Bennington Vacation Rentals

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Our top choices for Bennington vacation rentals

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 CA $129
CA $244 total
includes taxes & fees
May 9 - May 10
The Blue Door Place

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 CA $137
CA $236 total
includes taxes & fees
May 10 - May 11
Maple Cozy Cabin at Lost Trails

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 CA $241
CA $541 total
includes taxes & fees
May 13 - May 14
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway

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 CA $136
CA $236 total
includes taxes & fees
May 14 - May 15
Walnut Secluded Cabin at Lost Trails

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 CA $194
CA $372 total
includes taxes & fees
May 14 - May 15
Cabin on the Ridge

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 CA $294
CA $722 total
includes taxes & fees
May 9 - May 10
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

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

Cozy River View 1BR Near Creation Museum+ Perfect North Slopes
Aurora
The price is CA $195
CA $330 total
includes taxes & fees
Jun 7 - Jun 8
Cozy River View 1BR Near Creation Museum+ Perfect North Slopes

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 CA $194
CA $352 total
includes taxes & fees
May 21 - May 22
Cabin on the Ridge: The Sequel

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (11 reviews)
"The amenities were in excellent condition and great layout of the property. "
United States
Ed S.
The price is CA $137
CA $236 total
includes taxes & fees
May 26 - May 27
Sassafras Woodland Cabin at Lost Trails

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 CA $150
CA $312 total
includes taxes & fees
May 25 - May 26
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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)
"The host was communicative! The space was clean:) Our pups were cozy! The host sent recommendations as well! Thanks, Laurel! "
United States
Meghan B.
The price is CA $125
CA $239 total
includes taxes & fees
May 19 - May 20
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (31 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 CA $165
CA $332 total
includes taxes & fees
May 19 - May 20
The Artist’s A-Frame

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 CA $182
CA $536 total
includes taxes & fees
May 9 - May 10
Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly

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 CA $120
CA $265 total
includes taxes & fees
May 11 - May 12
Charming new tiny house-Friendship IN

Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (26 reviews)
"The Rustic Cabin was perfect for our quick visit to the Madison area. The place was comfortable and inviting and tucked away ensuring a quiet and relaxing stay."
United States
Rachel L.
The price is CA $150
CA $252 total
includes taxes & fees
May 10 - May 11
Cedar Rustic Cabin at Lost Trails

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 CA $246
CA $394 total
includes taxes & fees
May 9 - May 10
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

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 CA $137
CA $236 total
includes taxes & fees
May 10 - May 11
Mulberry Secluded Cabin at Lost Trails

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, (32 reviews)
"Always a wonderful place to stay!"
United States
Leann L.
The price is CA $146
CA $289 total
includes taxes & fees
May 10 - May 11
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

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 CA $299
CA $695 total
includes taxes & fees
May 9 - May 10
Riverside Storybook Cottage

#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison
10.0 out of 10, Exceptional, (39 reviews)
"Loved this place, very clean and well stocked with the little extras that you always seem to need. "
United States
Matt C.
The price is CA $245
CA $556 total
includes taxes & fees
May 10 - May 11
#207 King Suites, River Views, Deck, Downtown
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

Find out more about Bennington

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Bennington. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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. 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.