Vacation rentals in Bennington

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Bennington

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

An exterior view of the reconstructed stone schoolhouse is shown, featuring a peaked roof and a large entry door. Two potted plants flank the entrance. A leafy tree provides shade on a grassy area, with open fields visible in the background under a clear blue sky.

Home in Versailles

4.96 out of 5 average rating, 135 reviews

School Days

Sharpen your pencils and reminisce about your childhood school days in this beautifully reconstructed schoolhouse. Built in 1879, this gorgeous property is situated just minutes from local coffee shops, locally owned restaurants, antique shops and the second largest State Park in Indiana. Be entertained with live music, museums, and other attractions by visiting three conveniently located cities. Come enjoy the modern amenities as well as the historical features this schoolhouse has to offer.

Guest favorite

A spacious bedroom features a comfortable bed with white linens, complemented by a tufted bench at the foot. Exposed brick walls contrast with sleek modern appliances in the kitchen area, while warm wood flooring and soft lighting create a cozy ambiance.

Apartment in Aurora

4.85 out of 5 average rating, 114 reviews

Studio Apartment w/ Beautiful View!

Come and stay a while in this charming and unique studio apartment. Located in the heart of historical Aurora, IN, you can walk to all the shops, parks and restaurants! Step out onto your private patio and enjoy your view of the Ohio River! It’s the perfect romantic getaway. We are also pet friendly so if you want to bring your furry friends we are happy to host them as well, just be aware that there is a $100 fee that covers our additional cost. Just add them with your guests at checkout.

Top guest favorite

The cabin features a rustic exterior with wooden siding and a blue metal roof. A stone chimney is visible on one side. The surrounding area displays fallen leaves and bare trees, indicating a tranquil natural setting.

Cabin in Vevay

4.98 out of 5 average rating, 118 reviews

The Cabin

As you walk in, The Cabin wraps it's arms around you and says " Welcome home." You can feel the stress leave you as you settle in for your stay at this scenic cabin on 9.8 wooded acres. Fully furnished, spacious 1 room cabin with stone wood burning fireplace, equipped kitchen, bath with shower and twin over queen bunk bed. Refresh your mind & soul on the covered back porch overlooking the mature woods. Enjoy watching the abundant wildlife, including turkeys, deer, chipmunks and squirrels.

Guest favorite

A yurt is shown surrounded by expansive green grass under a clear blue sky. Contrails from passing aircraft create intersecting lines overhead, while sunlight shines brightly behind the structure, enhancing the tranquil outdoor setting.

Yurt in Madison

4.95 out of 5 average rating, 216 reviews

Madison's only Yurt experience!!!

You'll love this unique and romantic escape in the hills of southern Indiana! Located just 20 minutes from beautiful downtown Madison and Vevay. Enjoy the countryside in your very own yurt. Come relax after a hard day of shopping in downtown Madison or after a late night at Belterra casino. You will love the warm inviting boho style of decor while enjoy the beautiful sunsets from the deck. The stars look so close you could touch them from the grassy hillsides of this enchanting property.

Guest favorite

The exterior of the container cabin features a wooden pergola, providing shade over a cozy seating area. Barrels and stones are positioned along the pathway, leading to large glass doors that open to the living space, surrounded by greenery and open fields.

Cabin in Owenton

4.85 out of 5 average rating, 450 reviews

Vintage Container Cabin on Beautiful Farm Near Ark

Discover the festive charm of our fully renovated container cabin, nestled along the wooded ridge of our farm. Enjoy the crisp winter air as you explore 200 acres of beauty, or relax by the fire with a glass of local Kentucky bourbon. The cabin features a custom-built design with treasures from around the farm, blending vintage charm of Kentucky's past. Grill up a holiday feast, cozy up on the memory foam mattress, and soak in the beauty of winter from the comfort of your own cozy cabin.

Top guest favorite

The exterior of a house is shown at sunset, featuring a welcoming porch adorned with lights. A clear pathway leads to the front door, flanked by trees. Soft glow from the house highlights the inviting atmosphere, and a decorated wreath is visible on the door.

Home in Florence

4.96 out of 5 average rating, 134 reviews

The Little Farm House

Relax with the whole family at this peaceful place to stay. King size bed in master bedroom and garden tub in master bath. There is also a full bathroom just as you enter the the back door. There are no bathrooms upstairs however, there are two bedrooms and each bedroom has a queen size bed and two twins beds built in the wall. Beautiful scenery no matter what side of the house your on. Relax on the wrap around porch and enjoy the unforgettable sunsets and different types of wildlife.

Top guest favorite

The floating home is illuminated warmly, showcasing large windows that reveal the interior. A wooden dock lines the side of the houseboat, with a railing providing safety. The setting includes lush greenery in the background, enhancing the peaceful atmosphere.

Houseboat in Florence

4.91 out of 5 average rating, 184 reviews

Peaceful Houseboat off the Ohio River

This floating home is located in a beautiful setting in a cove off the Ohio River. Drive to nearby towns and visit antique shops and restaurants in Vevay and Madison, Indiana. Clifty Falls is a great place to hike. Beltera Casino Resort is down the street and the marina is also close to Rising Sun, Hollywood Casino, and Sunset Grill on the water in Warsaw, Kentucky. Conveniently located close to The Neeley Family Distillery. Some have visited the Ark while staying here also.

Guest favorite

The cabin exterior is softly illuminated by string lights, creating a warm ambiance. Wood siding complements the design, while tall windows enhance the visual appeal. A small patio area with chairs invites relaxation in the tranquil wooded setting.

Cabin in Madison

4.98 out of 5 average rating, 487 reviews

Cabin on the Ridge: The Sequel

Welcome to the area's first new construction short term rental tailored for you, the guest. This contemporary cabin is nestled in the woods right in the heart of Amish country. This is the perfect destination for those who want to getaway yet enjoy the unique beauty of Historic Downtown Madison (25 minutes) recognized as "The prettiest small town in the Midwest" or chase waterfalls at Clifty Falls State Park (25 minutes). •Fast wifi •Roku TV •Keurig (K-Cups Available)

Top guest favorite

The exterior of the property showcases a welcoming entrance surrounded by lush greenery and vibrant flowering shrubs. A wooden deck is visible in front, complemented by neat landscaping and a well-maintained lawn, providing a serene and inviting atmosphere.

Home in Vevay

4.96 out of 5 average rating, 174 reviews

Secluded Country Home in Historic Hoosier Hills

You’ll love the property because of the private secluded location and the views. The property is good for couples, solo families (with kids), all girls/boys gatherings and big groups. The house has over 1900 square feet of living space plus a sunroom looking over the pond and woods. There are two TVs with cable connection and one tv with an antenna. One TV is in the common living area and the other tv's are in two bedrooms, Catch and release fishing is permitted.

Top guest favorite

An inviting living area features a plush gray sofa adorned with decorative pillows. A wooden coffee table occupies the center, and a contemporary lamp stands beside a cozy chair. Light filters through the sliding glass doors, reflecting off the warm wooden floors.

Cabin in Versailles

4.98 out of 5 average rating, 143 reviews

Mamaws Cabin Hot tub, Creation Museum/ARK, Hiking

Spacious cabin (1100 sq feet) was once Mamaw's home. Sleeps 2 private and 4 more semi-private, 6 people total. Built in a primitive country style, it features a Loft bedroom that sleeps 3, an additional small bedroom that sleeps 1 and a Master Bedroom with Queen- size Sleep Number Bed. Fully functional kitchen and bath including washer/dryer. Outdoor fire-pit and hot tub. ROKU TV/ DVDs, No cable. Wii gaming system. WiFi available.

Top guest favorite

The exterior of a two-story brick Victorian house showcases a welcoming entrance with steps leading to a covered porch. Large windows allow ample natural light, and a well-maintained front yard complements the classic architectural features.

Home in Dillsboro

4.97 out of 5 average rating, 178 reviews

Spacious home in a quaint small town setting

This is a 1888 Victorian style two story brick house set in a neighborhood of older homes. Newly renovated with a fully equipped kitchen, laundry facility, dining room, living room, bedroom and 1 1/2 bathrooms on first floor. The second floor has three bedrooms and 2 full bathrooms. Each upstairs bedroom has a Smart TV and the living room has a Smart TV. It has a pleasant back yard with outdoor sitting and onsite parking.

Top guest favorite

A spacious two-story home with a distinctive red metal roof sits on a well-maintained grassy area. Surrounding trees and shrubs complement the landscape, while a gravel driveway leads to a nearby garage. A peaceful setting is showcased, with open fields visible in the background.

Home in Madison

5 out of 5 average rating, 112 reviews

Vineyard Château - peaceful country setting!

Forget your worries in this spacious and serene space. A beautiful three bedroom home, located between two historic towns of Vevay and Madison, Indiana. Perfect location for some rest & relaxation. Private country setting, just a short drive away from antiques, restaurants, state parks, and Splinter Ridge Hunting Reserve. Please note: The home is located 13 miles east of downtown Madison, approximately a 20 minute drive.