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Bennington Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Bennington holiday rentals

A wooden deck with two wicker chairs and a small table, a potted plant with yellow flowers, and a door with a keypad lock.

1. Tiny Farm home on 225 acres. 28 miles from Durant Casino & resort. Pet friendly!

Tiny Farm home on 225 acres. 28 miles from Durant Casino & resort. Pet friendly!
Bennington
10.0 out of 10, Exceptional, (10 reviews)
"Had a mom’s getaway weekend and this was perfect! Quiet and serene. Would definitely book again! "
United States
Ashleigh S.
The price is HK$953
HK$1,814 total
includes taxes & fees
27 Oct - 28 Oct
Tiny Farm home on 225 acres. 28 miles from Durant Casino & resort. Pet friendly!
An outdoor deck with a table and chairs, surrounded by trees.

2. Riverside Rest - 27 miles from Durant - King Bed- horse lot on property

Riverside Rest - 27 miles from Durant - King Bed- horse lot on property
Bennington
10.0 out of 10, Exceptional, (5 reviews)
"This is one of the best places to stay for a weekend getaway with the creek flowing behind the home and the deck is awesome with all the night lighting "
United States
Vamshi V.
The price is HK$1,165
HK$2,068 total
includes taxes & fees
27 Oct - 28 Oct
Riverside Rest - 27 miles from Durant - King Bed- horse lot on property
A building with a red door, a hanging wreath, and two rocking chairs on the porch.

3. Modern Barn Apartment

Modern Barn Apartment
Durant
10.0 out of 10, Exceptional, (149 reviews)
"This is a lovely property with lovely hosts. You will be well taken care of during your stay."
United States
Christina C.
The price is HK$882
HK$1,526 total
includes taxes & fees
27 Oct - 28 Oct
Modern Barn Apartment
A wooden cabin with a green roof, a porch with a railing, and two metal chairs in front.

4. Cabin for two on 160 Acres,less than 20 min from Choctaw Casino Durant OK

Cabin for two on 160 Acres,less than 20 min from Choctaw Casino Durant OK
Bokchito
9.6 out of 10, Exceptional, (16 reviews)
"My husband is a FedEx exec that needed some time away from computer time and just some relaxation and family time and I hat was just what we got!!! Amazing to be out of the city. See real stars and roast s’mores and weeinies!!!!"
United States
Amy S.
The price is HK$1,529
HK$2,269 total
includes taxes & fees
27 Oct - 28 Oct
Cabin for two on 160 Acres,less than 20 min from Choctaw Casino Durant OK
A living room with a brown leather sofa, a brown recliner, a television on a stand, a dining table with chairs, and a window with curtains.

5. Nana's house

Nana's house
Caddo
10.0 out of 10, Exceptional, (9 reviews)
"Excellent property and host."
United States
Teresa W.
The price is HK$949
HK$1,405 total
includes taxes & fees
27 Oct - 28 Oct
Nana's house
A small cabin with a porch, two blue chairs, a Christmas sign, and a door with a star decoration.

6. The Cool Blue Cabin

The Cool Blue Cabin
Caney
The price is HK$784
HK$1,449 total
includes taxes & fees
6 Nov - 7 Nov
The Cool Blue Cabin
A bathroom with a rustic wooden sink, a mirror with a woven frame, and a window with a view of the outside.

7. Camping in comfort in the woods of North Texas

Camping in comfort in the woods of North Texas
Honey Grove
The price is HK$596
HK$802 total
includes taxes & fees
2 Nov - 3 Nov
Camping in comfort in the woods of North Texas
A cozy room with wooden walls, a bed with a gray bedspread, and a small table with a clock.

8. Cozy little cabin in a small town

Cozy little cabin in a small town
Caney
10.0 out of 10, Exceptional, (5 reviews)
"We loved it and will come back"
United States
Kassie K.
The price is HK$549
HK$1,178 total
includes taxes & fees
29 Oct - 30 Oct
Cozy little cabin in a small town
An outdoor seating area with wicker chairs, a round table, and a floral-patterned rug.

9. Reconnect with nature at this unforgettable escape.

Reconnect with nature at this unforgettable escape.
Honey Grove
The price is HK$784
HK$1,523 total
includes taxes & fees
26 Nov - 27 Nov
Reconnect with nature at this unforgettable escape.
A forested outdoor area with wicker chairs, a small table, and a potted plant.

10. Charming Vintage Trailer with Colorful 50s Décor near Honey Grove, Texas

Charming Vintage Trailer with Colorful 50s Décor near Honey Grove, Texas
Honey Grove
The price is HK$1,430
HK$1,715 total
includes taxes & fees
27 Oct - 28 Oct
Charming Vintage Trailer with Colorful 50s Décor near Honey Grove, Texas
A kitchen with white cabinets, stainless steel appliances, a microwave, a stove, and a sink.

11. 3BR●Private Bath Sweets●Game Room●Casino Nearby

3BR●Private Bath Sweets●Game Room●Casino Nearby
Durant
10.0 out of 10, Exceptional, (15 reviews)
"This had to be one of the cleanest homes I’ve ever stayed in very nice if available we will definitely stay here again next time we go to the casino"
United States
Shawna M.
The price is HK$1,200
HK$3,024 total
includes taxes & fees
27 Oct - 28 Oct
3BR●Private Bath Sweets●Game Room●Casino Nearby
A yellow bedside table with a small potted plant and a framed sign that says "BEE happy".

12. 3-bedroom house in marvelous Calera with WiFi, AC

3-bedroom house in marvelous Calera with WiFi, AC
Calera
10.0 out of 10, Exceptional, (6 reviews)
"Check-in was very smooth, and the place was super clean! There were nice personal touches to make our stay comfortable, even though we were only there one night. Would stay again. "
United States
Kassie K.
The price is HK$1,216
HK$1,543 total
includes taxes & fees
27 Oct - 28 Oct
3-bedroom house in marvelous Calera with WiFi, AC
A bedroom with a large bed, two bedside lamps, and a decorative headboard.

13. Rodeo Ranch 55 acres, 3 BDR, Pool, Parking, located close to Casino

Rodeo Ranch 55 acres, 3 BDR, Pool, Parking, located close to Casino
Durant
9.8 out of 10, Exceptional, (100 reviews)
"We love staying here - very clean; close to the casino; swimming pool; lots of space."
United States
laura r.
The price is HK$1,451
HK$2,847 total
includes taxes & fees
27 Oct - 28 Oct
Rodeo Ranch 55 acres, 3 BDR, Pool, Parking, located close to Casino
A cozy wooden cabin room with a bed, a TV, a bench, and a TV stand.

14. NEW Bloom Cottage-Cozy Country Retreat

NEW Bloom Cottage-Cozy Country Retreat
Arthur City
10.0 out of 10, Exceptional, (4 reviews)
"We had a blast! The cottage was amazing and everything you could ask for!"
United States
Megan M.
The price is HK$886
HK$1,676 total
includes taxes & fees
27 Oct - 28 Oct
NEW Bloom Cottage-Cozy Country Retreat
Terrace/patio

15. Cozy Bell Tent Retreat with Oak Bar Deck near Nature Trails, Honey Grove, TX

Cozy Bell Tent Retreat with Oak Bar Deck near Nature Trails, Honey Grove, TX
Honey Grove
Cozy Bell Tent Retreat with Oak Bar Deck near Nature Trails, Honey Grove, TX
A two-story house with a stone-paved front porch, white railings, and a small garden area.

16. Cute and cozy cottage in Atoka, home of Reba’s Place.

Cute and cozy cottage in Atoka, home of Reba’s Place.
Atoka
10.0 out of 10, Exceptional, (23 reviews)
"Very cute place and comfy beds. "
United States
Tawnya R.
Cute and cozy cottage in Atoka, home of Reba’s Place.
A spacious kitchen with wooden cabinets, a granite countertop, and a dining area with a long table and chairs.

17. Durant 4BDR house/56 acres less than a 1/2 mile/Choctaw Casino

Durant 4BDR house/56 acres less than a 1/2 mile/Choctaw Casino
Durant
9.2 out of 10, Wonderful, (87 reviews)
"Had a great time - very close to the casino."
United States
Chad B.
The price is HK$1,490
HK$2,944 total
includes taxes & fees
1 Nov - 2 Nov
Durant 4BDR house/56 acres less than a 1/2 mile/Choctaw Casino
Outdoor dining

18. Luxurious Remodeled Airstream with Wraparound Deck and Spa near Honey Grove, Texas

Luxurious Remodeled Airstream with Wraparound Deck and Spa near Honey Grove, Texas
Honey Grove
Luxurious Remodeled Airstream with Wraparound Deck and Spa near Honey Grove, Texas
A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a window with blinds.

19. 10 min to Casino, 2b/1b cozy new home in 2025

10 min to Casino, 2b/1b cozy new home in 2025
Durant
10.0 out of 10, Exceptional, (13 reviews)
"Pet friendly, clean and had what we needed "
United States
Michele C.
The price is HK$925
HK$1,834 total
includes taxes & fees
27 Oct - 28 Oct
10 min to Casino, 2b/1b cozy new home in 2025
A modern, well-lit room with a large bed, a desk, and a dining area.

20. 10 min to Casino, brand new 2b/1b single home 2025

10 min to Casino, brand new 2b/1b single home 2025
Durant
10.0 out of 10, Exceptional, (7 reviews)
"Wonderful stay, had all the amenities we needed! "
United States
Burton B.
10 min to Casino, brand new 2b/1b single home 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Bennington Hotel Reviews

3BR●Private Bath Sweets●Game Room●Casino Nearby

3BR●Private Bath Sweets●Game Room●Casino Nearby

10/10 Excellent
"Close to SE campus, very user friendly, comfortable for our group of 7."
Claudia L. 2-night trip
Posted 5 hours ago
3BR●Private Bath Sweets●Game Room●Casino Nearby

Find out more about Bennington

Search for holiday rentals in Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bennington using one of the methods below:

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Look no further and take a look at our great range of rental properties in Bennington!

Frequently asked questions

Can I find holiday rentals in Bennington?

Yes, there are holiday rentals close to the most popular sights in Bennington, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Bennington has to offer?

Spacious 4-bedroom house in Durant: This holiday home rental outside of Bennington offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What can I see and do in Bennington?

While exploring the area, visit the sights like Red River, Bloomer Sullivan Arena and Southeastern Oklahoma State University. In the wider area, you’ll find Boswell State Park and First Baptist Church of Durant.

What are holiday rentals like in Bennington?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Bennington. Holiday rentals offer extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.