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Bennington Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Bennington vacation rentals

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.
$228 nightly
The price is $262
Jul 28 - Jul 29
Total with taxes and fees
Cabin on the Ridge
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.
$215 nightly
The price is $247
Jul 29 - Jul 30
Total with taxes and fees
Cabin on the Ridge: The Sequel
Private kitchen

Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (3 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.
$173 nightly
The price is $194
Jul 27 - Jul 28
Total with taxes and fees
Charming new tiny house-Friendship IN
Interior

King Bed|Non-Smoking

King Bed|Non-Smoking
Aurora, IN
10.0 out of 10, Exceptional, (74 reviews)
"Four nights of peace in Aurora! Quiet location close to local attractions like the Creation Museum was really handy for us."
United States
Anonymous traveler
$74 nightly
The price is $82
Aug 9 - Aug 10
Total with taxes and fees
King Bed|Non-Smoking
Exterior

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
$155 nightly
The price is $173
Jul 26 - Jul 27
Total with taxes and fees
Sassafras Woodland 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, (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.
$155 nightly
The price is $173
Jul 26 - Jul 27
Total with taxes and fees
Maple Cozy 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, (8 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
$155 nightly
The price is $173
Jul 27 - Jul 28
Total with taxes and fees
Walnut Secluded Cabin at Lost Trails
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
10.0 out of 10, Exceptional, (1 review)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
$147 nightly
The price is $169
Aug 10 - Aug 11
Total with taxes and fees
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
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.
$165 nightly
The price is $185
Jul 27 - Jul 28
Total with taxes and fees
Cedar Rustic Cabin at Lost Trails
Interior

King Bed|Smoking|Aurora

King Bed|Smoking|Aurora
Aurora, IN
10.0 out of 10, Exceptional, (70 reviews)
"Room offered great privacy which is important when traveling with family, would definitely come back next time we're in town!"
United States
Anonymous traveler
$74 nightly
The price is $82
Aug 9 - Aug 10
Total with taxes and fees
King Bed|Smoking|Aurora
Exterior detail

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison
9.6 out of 10, Exceptional, (19 reviews)
"Conveniently located close to downtown area. Room was comfortable and clean."
United States
Darin
$148 nightly
The price is $158
Aug 23 - Aug 24
Total with taxes and fees
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Interior

2 Queen Beds|Non Smoking

2 Queen Beds|Non Smoking
Aurora, IN
10.0 out of 10, Exceptional, (76 reviews)
"Daily housekeeping ensured everything stayed neat, making our visit enjoyable."
United States
Anonymous traveler
$81 nightly
The price is $91
Aug 9 - Aug 10
Total with taxes and fees
2 Queen Beds|Non Smoking
Property grounds

2 Queen Bed Smoking | Hillcrest

2 Queen Bed Smoking | Hillcrest
Aurora, IN
10.0 out of 10, Exceptional, (72 reviews)
"Great spot near local attractions. Clean rooms and easy parking."
United States
Anonymous traveler
$81 nightly
The price is $91
Aug 9 - Aug 10
Total with taxes and fees
2 Queen Bed Smoking | Hillcrest
Coffee/tea maker, fridge, microwave, oven

Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.6 out of 10, Exceptional, (4 reviews)
"This is a total hidden gem! The cabin seemed brand new and was outfitted with everything you might need. We spent our 25th wedding anniversary weekend here and loved every second! Would highly recommend!"
United States
Jodi E.
$155 nightly
The price is $173
Jul 26 - Jul 27
Total with taxes and fees
Mulberry Secluded Cabin at Lost Trails
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, (14 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.
$173 nightly
The price is $198
Aug 10 - Aug 11
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior

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

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison
$202 nightly
The price is $232
Jul 26 - Jul 27
Total with taxes and fees
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
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.
Waterfront Cabin | Near ARK | Large Family Retreat
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, (69 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.
$216 nightly
The price is $248
Jul 26 - Jul 27
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Pool

#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison
10.0 out of 10, Exceptional, (71 reviews)
"Couldnt recommend more! Great place and hosts!"
United States
Zach D.
$343 nightly
The price is $404
Jul 26 - Jul 27
Total with taxes and fees
#209 Kings, River View, Deck, Bicentennial Park
Exterior

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (37 reviews)
"Everything was absolutely wonderful "
United States
Michael (alex) W.
$206 nightly
The price is $237
Jul 29 - Jul 30
Total with taxes and fees
The Artist’s A-Frame
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

Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

10/10 Excellent
"They still got a Gideon's Bible in the room, keep it up! 👍 Room was clean. Great for the affordable price +"
Simon 3-night trip
Posted 3 hours ago
Ramada by Wyndham Sparta/At Speedway

Find out more about Bennington

Everything you need to know about Bennington vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Bennington vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Bennington vacation 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 low season months. For more hustle and bustle, you may prefer to visit Bennington in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $169 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Bennington rentals

At Expedia, we put the best Bennington vacation 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 vacation.

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 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.