Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Bennington vacation rentals

Dining

The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (21 reviews)
"Very clean, had everything we needed! "
United States
james w.
The price is ￥15,026
￥28,406 total
includes taxes & fees
May 24 - May 25
The Blue Door Place
TV, fireplace, DVD player

Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Nice cabin"
United States
Nathan M.
The price is ￥19,261
￥38,442 total
includes taxes & fees
May 26 - May 27
Cabin on the Ridge
Terrace/patio

Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (5 reviews)
"Was a great space! Clean, modern and very cute! Would highly recommend "
United States
Anna M.
The price is ￥15,918
￥27,538 total
includes taxes & fees
May 31 - Jun 1
Walnut Secluded Cabin at Lost Trails
Exterior

Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Very nice place definitely recommend "
United States
Eric T.
Maple Cozy 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 ￥22,578
￥40,776 total
includes taxes & fees
Jun 8 - Jun 9
Cabin on the Ridge: The Sequel
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, (12 reviews)
"Wonderful vacation home. Very clean, great host that was very helpful. "
United States
Ashley C.
The price is ￥28,048
￥62,944 total
includes taxes & fees
May 27 - May 28
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway
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, (8 reviews)
"Welcoming host and cottage as described. Thanks! "
United States
Adam H.
The price is ￥17,478
￥31,083 total
includes taxes & fees
May 25 - May 26
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (11 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 ￥15,918
￥27,538 total
includes taxes & fees
May 25 - May 26
Sassafras Woodland Cabin at Lost Trails
Private kitchen

Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (1 review)
"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 ￥13,992
￥30,808 total
includes taxes & fees
May 25 - May 26
Charming new tiny house-Friendship IN
Exterior detail

Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (26 reviews)
"Everything was great and we were taking care of excellently."
United States
Frank B.
The price is ￥17,490
￥29,336 total
includes taxes & fees
May 25 - May 26
Cedar Rustic 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, (60 reviews)
"Nice friendly town and eating places"
United States
Paul P.
The price is ￥19,875
￥39,313 total
includes taxes & fees
Jun 3 - Jun 4
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
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 ￥42,597
￥94,596 total
includes taxes & fees
Jun 23 - Jun 24
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Exterior

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (33 reviews)
"The place was quiet, well laid out, and exactly as advertised. The snacks and drinks were a nice add-on as well"
United States
Andrew S.
The price is ￥20,034
￥38,581 total
includes taxes & fees
Jun 3 - Jun 4
The Artist’s A-Frame
Exterior detail

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison
9.0 out of 10, Wonderful, (12 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is ￥14,576
￥24,024 total
includes taxes & fees
May 28 - May 29
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
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)
"The area is very quiet with plenty of space to stretch out. Quiet little town with friendly people. "
United States
Karen C.
The price is ￥23,612
￥63,015 total
includes taxes & fees
May 27 - May 28
Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly
Fridge, microwave, oven, stovetop

Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (2 reviews)
"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"
United States
Emily I.
The price is ￥15,900
￥27,507 total
includes taxes & fees
May 28 - May 29
Mulberry Secluded Cabin at Lost Trails
Living area

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

Cozy River View 1BR Near Creation Museum+ Perfect North Slopes
Aurora
The price is ￥20,750
￥36,241 total
includes taxes & fees
May 25 - May 26
Cozy River View 1BR Near Creation Museum+ Perfect North Slopes
Smart TV

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (33 reviews)
"Always a wonderful place to stay!"
United States
Leann L.
The price is ￥17,029
￥33,481 total
includes taxes & fees
May 27 - May 28
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Terrace/patio

"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8

"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
Madison
9.6 out of 10, Exceptional, (12 reviews)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is ￥23,050
￥61,250 total
includes taxes & fees
May 28 - May 29
"Madison Manor I" | Hot Tub, Game Room | 3 BR · 2 Baths · Sleeps 8
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

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

10/10 Excellent
"One night getaway for our anniversary! Check-In process was easy and smooth. Both front desk staff were kind and welcoming.. when they found out it was our anniversary weekend we were surprised with a sweet gift upon returning to our room that evening - we were so surprised and very appreciative of the sweet gesture from the staff! The weather was not ideal for exploring downtown Madison so we decided to hang out at the hotel bar that night - the service, drinks and food were excellent! We had a king room on the top floor and it was very spacious and nice. The only “complaints” I would note would be: the bed was not very soft, shower water did not get very hot, there were some cobwebs in the corners of the bathroom and room, the noise level of others doors shutting in the hallway seemed louder than most places we’ve stayed. However, these things would not deter us from staying here again! Especially a longer stay I would’ve asked about the hot water and a quick dusting of the room. Overall it’s 5 stars and we will return!"
Jessica 1-night trip
Posted 12 hours ago
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

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?

Peaceful getaway centrally located just min. from Madison and Belterra casino.: Visitors like this Bennington vacation home rental. It is located in a rural location and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a hot tub.

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.