Bennington Holiday Rentals

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Holiday Rentals in Bennington

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (173)
"If you like a different kind of rental, rather remote, picturesque, quiet and private, this may be for you. 1800's cabin atmosphere with enough modern amenities to be very comfortable. A good "get away from it all" place."
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Peaceful getaway centrally located just min. from Madison and Belterra casino.

8.6 out of 10, Excellent, (12)
"Nice, quiet neighborhood in between Vevay and Madison."
Peaceful getaway centrally located just min. from Madison and Belterra casino.

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (26)
"Property and owner are great. Great stay (our 2nd time here). "
Carol’s Cabin in the Woods in Historic Hoosier Hills

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (28)
"It was a nice cabin that is away from people so privacy is good. "
Rustic cabin just outside of Madison!

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (34)
"We had an amazing time in Madison! The home was spotless and had everything you will need plus more! Mona checks in to be sure everything is fine and suggested things to do. You will love the location! Will be my place to stay at all upcoming visits! "
The Wadsworth in National Historic District of Madison, Indiana.

Cozy Cabin Madison Indiana

10.0 out of 10, Exceptional, (13)
"The cabin was great! It was clean and very well maintained! We loved the outdoor space and the location. Close to town, but out far enough that we could enjoy the quiet and the stars at night. The only thing we found challenging was the shower set up. Quite a step up to get in and the shower curtain was a little long and a little bit of a hazard. Otherwise we had everything we needed and we were very comfortable."
Cozy Cabin Madison Indiana

Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River

10.0 out of 10, Exceptional, (206)
"The house was very clean and decorated nicely. Beautiful old river town. Wifi was spotty. This was only an issue in the evening when we wanted to watch a movie. That's my only complaint and for sure not a deal breaker. Great property. Would stay here again!"
Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River

Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 13

9.8 out of 10, Exceptional, (35)
"Close to so many things to do! Perfect weekend getaway location. You won’t regret staying here!"
The price is AU$819
includes taxes & fees
1 Dec - 2 Dec
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 13

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

10.0 out of 10, Exceptional, (19)
"My twin sister and I visited for a birthday trip. Looked just like in the pictures and beds were very comfortable. Kitchen was fully stocked with cooking utensils, pans, salt and pepper, etc. Suzie thought of everything I didn't know we needed or wanted...from a cute birthday banner and piece of cake to milk or cream in the fridge for coffee. Will definitely stay again! Thanks for the hospitality. "
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Rustic Private Cabin on 30 acres w/Loft/Firepit/Secluded/Trails

9.8 out of 10, Exceptional, (32)
"So relaxing and had everything we needed "
Rustic Private Cabin on 30 acres w/Loft/Firepit/Secluded/Trails

KY log home close to The Ark Encounter on private 14 acres private seasonal pool

9.2 out of 10, Wonderful, (26)
"We enjoyed the space the cabin had to offer and had a great time."
KY log home close to The Ark Encounter on private 14 acres private seasonal pool

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (66)
"We loved this cabin. Everything was perfect. We'll definitely be coming back!"
Stoney Creek - Sit back and unwind

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

9.6 out of 10, Exceptional, (13)
"Very nice home with lots of space and great location to many shops."
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

The Blue Door Place

10.0 out of 10, Exceptional, (5)
"The place is adorable and very comfortable. Things we especially appreciated were the super cute and tasteful decor, the fully stocked coffee bar (including travel cups & lids!), the front & back porch areas, location (lovely wooded winding drive leading to the property), and the FAST response from the host any time we had a question. I should also add the place was spotless. We fully enjoyed our stay and would not hesitate to come back!"
The price is AU$288
includes taxes & fees
8 Dec - 9 Dec
The Blue Door Place

Sonshine Cabin a great place to enjoy the Holidays with family or friends

10.0 out of 10, Exceptional, (283)
"We have been blessed this year to see Sonshine in all 4 seasons! Each season offers a different kind of beauty, its too hard to pick our favorite. But it doesn't really matter because we adore this cabin. Its so cozy, clean and inviting. The land surrounding it is so beautiful. We look forward to doing it all over again!"
Sonshine Cabin a great place to enjoy the Holidays with family or friends

Waterfront - Near Ark Encounter

9.4 out of 10, Exceptional, (36)
"We enjoyed our stay here. The house is comfortable and tastefully decorated. Quiet neighborhood. My husband and daughter had a blast fishing. They caught and released at least a dozen catfish a piece. The walk down to the river pier is steep. Not something someone with mobility issues could do. We would stay again. "
Waterfront - Near Ark Encounter

Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

10.0 out of 10, Exceptional, (40)
"This is a beautiful house and very well equipped. Alert - all the bedrooms are on the 2nd floor with is up 25 steps - straight up! The 2 bathrooms on the 2nd floor are not connected to any of the bedrooms and are right next to each other. So - unusual. Wonderful location- easy party - comfortable beds. We did put some of the breakable decorations in a safer place because of our little ones. We enjoyed our stay and would recommend this home. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

#207 King Suites, River Views, Deck, Downtown

10.0 out of 10, Exceptional, (27)
"Great location! Fabulous place to stay! Very clean with comforts of home. Walked to all our destinations during our 3 day visit."
The price is AU$898
includes taxes & fees
1 Dec - 2 Dec
#207 King Suites, River Views, Deck, Downtown

Livery Loft: our other BEST downtown location! Award winning! Come see why.

10.0 out of 10, Exceptional, (9)
"We really enjoyed our stay at Liverly Loft. Even though it rained, we had plenty things to do to keep us busy. This was one of the best VRBO I have ever stayed. Definitely will be back again... "
Livery Loft: our other BEST downtown location! Award winning! Come see why.

Secluded Country Home in Historic Hoosier Hills

10.0 out of 10, Exceptional, (115)
"Great property, very peaceful. "
Secluded Country Home in Historic Hoosier Hills
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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Other types of properties in Bennington you may be interested in

Belterra Casino Resort

3.5 star property
8.4 out of 10, Very good, (1082)
"We had a really fun time!"
The price is AU$210
includes taxes & fees
2 Dec - 3 Dec
Belterra Casino Resort

Best Way Inn Madison

2.5 star property
6.8 out of 10, (450)
"Our TV was broken on arrival and they immediately replaced it even though it was getting late. Great attitudes of the staff."
The price is AU$119
includes taxes & fees
28 Nov - 29 Nov
Best Way Inn Madison

Ramada by Wyndham Sparta/At Speedway

2.5 star property
7.8 out of 10, Good, (1051)
"This was the first time in many years the hotel did not put the breakfast out early for the hunters. I have chosen to stay at the Sparta Ramada because they have made that single concession every other year. I and my other hunting friends that have stayed here for years may look elsewhere in the future. The staff was friendly and have been around for years. "
The price is AU$103
includes taxes & fees
28 Nov - 29 Nov
Ramada by Wyndham Sparta/At Speedway
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Peaceful getaway centrally located just min. from Madison and Belterra casino.: This holiday home rental outside of Bennington is located in a rural location, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

What’s there to see and do in Bennington?

While you're exploring the area, General Butler State Resort Park and Versailles State Park are a couple of picturesque spots to get outside and enjoy nature. Belterra Casino and Historic District are a couple of places you'll find in the wider area.

What’s a holiday rental in Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bennington. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.