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, (189)
"Beautiful, stunning views!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

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

9.8 out of 10, Exceptional, (30)
"Clean, comfortable home with everything needed for our stay. "
The price is €217
includes taxes & fees
13 Jul - 14 Jul
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

10.0 out of 10, Exceptional, (3)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (87)
"My husband and our son stayed for two nights and had a great time! The cabin was clean and just overall really nice. The hot tub was fantastic! The owners were very communicative and responsive. Overall, this made for a perfect little getaway!"
Stoney Creek - Sit back and unwind

The Wee House is a shotgun house that is remodeled with a view of the Ohio river

9.6 out of 10, Exceptional, (47)
"We loved the Wee House. It was great at the end of the day to sit on the porch, listen to the birds, and watch the barges on the river. The kitchen had everything we needed. We especially liked the quilts on the beds--so cheerful and colorful. And the location was perfect--just two short blocks from Main Street so we could walk everywhere."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (38)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!

Historic woodside view suite 205, Historic woodside view suite 205

9.0 out of 10, Wonderful, (2)
"This was perfect for my daughter and I for a quick one-day softball tourney. The apartment is extremely clean, easy to find, and comfortable. "
The price is €138
includes taxes & fees
5 Aug - 6 Aug
Historic woodside view suite 205, Historic woodside view suite 205

Grace Woods - Private Lake | Dock | Outdoor Space

Grace Woods - Private Lake | Dock | Outdoor Space

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

Rustic Cabin at Lost Trails

10.0 out of 10, Exceptional, (5)
"It was a great peaceful getaway for my wife and I. Quiet and clean. "
Rustic Cabin at Lost Trails

The Blue Door Place

9.6 out of 10, Exceptional, (10)
"We needed a place for a wedding nearby! The property was very nice, decorated very cute, had all the essentials & was very clean! Would definitely recommend. They even had kids toys & a swing set which was very nice for the kids!! "
The price is €156
includes taxes & fees
21 Jul - 22 Jul
The Blue Door Place

East End River Retreat: Dogs Welcome!

10.0 out of 10, Exceptional, (5)
"We had a lovely time. Great property with easy access to everything. Our kids loved the golf cart and we appreciated the extra touches from the owners. Great little house for a stay in a great little town."
East End River Retreat: Dogs Welcome!

Madison's Only YURT Experience

9.0 out of 10, Wonderful, (6)
"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

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (47)
"We absolutely loved our stay in Madison at the Wadsworth House! You couldn't ask for a nicer place to stay for a quiet get away!"
The Wadsworth in National Historic District of Madison, Indiana.

Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

10.0 out of 10, Exceptional, (303)
"My family and I truly enjoyed our stay. We love coming here it has all the amenities that added to our comfort. Hosts were very accommodating which was really appreciated. "
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

10.0 out of 10, Exceptional, (4)
"Riverside Retreat is a must stay! It is a great location and exactly as described. Highly recommend. We will be back!"
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub

10.0 out of 10, Exceptional, (7)
"We thought the house was great and the location was perfect! We would definitely stay there again. "
The price is €291
includes taxes & fees
9 Jul - 10 Jul
"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub

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

10.0 out of 10, Exceptional, (46)
"Awesome home in a great location! Very well done inside with unique features and lots of room. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

Charming 2-bedroom house in Devil's Elbow Osgood, IN

10.0 out of 10, Exceptional, (1)
"House is as pictured and stated. Beds were comfortable, well stocked kitchen, nice keurig selection of coffee, beautiful outdoor setting behind house backs up to woods,very peaceful. Great place would stay again."
The price is €147
includes taxes & fees
10 Jul - 11 Jul
Charming 2-bedroom house in Devil's Elbow Osgood, IN

Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

10.0 out of 10, Exceptional, (43)
"It was perfect for our group of 7. "
The price is €432
includes taxes & fees
9 Jul - 10 Jul
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
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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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 Vevay Island 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.