Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Guest favorite
Cabin in Owenton
4.86 out of 5 average rating, 468 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 modern treehouse is showcased with a yellow deck extending from the entrance, situated on a gravel driveway. Large windows invite natural light, while the surrounding trees add to the natural setting. The structure appears elevated, resting on concrete stilts.
Treehouse in Rising Sun
4.98 out of 5 average rating, 102 reviews

The Dibble Treehouse

Welcome to The Dibble Treehouse! This cozy haven accommodates 4-6 guests and boasts all the amenities for an unforgettable stay. Relax in the hot tub or sauna, gently swing in the suspended bed or hanging chairs, and savor meals at the outdoor picnic table. The full kitchen is equipped for culinary adventures and the wrap around porch offers stunning views. Enjoy evenings by the fire pit or take in your favorite shows on the smart TV. Book this stay to fully recharge and reconnect with nature!

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, 141 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.

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
4.95 out of 5 average rating, 145 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 cozy sleeping area features light wood paneling and a spacious bed adorned with blue and floral bedding. A striking black and white artwork hangs on the wall, complemented by a vintage-inspired hanging light fixture. Natural light enters through the window, enhancing the serene environment.
Tiny home in Florence
4.85 out of 5 average rating, 116 reviews

New Tiny House, Ohio River view, running water,

This small, 1 room, new tiny house called “The Lite House” is decorated shabby chic and located in a beautiful wooded setting facing a cove at a marina with views of the water on the Ohio River. Catch beautiful sunrises here. There are shared places on the property guests can use while staying, a covered shelter with grills, supplies, tables, chairs, fire pit, side walks. You will use the restrooms in the shelter, just 5 steps away from your door. Umbrella provided in tiny house. See photos.

Superhost
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
4.84 out of 5 average rating, 124 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, 126 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.

Top 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, 222 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 cabin showcases a rustic exterior made of natural wood, featuring a welcoming front porch with wooden railings. Surrounding foliage displays autumn colors, enhancing the serene setting. A driveway leads to a garage door, while steps ascend to the main entry of the cabin.
Cabin in Madison
4.98 out of 5 average rating, 745 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

Guest favorite
A single-story house displays a welcoming exterior with beige siding and red shutters. A manicured lawn is complemented by colorful flowers and shrubs in front. A solid pathway leads to the entrance, with a mailbox positioned at the edge of the property.
Home in Osgood
4.93 out of 5 average rating, 120 reviews

Wilmer Crash Pad: Simple home, includes breakfast

It's a simple 2 bed, 1 bath house that is perfect for short or long stays, depending on your needs. It is on a quiet, dead-end street with a relaxing vibe. The home is well-equipped with *everything* you would need for daily life. Family friendly with toys, games, etc. Blow-up mattress and futon for extra sleepers. Keyless entry. Two car detached garage. Perfect for work trips or area visits. One hour from Cincy, 75 minutes to Indy, 90 minutes to Louisville, 20 minutes to Batesville.

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, 129 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 closed!)

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, 176 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.

Popular amenities for Bennington vacation rentals

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