Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Bennington vacation rentals

Fridge, microwave, oven, stovetop

Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly

Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly
Warsaw
8.0 out of 10, Very Good, (9 reviews)
"We certainly enjoyed the great view. Beautiful‼Fully furnished with lots of options. And our hosts were instantly responsive to our questions. Checkin and out were flawless "
United States
Gene M.
The price is ￥22,536
￥63,724 total
includes taxes & fees
Mar 30 - Mar 31
Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly
Smart TV, fireplace, books, music library

Riverside Storybook Cottage

Riverside Storybook Cottage
Aurora
10.0 out of 10, Exceptional, (4 reviews)
"Great time and place!!!"
United States
Brad T.
The price is ￥43,909
￥92,422 total
includes taxes & fees
Apr 4 - Apr 5
Riverside Storybook Cottage
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, (55 reviews)
"My family had a wonderful stay and the host was very responsive and accommodating. Very comfortable rooms and a beautiful view. "
United States
Ashlee B.
The price is ￥33,349
￥82,955 total
includes taxes & fees
Apr 5 - Apr 6
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
9.8 out of 10, Exceptional, (10 reviews)
"Wonderful vacation home. Very clean, great host that was very helpful. "
United States
Ashley C.
The price is ￥28,279
￥63,462 total
includes taxes & fees
Mar 31 - Apr 1
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
Dining

The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (21 reviews)
"Very clean and comfortable, secluded location made for a very peaceful evening around the firepit"
United States
Gage G.
The price is ￥15,149
￥28,639 total
includes taxes & fees
Mar 31 - Apr 1
The Blue Door Place
Interior

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Madison
9.6 out of 10, Exceptional, (21 reviews)
"My wife and I enjoyed our stay here while checking out Madison. Great location, nicely decorated. "
United States
Justin L.
The price is ￥28,856
￥46,458 total
includes taxes & fees
Mar 30 - Mar 31
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
TV, fireplace, DVD player

Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (17 reviews)
"Nice cabin"
United States
Nathan M.
The price is ￥22,764
￥43,692 total
includes taxes & fees
Apr 5 - Apr 6
Cabin on the Ridge
Exterior

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful place to stay "
United States
Susan H.
The price is ￥19,398
￥37,978 total
includes taxes & fees
Apr 12 - Apr 13
The Artist’s A-Frame
Pool

#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison
10.0 out of 10, Exceptional, (63 reviews)
"Great house, great location and the host was very responsive! I would definitely recommend this place. "
United States
Lisa C.
The price is ￥30,299
￥67,141 total
includes taxes & fees
Mar 30 - Mar 31
#209 Kings, River View, Deck, Bicentennial Park
Property grounds

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

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.0 out of 10, Wonderful, (4 reviews)
"Welcoming host and cottage as described. Thanks! "
United States
Adam H.
The price is ￥14,284
￥27,489 total
includes taxes & fees
Mar 30 - Mar 31
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior

Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (9 reviews)
"Very nice place definitely recommend "
United States
Eric T.
The price is ￥13,626
￥24,968 total
includes taxes & fees
Apr 2 - Apr 3
Maple Cozy Cabin at Lost Trails
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, (58 reviews)
"Nice friendly town and eating places"
United States
Paul P.
The price is ￥16,833
￥35,581 total
includes taxes & fees
Apr 5 - Apr 6
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
1 bedroom, WiFi, bed sheets

East Main Lofts - Boho 203

East Main Lofts - Boho 203
Madison
9.6 out of 10, Exceptional, (8 reviews)
"I didn’t receive check in information and had to text several times to get information that I should have received. The unit was nice but basically just a big hotel room. Location is great. "
United States
Leann L.
The price is ￥45,850
￥74,297 total
includes taxes & fees
Mar 30 - Mar 31
East Main Lofts - Boho 203
Pool

#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison
10.0 out of 10, Exceptional, (38 reviews)
"Great Amenities! The layout was perfect and the house was well stocked. Kitchen and bathrooms had everything we needed. Great location. Minutes away from restaurants and shops. "
United States
Michele D.
The price is ￥30,299
￥67,695 total
includes taxes & fees
Apr 5 - Apr 6
#207 King Suites, River Views, Deck, Downtown
Interior

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison
The price is ￥13,707
￥26,825 total
includes taxes & fees
Mar 30 - Mar 31
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Terrace/patio

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison
10.0 out of 10, Exceptional, (15 reviews)
"Great location and the host thought of everything to stock the house with."
United States
Kinni L.
The price is ￥22,955
￥60,689 total
includes taxes & fees
Apr 14 - Apr 15
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Exterior detail

The Madison Inn, Southern view on Main suite 202, Southern view on Main suite 202

The Madison Inn, Southern view on Main suite 202, Southern view on Main suite 202
Madison
9.4 out of 10, Exceptional, (3 reviews)
"The studio was quaint and well appointed. Great location! The host was very accommodating. We look forward to a return stay."
United States
Thomas V.
The price is ￥17,474
￥27,194 total
includes taxes & fees
Apr 12 - Apr 13
The Madison Inn, Southern view on Main suite 202, Southern view on Main suite 202
Terrace/patio

Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is ￥15,390
￥26,996 total
includes taxes & fees
Mar 30 - Mar 31
Walnut Secluded Cabin at Lost Trails
Exterior

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (9 reviews)
"The amenities were in excellent condition and great layout of the property. "
United States
Ed S.
The price is ￥14,107
￥25,521 total
includes taxes & fees
Apr 8 - Apr 9
Sassafras Woodland Cabin at Lost Trails
TV, fireplace

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is ￥22,764
￥41,111 total
includes taxes & fees
Apr 6 - Apr 7
Cabin on the Ridge: The Sequel
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

Hillside Inn

Hillside Inn

8/10 Good
"Breakfast leaves a lot to be desired (wet eggs, floppy over-thin bacon), but otherwise, it’s a great view, friendly and professional staff, clean room, comfortable stay. "
Craig 2-night trip
Posted 3 hours ago
Hillside Inn

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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: Visitors like this Bennington vacation home rental. It 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?

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. Belterra Casino and Belterra Casino Riverboat 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.