Holiday Rentals in Bennington

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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, (180)
"Beautiful, stunning views!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (70)
"Was a beautiful cabin wonderful hot tub awesome views loved the cows "
The price is €220
includes taxes & fees
23 Feb - 24 Feb
Stoney Creek - Sit back and unwind

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

10.0 out of 10, Exceptional, (23)
"This place is awesome! It’s the best place to stay in Madison, IN. Well decorated and has everything you need. The host Suzie goes over and above to make sure your stay is memorable. Great location in town. We already have future dates reserved and will add more in 2025. "
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

9.8 out of 10, Exceptional, (22)
"Had a good time "
The price is €220
includes taxes & fees
19 Feb - 20 Feb
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

9.8 out of 10, Exceptional, (39)
"The space was perfect for 4 of us traveling for a girls’ trip. Location was close to all the shops and restaurants. "
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (32)
"This cabin was off the beaten path and nestled in the woods. Very nice cabin with all the amenities you could ask for. Definitely needed a 4x4 vehicle crossing the stream. It was still full of ice and snow from the recent storm. Will stay again when in the area. "
Rustic cabin just outside of Madison!

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

10.0 out of 10, Exceptional, (42)
"The house is stunning. Very well decorated and completely outfitted for our stay. The kitchen had everything you could need. The owners were easy to communicate with and very helpful. Would highly recommended the property. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

Secluded Country Home in Historic Hoosier Hills

10.0 out of 10, Exceptional, (117)
"This was an excellent place we loved it!"
Secluded Country Home in Historic Hoosier Hills

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

10.0 out of 10, Exceptional, (11)
"This place. This owner. This was far beyond our expectations ! The location is beautiful. Comfortable . Spotless. Safe. There is no stone left unturned in this property. The owner, Suzie, is absolutely lovely. She makes the stay so comfortable and makes sure that you know where everything is . The town is fantastic and we had the time of our lives. Already looking forward for our next trip ! Thank you !!"
Livery Loft: our other BEST downtown location! Award winning! Come see why.

#207 King Suites, River Views, Deck, Downtown

10.0 out of 10, Exceptional, (29)
"We had a 5 couples get away for one evening and stayed in the house. A great view of the river and perfect location for walks to the shops, Park and restaurants. We plan on staying here again in the future! "
The price is €519
includes taxes & fees
19 Feb - 20 Feb
#207 King Suites, River Views, Deck, Downtown

The Artist’s A-Frame

10.0 out of 10, Exceptional, (10)
"We were a group of three longtime friends in town for a holiday weekend together. The Artist’s A-Frame was the perfect place to retire at the end of a great day of shopping and eating. The home was clean, cozy, and well-appointed, and it was located in a lovely neighborhood. The owners were very responsive and easy to work with. Highly recommend the A-Frane! "
The price is €229
includes taxes & fees
2 Mar - 3 Mar
The Artist’s A-Frame

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

9.0 out of 10, Wonderful, (16)
"Had a nice relaxing time"
Peaceful getaway centrally located just min. from Madison and Belterra casino.

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

10.0 out of 10, Exceptional, (288)
"This was our second time to stay at Sonshine Cabin. It is very clean! Decorated super cute and the kitchen is well appointed. Owners are great with communication, as well. We will definitely come again."
Sonshine Cabin a great place to enjoy the Holidays with family or friends

SKY Parlor sunrise and sunset views overlooking the river

9.4 out of 10, Exceptional, (6)
"Was a nice view of the riverThe parking was sketchy. Also would've been nice to know we were renting the attic in an A Frame home. "
The price is €164
includes taxes & fees
19 Feb - 20 Feb
SKY Parlor sunrise and sunset views overlooking the river

Bungalow on Main!!

9.6 out of 10, Exceptional, (7)
"Place was clean, downtown, and what pictures shown. Owner was kind and understanding. "
Bungalow on Main!!

#209 Kings, River View, Deck, Bicentennial Park

10.0 out of 10, Exceptional, (55)
"Nice property and well equipped. We had no problem cooking full breakfast and full dinner for 8 people. Nice location for walking to places in town."
The price is €519
includes taxes & fees
19 Feb - 20 Feb
#209 Kings, River View, Deck, Bicentennial Park

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

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (29)
"We wanted to get away for a bit and we hit the jackpot with this place! It was very clean, well stocked and a beautiful property. You can definitely tell that the property is well kept and maintained. We loved hiking the trails with our dogs. The scenery is beautiful! If you want a peaceful, relaxing experience to unplug and enjoy God’s creation, or quality time, this is your place! We definitely will return to in the future!"
Carol’s Cabin in the Woods in Historic Hoosier Hills

Madison's Only YURT Experience

9.0 out of 10, Wonderful, (4)
"Better than we expected! Lots of land for the kids to explore. The goats were so fun to watch. Fishing at the pond was a nice surprise. We loved the bottle of wine waiting for us! It was such a unique getaway! Great family trip!"
Madison's Only YURT Experience

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

9.4 out of 10, Exceptional, (15)
"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
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, (1004)
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The price is €165
includes taxes & fees
25 Feb - 26 Feb
Belterra Casino Resort

Best Way Inn Madison

2.5 star property
6.8 out of 10, (466)
"Reasonable price/location for overnight trip to Madison, IN."
The price is €61
includes taxes & fees
19 Feb - 20 Feb
Best Way Inn Madison

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

2.5 star property
9.8 out of 10, Exceptional, (300)
"Fabulous hotel. Spacious rooms. Friendly staff. Madison is a great area to shop, eat and just walk around. "
The price is €171
includes taxes & fees
2 Mar - 3 Mar
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill
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.

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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: This holiday home rental outside of Bennington offers a patio, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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. The Ridge Winery Tasting Room and Belterra Casino 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.