Bennington Vacation Rentals

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Aug 8 - Aug 9
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Vacation Rentals in Bennington

1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Enjoy serene lakeside views from the porch of this charming lakeside retreat, where you can relax and unwind amidst lush greenery.

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

10.0 out of 10, Exceptional, (193)
"This was the second time we stayed at the cabin. Very peaceful, wonderful views, and only 25 minutes from downtown Madison. Highly recommend! "
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Stoney Creek - Sit back and unwind
Enjoy cooking in this inviting kitchen with a central island, oven, and window overlooking the surrounding landscape.

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (91)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind
The Artist’s A-Frame
Enjoy a view of the surrounding greenery from the large window.

The Artist’s A-Frame

10.0 out of 10, Exceptional, (14)
"Stayed for the weekend to hike at Clifty Falls. Great location to the state park and downtown restaurants. Really pretty house with everything you’d need for a stay. Host was super nice to interact with as well. Thanks again! "
The price is CA $166
CA $327 total
includes taxes & fees
Aug 12 - Aug 13
The Artist’s A-Frame
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Compact kitchen with modern design, featuring an oven, microwave, and window.

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

9.6 out of 10, Exceptional, (50)
"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
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Enjoy cooking and socializing in this kitchen with a central island and bar stools, featuring stainless steel appliances and a pendant light fixture.

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

9.8 out of 10, Exceptional, (35)
"Clean, comfortable home with everything needed for our stay. "
The price is CA $172
CA $341 total
includes taxes & fees
Aug 19 - Aug 20
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Relax in a comfortable living space with a sectional sofa and large mirror.

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

10.0 out of 10, Exceptional, (46)
"Suzy and Ron definitely go above and beyond to make sure your stay is as wonderful as possible. Everything about the property is fantastic. We will definitely be back!"
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Modern kitchen with stainless steel appliances, light grey cabinetry, and a black and white patterned rug.

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

10.0 out of 10, Exceptional, (7)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
The Blue Door Place
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, oven, and sink.

The Blue Door Place

9.8 out of 10, Exceptional, (12)
"Location was close to highway, river and Casino."
The price is CA $110
CA $223 total
includes taxes & fees
Aug 19 - Aug 20
The Blue Door Place
Rustic cabin just outside of Madison!
Relax in a spacious room with a four-poster bed, wooden headboard, and a ceiling fan.

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (41)
"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!
Madison's Only YURT Experience
Exposed wooden beams and a rustic wooden table set the tone in this cozy space with a ladder leading to a higher level.

Madison's Only YURT Experience

9.4 out of 10, Exceptional, (8)
"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
Charming 2-bedroom house in Devil's Elbow Osgood, IN
Smart TV

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."
Charming 2-bedroom house in Devil's Elbow Osgood, IN
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.
Escape to a serene forest setting with a fire pit and seating area.

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

10.0 out of 10, Exceptional, (306)
"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.
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Classic townhouses with porches and gardens line the quiet street.

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
10.0 out of 10, Exceptional, (7)
"Really enjoyed our stay. Super easy to find, plenty of parking. Walking distance of the shops. 10/10 would stay again."
The price is CA $173
CA $231 total
includes taxes & fees
Aug 13 - Aug 14
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
Relax by the pool surrounded by lush greenery, with a table and chairs for dining and unwinding.

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

9.2 out of 10, Wonderful, (29)
"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
"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub
Enjoy cooking in this well-equipped kitchen with a central island, double-door refrigerator, oven, and microwave.

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

10.0 out of 10, Exceptional, (8)
"We thought the house was great and the location was perfect! We would definitely stay there again. "
The price is CA $191
CA $472 total
includes taxes & fees
Aug 10 - Aug 11
"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub
Carol’s Cabin in the Woods in Historic Hoosier Hills
Enjoy a cozy cabin stay with a porch and outdoor seating, perfect for relaxation.

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (35)
"My small group wanted to relax in a quiet setting and Carol’s cabin was perfect. Extremely clean, well-provisioned, quiet and private with a beautiful property to stroll around. Would definitely come back!"
Carol’s Cabin in the Woods in Historic Hoosier Hills
Bungalow on Main!!
Traditional home with a symmetrical facade, featuring a decorative front door and a small porch area.

Bungalow on Main!!

9.8 out of 10, Exceptional, (15)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!
The Wadsworth in National Historic District of Madison, Indiana.
Enjoy cooking in this well-equipped kitchen with an oven and stovetop.

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (51)
"Wonderful VRBO steps away from the Ohio River and historic Madison in a very quiet setting. The home is comfortable, clean and very well-equipped, and the seating at the rear of the house is a nice bonus! The owners are great people, and have anticipated every need for a short or long stay. Highly recommend this property!"
The Wadsworth in National Historic District of Madison, Indiana.
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
Enjoy al fresco dining and socializing in this patio area, featuring a fire pit, bench, and table.

"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit

9.4 out of 10, Exceptional, (8)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
The price is CA $191
CA $472 total
includes taxes & fees
Aug 10 - Aug 11
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Relax on the deck overlooking the river with a soothing hot tub at your fingertips.

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

10.0 out of 10, Exceptional, (45)
"It was perfect for our group of 7. "
The price is CA $263
CA $679 total
includes taxes & fees
Aug 13 - Aug 14
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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Top Bennington Hotel Reviews

Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

10/10 Excellent
"The staff was friendly especially Sheila. The hotel was conveniently off the hwy."
Jacquelynn 1-night trip
Posted 4 days ago
Ramada by Wyndham Sparta/At Speedway

Frequently asked questions

Can I find vacation rentals in Bennington?

Yes, we have vacation rentals close to popular local attractions in Bennington, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Bennington?

The Wee House is a shotgun house that is remodeled with a view of the Ohio river: Visitors like this Bennington vacation home rental. It is located on a river and has a patio, a selection of games, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 larger area.

What’s a vacation rental in Bennington like?

A vacation rental is a private property you can book for short or long periods in Bennington. Vacation rentals feature extras such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.