Bennington Holiday Rentals

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Our top choices for Bennington holiday rentals

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 AU$255
includes taxes & fees
24 Feb - 25 Feb
The Blue Door Place

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (7 reviews)
"Very clean, quiet location. Very relaxing. Host was very helpful. Would definitely stay here again!"
United States
Wendy E.
The price is AU$248
includes taxes & fees
24 Feb - 25 Feb
Sassafras Woodland Cabin at Lost Trails

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (17 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is AU$277
includes taxes & fees
24 Feb - 25 Feb
Cabin on the Ridge: The Sequel

Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
The price is AU$276
includes taxes & fees
24 Feb - 25 Feb
Charming new tiny house-Friendship IN

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
8.8 out of 10, Excellent, (10 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is AU$216
includes taxes & fees
24 Feb - 25 Feb
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (27 reviews)
"This is a fantastic property with attentive hosts! Super easy from start to finish. Clean and homey accommodations. We would definitely choose to stay here again!"
United States
Laura P.
The price is AU$295
includes taxes & fees
24 Feb - 25 Feb
The Artist’s A-Frame

Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (15 reviews)
"Nice cabin"
United States
Nathan M.
The price is AU$303
includes taxes & fees
25 Feb - 26 Feb
Cabin on the Ridge

Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (1 review)
"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 AU$248
includes taxes & fees
24 Feb - 25 Feb
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, (24 reviews)
"Always a wonderful place to stay!"
United States
Leann L.
The price is AU$300
includes taxes & fees
24 Feb - 25 Feb
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

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

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
10.0 out of 10, Exceptional, (2 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 AU$243
includes taxes & fees
25 Feb - 26 Feb
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

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, (55 reviews)
"Nice friendly town and eating places"
United States
Paul P.
The price is AU$315
includes taxes & fees
24 Feb - 25 Feb
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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 AU$529
includes taxes & fees
24 Feb - 25 Feb
Lake House with Private Dock - Ark Encounter & Creation Museum Warsaw Getaway

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, (54 reviews)
"We had a great visit— thank you!!!"
United States
Amy D.
The price is AU$686
includes taxes & fees
24 Feb - 25 Feb
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

Riverside Storybook Cottage

Riverside Storybook Cottage
Aurora
10.0 out of 10, Exceptional, (3 reviews)
"Great time and place!!!"
United States
Brad T.
The price is AU$619
includes taxes & fees
24 Feb - 25 Feb
Riverside Storybook Cottage

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 AU$407
includes taxes & fees
24 Feb - 25 Feb
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

The Madison Inn, Est 1925 Historic suite 107

The Madison Inn, Est 1925 Historic suite 107
Madison
The price is AU$207
includes taxes & fees
8 Mar - 9 Mar
The Madison Inn, Est 1925 Historic suite 107

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

Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly
Warsaw
8.8 out of 10, Excellent, (8 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 AU$525
includes taxes & fees
26 Feb - 27 Feb
Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly

"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)
"We thought the house was great and the location was perfect! We would definitely stay there again. "
United States
Tom or Karen K.
The price is AU$529
includes taxes & fees
1 Mar - 2 Mar
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison
10.0 out of 10, Exceptional, (37 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 AU$580
includes taxes & fees
24 Feb - 25 Feb
#207 King Suites, River Views, Deck, Downtown

East Main Lofts - Coastal 201

East Main Lofts - Coastal 201
Madison
9.8 out of 10, Exceptional, (9 reviews)
"This was a perfect spot for us for a long weekend stay. The place was very clean and the host had great instructions/recommendations etc. "
United States
Missy R.
The price is AU$578
includes taxes & fees
24 Feb - 25 Feb
East Main Lofts - Coastal 201
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

Everything you need to know about Bennington holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Bennington holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Bennington holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Bennington. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Bennington holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Bennington holiday rentals we have selected for you start as low as AU$243 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best Bennington holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Bennington rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Bennington holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Bennington. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Bennington?

Yes, there are holiday rentals close to the most popular sights in Bennington, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Bennington has to offer?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: This holiday home rental outside of Bennington 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 wider area.

What’s a holiday rental in Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bennington. Holiday rentals offer extras such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.