Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Top guest favorite

An aerial view captures a rustic farm landscape with rolling green hills and patches of trees. The layout includes several structures, including a barn, a main house, and a camper cabin, surrounded by open fields and winding paths. The natural beauty of the property is highlighted by its expansive rural setting.

Farm stay in Owenton

4.94 out of 5 average rating, 127 reviews

Vintage Camper Cabin on Beautiful Farm Near Ark

Feel refreshed when you stay in this rustic gem. This listing features a newly converted pop up camper cabin. Truly a one of a kind. Everything has been updated with all the modern amenities while still providing that rustic appeal you've been looking to experience. You'll find yourself nestled next to the woods on the ridge of our beautiful family farm. Enjoy over 200 acres by hiking our hills, pond fishing, swimming the creek, grilling some steaks all while sipping on some fine Bourbon.

Guest favorite

Home in Versailles

4.95 out of 5 average rating, 116 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.

Superhost

The kitchen features an arched brick wall with modern cabinetry and stainless steel appliances. Wood countertops complement the rich hardwood flooring. A polished chandelier hangs above, providing a blend of contemporary and historic elements in the space.

Apartment in Aurora

4.84 out of 5 average rating, 106 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

Two wooden rocking chairs are positioned on a wooden deck, facing a large window that overlooks a natural setting filled with autumn foliage. A grill is seen nearby, and fallen leaves cover the ground, adding to the tranquil outdoor environment.

Cabin in Vevay

4.98 out of 5 average rating, 108 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 collection of freshly gathered eggs is resting in a soft green fabric. The eggs display a range of colors including shades of brown, white, and pale blue, resting comfortably together in a natural setting.

Yurt in Madison

4.96 out of 5 average rating, 207 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.

Top guest favorite

The great room features vaulted wooden ceilings and a mix of natural light from large windows. A comfortable seating area includes a taupe sectional sofa facing an electric fireplace, with a dining space and kitchen visible in the background. Warm wood tones create a welcoming environment.

Cabin in Madison

4.98 out of 5 average rating, 719 reviews

Cabin on the Ridge

Welcome to Cabin on the Ridge, your tranquil retreat nestled in the scenic hills of Madison, Indiana. Just 25 minutes from downtown Madison, our cabin offers a perfect blend of rustic charm and modern comfort. Madison, awarded the “Best Small Town in the Midwest” by USA Today and the Great American Main Street Award, is a must-visit. Enjoy the historic architecture, boutique shops, and delightful eats, or explore Clifty Falls State Park. •Fast wifi •Roku TV/Streaming services •Keurig

Top guest favorite

A carton containing ten eggs is displayed. Each egg varies in tone, ranging from light beige to brown. The carton is made of recycled material and includes nutritional information printed on the top.

Farm stay in Glencoe

4.96 out of 5 average rating, 124 reviews

Carriage House w King bed, Lux bath, amazing views

Take in the views at this unique and tranquil getaway. This home is part of our beautiful 50-acre working farm where you can regularly see wildlife and heritage breed farm animals. And although it sits nestled on the back ridge, it is also just a short drive to many of Kentucky and Cincinnati's amazing sites. Our farm values caring for earths resources, so we have intentionally created this space with solar power, and toxic free cleaning products. (note: 2nd bed is a deluxe airmatress)

Guest favorite

Houseboat in Florence

4.91 out of 5 average rating, 176 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.

Top guest favorite

Home in Vevay

4.96 out of 5 average rating, 169 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

Two young goats interact in a rustic setting. One goat has a light brown coat with white markings, while the other is black with white. Both wear bright green harnesses, and a hand reaches out to them in a gesture of feeding or petting.

Bungalow in Dry Ridge

4.98 out of 5 average rating, 707 reviews

The Cute Little House Near The Ark Encounter

The "Little House" is a cute 1 bedroom house located on our farm in a beautiful country setting with 6 acres of outdoor space for relaxing. It is separate from our home and is all yours. It is conveniently located only 8 miles from the Ark Encounter and you only need to make one turn to get there. We have chickens, ducks, turkeys, a horse, and 11 goats. We also have a 1/2 mile nature trail to explore with a scavenger hunt, and a campfire spot with free firewood.

Top guest favorite

A serene view of lush green trees stretches out, showcasing the natural landscape and rolling hills. The image captures the vibrant foliage under a partially cloudy sky, creating a peaceful atmosphere within the secluded setting.

Apartment in Madison

4.98 out of 5 average rating, 118 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Top guest favorite

The exterior of a spacious home is framed by a well-kept lawn and vibrant shrubs. A red metal roof contrasts with the light-colored siding. Two asymmetrical dormer windows enhance the facade, while a gravel driveway leads toward the entrance adorned with decorative elements.

Home in Madison

5 out of 5 average rating, 109 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.