Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Top guest favorite

The exterior view showcases a charming entry with a covered porch and a well-maintained lawn. A seated area with chairs is present, complemented by vibrant flower pots. The siding features a neutral color, and large windows provide an inviting appearance.

Guest suite in Batesville

4.98 out of 5 average rating, 188 reviews

Modern Private Entrance Studio Apt extended/nitely

New fully furnished 2-nd floor studio apartment in quiet up-scale neighborhood. Keyed private entry to indoor stairwell. Approx 800 sq-ft. Hardwood floors, great room, very large windows, lots of light. Floor plan with full kitchen & seating area, living area w/ sofa, chairs, ottomans. Sleeping section includes queen bed adjacent to 3/4 bath. Wi-Fi, USB charg-ports at bedside and desk lamp. Wall mounted 164 channel fiber-optic 32-inch HD flat screen TV with HBO, Starz, Sports, premium channels.

Top guest favorite

A historic cabin is nestled among lush greenery, showcasing a log design. A covered front porch extends from the cabin, providing a shaded area. Steps lead from the garden filled with ferns and flowers down to the riverside, where tranquility can be enjoyed.

Cabin in Union

4.87 out of 5 average rating, 107 reviews

Rustic Cabin on the Ohio River.

If you're looking for marble countertops, this may not be your place. But if you’re seeking quiet, character, and a taste of how things used to be, with a modern twist, welcome to our 1800s-era cabin. Renovated in 2022, the cabin is comfy but you can expect creaky floors, original woodwork, and a few quirks that come with age. The cabin is authentic, and thoughtfully kept. You will have TV, wifi, central heat, air conditioning but expect to hear the water pump run and there is no dishwasher.

Guest favorite

Cabin in Owenton

4.85 out of 5 average rating, 452 reviews

Rustic Container Cabin • Farm Stay • Near Ark

Discover the charm of our rustic container cabin on a wooded ridge of our family farm. Freshly painted exterior—same comfy interior. 30 min to Ark Encounter. Unwind on the sunset porch under string lights, enjoy the fire pit & grill, and breathe crisp Kentucky air as you explore 200 acres of hills and trails. Inside: vintage farm touches, comfy memory-foam bed(s), efficient kitchenette, heat/AC, and a one-of-a-kind bath. A peaceful base for the Ark and Boutbon Trail. A true Kentucky farm stay.

Top guest favorite

The exterior of a historic two-story building is presented, featuring a white facade with distinctive architectural details. Warm lighting illuminates the entrance and surrounding area, while a tree with sparse branches is visible in the foreground. The setting reflects a calm evening atmosphere.

Apartment in Lawrenceburg

4.96 out of 5 average rating, 124 reviews

The Dunn Houses on Elm Row

Welcome to the Dunn Houses on Elm Row, we are 15 mins, from CVG Airport and the Cincinnati/N.Kentucky area. We have the quaintness of a small town, but the ability to keep you busy. You can try your hand at slots, enjoy a concert, dine at one of many restaurants/bar, or enjoy nature with the bike/walking trail or the many parks locally. At the Dunn Houses, we will go out of our way to make your stay memorable. We hope when you stay with us, you experience what makes Lawrenceburg so special.

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, 138 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.

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, 121 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, 219 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

A gravel pathway meanders through trees displaying hints of autumn color, leading toward an open grassy area. The clear blue sky complements the natural surroundings, while power lines are subtly visible in the distance.

Farm stay in Glencoe

4.97 out of 5 average rating, 150 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)

Top guest favorite

A serene view of Bullock Pen Lake is captured, showcasing calm waters reflecting the fluffy clouds above. The lush greenery lines the shore, creating a peaceful atmosphere ideal for relaxation. Bright blue skies dominate the scene, enhancing the natural beauty of the landscape.

Cottage in Crittenden

5 out of 5 average rating, 121 reviews

Lake Front w/ POOl! Between Ark & Creation Museum.

If you are looking to experience lake life, look no further! Our Guest House sits on the beautiful 140 acre Bullock Pen Lake. It's a great place to relax, or enjoy kayaking, paddle boating, paddle boarding and fishing. We have one of the best views of the lake. The Guest House is fully renovated and decorated with relaxation in mind. It has everything you would need for your stay. After all, the lake is where your worries fade and memories are made! (The pool is now OPEN! 5/9/25)

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, 185 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

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, 490 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)

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.