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Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

Our top choices for Bennington vacation rentals

Interior

604 GQ on Mulberry: 2 King Luxury Suites, Patio

604 GQ on Mulberry: 2 King Luxury Suites, Patio
Madison
604 GQ on Mulberry: 2 King Luxury Suites, Patio
TV, fireplace, DVD player

Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is ￥22,959
￥43,137 total
includes taxes & fees
Aug 2 - Aug 3
Cabin on the Ridge
Interior

2 Queen Beds|Non Smoking

2 Queen Beds|Non Smoking
Aurora, IN
10.0 out of 10, Exceptional, (76 reviews)
"Peaceful stay with friendly staff!"
United States
Anonymous traveler
The price is ￥13,086
￥14,657 total
includes taxes & fees
Jul 19 - Jul 20
2 Queen Beds|Non Smoking
Dining

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

Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Aurora
10.0 out of 10, Exceptional, (58 reviews)
"Happy with our stay and house "
United States
Manda C.
The price is ￥34,748
￥84,369 total
includes taxes & fees
Jul 13 - Jul 14
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Exterior

Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway

Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
Sparta
9.6 out of 10, Exceptional, (14 reviews)
"This was a very nice location. The home was comfortable and nice. "
United States
Seth and Katie S.
The price is ￥28,520
￥64,004 total
includes taxes & fees
Jul 17 - Jul 18
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
Exterior

Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is ￥16,168
￥27,971 total
includes taxes & fees
Aug 3 - Aug 4
Maple Cozy Cabin at Lost Trails
Smart TV, fireplace, video games, foosball

Waterfront Cabin | Near ARK | Large Family Retreat

Waterfront Cabin | Near ARK | Large Family Retreat
Warsaw
8.0 out of 10, Very Good, (10 reviews)
"Great host. Great home and an excellent stay highly recommended "
United States
Chris A.
The price is ￥32,270
￥87,274 total
includes taxes & fees
Jul 15 - Jul 16
Waterfront Cabin | Near ARK | Large Family Retreat
TV, fireplace

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is ￥21,827
￥40,347 total
includes taxes & fees
Jul 13 - Jul 14
Cabin on the Ridge: The Sequel
Pool

#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison
10.0 out of 10, Exceptional, (70 reviews)
"Couldnt recommend more! Great place and hosts!"
United States
Zach D.
The price is ￥30,558
￥67,901 total
includes taxes & fees
Jul 14 - Jul 15
#209 Kings, River View, Deck, Bicentennial Park
Exterior detail

Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (28 reviews)
"Peaceful and quiet loved it "
United States
Robert V.
The price is ￥17,785
￥30,016 total
includes taxes & fees
Jul 13 - Jul 14
Cedar Rustic Cabin at Lost Trails
Terrace/patio

Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is ￥16,168
￥27,971 total
includes taxes & fees
Jul 19 - Jul 20
Walnut Secluded Cabin at Lost Trails
Dining

The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (25 reviews)
"Very clean, had everything we needed! "
United States
james w.
The price is ￥15,279
￥28,884 total
includes taxes & fees
Jul 12 - Jul 13
The Blue Door Place
Smart TV

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

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (68 reviews)
"We were very pleased with the location and cleanliness of the home. Comfy and cozy atmosphere and communication with owner was great! Highly recommend for a nice quiet getaway! "
United States
Julie L.
The price is ￥20,210
￥40,347 total
includes taxes & fees
Jul 22 - Jul 23
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior

Buggy Shed

Buggy Shed
Versailles
10.0 out of 10, Exceptional, (1 review)
"Clean, pet friendly, and near the 2 state parks we wanted to see. Easy to check in and host was quick to communicate with us! We stayed at the school house and it was nice!"
United States
Ron L.
The price is ￥25,085
￥31,717 total
includes taxes & fees
Jul 19 - Jul 20
Buggy Shed
Property grounds

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (12 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is ￥18,043
￥32,277 total
includes taxes & fees
Jul 13 - Jul 14
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (36 reviews)
"Everything was absolutely wonderful "
United States
Michael (alex) W.
The price is ￥19,563
￥38,674 total
includes taxes & fees
Jul 29 - Jul 30
The Artist’s A-Frame
Exterior

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison
The price is ￥18,917
￥39,418 total
includes taxes & fees
Jul 12 - Jul 13
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Interior

Cozy River View 1BR Near Creation Museum+ Perfect North Slopes

Cozy River View 1BR Near Creation Museum+ Perfect North Slopes
Aurora
The price is ￥21,099
￥36,851 total
includes taxes & fees
Jul 12 - Jul 13
Cozy River View 1BR Near Creation Museum+ Perfect North Slopes
Private kitchen

Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (2 reviews)
"This tiny home was exactly what we had expected. Very clean, nice and welcoming. The owners were great and communication was excellent. We will be sure to see if it is Ava when we come to visit family again. "
United States
Randall B.
The price is ￥14,228
￥31,508 total
includes taxes & fees
Jul 22 - Jul 23
Charming new tiny house-Friendship IN
Exterior

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"We had a wonderful stay! Everything was clean, communication was great - it was the perfect weekend getaway!"
United Kingdom
Karen L.
The price is ￥16,168
￥27,971 total
includes taxes & fees
Jul 22 - Jul 23
Sassafras Woodland Cabin at Lost Trails
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

Quality Inn Carrollton

Quality Inn Carrollton

10/10 Excellent
"Great breakfast, very clean. Staff is friendly "
Sotero 1-night trip
Posted 1 hour ago
Quality Inn Carrollton

Find out more about Bennington

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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?

Unique! Edgar Allan Poe inspired Gothic themed home in Madison: Visitors like this Bennington vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Bennington?

Explore the area and family-friendly sights such as Madison Railroad Station Museum, or get out into nature at a spot like General Butler State Resort Park. 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.