaking, and stargazing. Relax on two spacious decks, gather around the firepit table, or challenge friends to horseshoes. Marvel at the towering 70-foot wind chime and watch for deer. Just 30 minutes from Choctaw Casino in Durant or Grant—this magical countryside retreat blends adventure with serenity.

5.0 out of 5 average rating, 15 reviews

Top guest favourite

A charming home is set against a backdrop of trees, featuring a light-colored exterior and a welcoming front porch. A landscaped yard with green grass and colorful flower beds enhances the appeal. A driveway leads up to the attached garage on the left.

Home in Antlers

Charley's Vacation Rental

This home away from home is the best alternative to hotels and motels whether you are in town for business, a holiday, or a special event. This family home is close to the small town center known to be the gateway to all of the beauty of southeast Oklahoma. Whether you are on business, visiting family, hunting or enjoying many of the different events scheduled throughout the year, you can count on a this comfortable cottage to provide refuge.

4.97 out of 5 average rating, 713 reviews