Holiday rentals in Bennington

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.

Value · Location · Checkout

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.

Location · Family · Nearby

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!

Value · Location · View

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.

Location · Family · Nearby

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)

Value · Family · Check-in

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.

Location · Value · Comfort

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.

Family · Location · Outdoor spaces

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.

Family · Location · Parking

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.

Family · Location · Amenities

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.

Family · Value · Decor

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.

Family · Value · Quiet

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.

Family · Value · View