Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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

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Top guest favorite
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, 288 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.

Top guest favorite
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
4.99 out of 5 average rating, 129 reviews

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)

Guest favorite
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
4.89 out of 5 average rating, 105 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.

Superhost
A rectangular firepit area is surrounded by wooden logs, with flames gently rising from the center. Soft gray gravel covers the ground, and a grassy landscape extends in the background under a twilight sky, hinting at the transition from day to night.
Cabin in Bokchito
4.86 out of 5 average rating, 21 reviews

RED FOX RANCH 15 miles/Choctaw Casino 160 acres

Cabin for two located less than 20 minutes to the Choctaw Casino in Durant, Oklahoma and just over an hour from the Dallas area. The property sits on a large 160 acre gated ranch with a 2 acre fishing pond stocked with bass and crappie. Groomed hiking trails throughout and large firepit for your enjoyment. Beautiful property where you can relax and enjoy nature, yet close to entertainment and restaurants. Very clean and comfortable cabin. Lots of wildlife to see and plenty of outdoor fun.

Top guest favorite
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
5 out of 5 average rating, 43 reviews

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.

Top guest favorite
A spacious living area is highlighted by a comfortable brown sofa and a sleek round coffee table. Natural light fills the space, accentuating the warm wood accents and modern design. A staircase with a wooden railing leads to an upper level, providing additional visual interest.
Home in Durant
5 out of 5 average rating, 36 reviews

AirbnP: Luxury Pickleball Barndo- Choctaw Casino

Step into your luxury barndominium with your very own indoor, professional pickleball court! AirbnP is conveniently located 3 miles from the Choctaw Casino & Resort, and 15 minutes from the beautiful Lake Texoma! Amenities Include: - Indoor Pickleball Court - Exercise Equipment - Wi-Fi - Roku TV - Bathroom Necessities - Coffee Bar - Children’s playroom/toys -AIR MATTRESS FOR ADDITIONAL GUESTS (1-2) Special Amenities: - Alexapure Gravity Water Purifier - Homedics Sound Machine

Top guest favorite
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 out of 5 average rating, 25 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.

Top guest favorite
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 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.

Top guest favorite
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, 696 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.

Top guest favorite
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, 259 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.

Guest favorite
Home in Durant
4.78 out of 5 average rating, 9 reviews

The Restful Retreat close to all attractions

Our guests will enjoy easy access to everything from this centrally located retreat while still being able to unwind and relax in a peaceful setting only 3 minutes off of Hwy 69/75. Enjoy a beautiful private backyard with a fire pit, hammocks and outdoor dining. We are just minutes from shopping and restaurants in Durant and only 7 miles from Choctaw casino.

Top guest favorite
Home in Caddo
5 out of 5 average rating, 39 reviews

Nana’s house

This quiet and peaceful place is tucked away on the edge of town off the old Jefferson Highway. It is centrally located near several places to eat and visit. Reba’s Place in Atoka and Choctaw Casino and Resorts in Durant are both within 20 minutes. Ole Reds in Tishomingo is a 40 minute drive. Lake Texoma and McGee Creek are also within 40 minutes.

Popular amenities for Bennington vacation rentals

  1. Airbnb
  2. United States
  3. Oklahoma
  4. Bryan County
  5. Bennington