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

4.98 out of 5 average rating, 295 reviews

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.

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Top guest favourite

Tiny home in Durant

4.98 out of 5 average rating, 55 reviews

Lucky Love Lodge

Located just 4 miles from Choctaw Casino & Resort Durant and 17 miles from Lake Texoma, this one-of-a-kind tiny home gives you the best of both worlds: quick access to excitement and total privacy when you’re ready to unwind. Set on 7 beautiful acres, the lodge sits right on a serene pond & you can go fishing just steps from your back door. Whether you’re here for a fun casino weekend or just some time to recharge, Lucky Love Lodge offers a unique stay that feels both cozy and unforgettable!

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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

4.88 out of 5 average rating, 104 reviews

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.

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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

4.94 out of 5 average rating, 17 reviews

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

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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

5.0 out of 5 average rating, 29 reviews

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.

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Top guest favourite

Home in Durant

4.88 out of 5 average rating, 262 reviews

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.

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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

5.0 out of 5 average rating, 15 reviews

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.

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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

4.97 out of 5 average rating, 711 reviews

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.

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Top guest favourite

A cabin with a wooden exterior is set amidst a green lawn, flanked by trees. The front porch features steps leading up, and seating is visible. Surrounding flower beds add color to the landscape, while a gravel path provides access to the entrance.

Cabin in Ravenna

4.93 out of 5 average rating, 263 reviews

GORGEOUS COUNTRY CABIN JUST NORTH OF DALLAS!!!

BEAUTIFUL COZY CABIN FOR YOUR FAMILY!!! This beautifully decorated 700 sq ft. cabin has everything you need for your perfect getaway. Just a 45 minute drive north of McKinney located on 2.5 acres. You can sit back and enjoy the view of the trees while rocking of the front porch with your morning coffee. Located only 10 miles from Lake Bonham, this cabin has a full kitchen equipped with everything you need for a country escape.

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Top guest favourite

The rustic cabin features a wooden exterior with large windows offering views of the surrounding landscape. A covered porch with rocking chairs provides outdoor seating. Flat, grassy areas extend around the cabin, showcasing the peaceful countryside setting.

Ranch in Paris

5.0 out of 5 average rating, 115 reviews

Peaceful Texas Farm Stay | Fishing & Nature Escape

Rustic Blacksmith-Themed Retreat on a Working Farm Step into a cozy, barn-inspired retreat with a blacksmith shop theme. The main floor bedroom has a queen bed, perfect for couples. The loft offers two twin beds and a half bath. It’s accessible by a slightly steeper staircase which may limit access for some guests. Enjoy the warmth, character, and charm of this one-of-a-kind getaway, surrounded by a peaceful countryside.

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Guest favourite

An outdoor seating area is illuminated by string lights, creating a cozy atmosphere. Several Adirondack chairs surround a fire pit, with a grassy area visible in the background. Potted plants add a touch of greenery among the natural setting.

Home in Caddo

4.81 out of 5 average rating, 72 reviews

Farmhouse nestled in hillside…

Keep it simple at this peaceful and centrally-located home. Newly renovated farmhouse gates on 6 acres, surrounded by trees, 2 houses down from Blue River Valley winery, 9 miles from Choctaw Casino, 15 miles from Lake Texoma. Large 4 bedroom family friendly house can sleep up to 12. Fire pit, 2 outdoor patios with outdoor seating and gas grill. Lyft and Uber only $15 ride from casino.

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Top guest favourite

Guest house in Durant

4.95 out of 5 average rating, 19 reviews

Bakers Run 11 miles from Choctaw Casino

Unwind in the quiet of country life, where peaceful surroundings and open space invite you to slow down and relax. This cozy studio retreat is just 11 miles from Choctaw Casino, offering the perfect blend of convenience and tranquility. Enjoy morning walks, fresh air, and a calm escape from the busy pace of everyday life—ideal for weekend getaways, work stays, or a restful recharge.

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