Holiday houses in Bennington

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Top-rated holiday rentals in Bennington

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Top Guest favourite
The exterior of a charming single-family home is visible, featuring light blue siding and a front porch with a white railing. Steps lead to the entrance, surrounded by greenery. The neighborhood setting includes nearby houses and clear blue skies.
Home in Sayler Park
4.96 out of 5 average rating, 322 reviews

Nr CVG/Downtown/Perfect North/Creation Museum/OTR

This charming single family home is comfortably furnished and located in the historic village of Sayler Park, just 10 miles from downtown Cincinnati and Over The Rhine and 15 miles from Lawrenceburg, Indiana (Perfect North Slopes, Hollywood Casino, Lawrenceburg Event Center). CVG airport just 6 miles away by Anderson Ferry. The highways and ferry make is easy to get to the Creation Museum and events in Covington and Newport, Kentucky. I would love to host you! Let me know if you have questions.

Top Guest favourite
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, 133 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 favourite
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
4.96 out of 5 average rating, 230 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 favourite
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, 111 reviews

The Dibble Treehouse

Welcome to The Dibble Treehouse! This cozy haven accommodates 4 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 your stay 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 favourite
A charming garden area features a variety of colorful flowers, including vibrant red and bright yellow blooms. The front entrance showcases a distinctive yellow door, flanked by two light blue chairs. A neatly arranged stone border adds structure to the lush greenery surrounding the space.
Guesthouse in Madison
4.93 out of 5 average rating, 109 reviews

The Goataway

Quaint and delightful guesthouse in downtown Madison within walking distance of all the activities and amenities our convivial town has to offer. Perfect for a couple but room for 3 on two large living room sofas. Bessi and Aberforth (aka Abe), the owners goats, live in the backyard seen from the eat-in kitchen. They are super friendly and always up for attention. The space is refreshing, bright and comfortably furnished. You’ll have everything you need for a pleasant stay.

Top Guest favourite
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, 523 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 favourite
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, 178 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 favourite
An indoor pool area is showcased with a bright sky and floor-to-ceiling windows offering scenic views of the surrounding hills. The pool is surrounded by tiled flooring and potted plants, creating a serene setting. Skylights enhance the natural light within the space.
Apartment in Madison
4.99 out of 5 average rating, 166 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.

Guest favourite
A spacious studio is highlighted by exposed brick walls and original wood flooring. A large, white bed features decorative pillows, while a cozy seating area includes a gray sofa. Light enters through large windows, illuminating a small kitchenette and a dedicated work area.
Apartment in Cincinnati
4.95 out of 5 average rating, 405 reviews

Northside Hideaway

The 'Northside Hideaway' is a cozy, quiet studio connected to my newly renovated home nestled in the hills of Mt. Airy Forest in Northside. Just minutes from Clifton, Over The Rhine, and Downtown Cincinnati, It provides the perfect amount of urban serenity. PLEASE NOTE: There is a STRICT TWO GUEST MAXIMUM for all reservations. No exceptions. *Also, there is a 24 HOUR SECURITY camera on the front porch for guests & the space alike.*

Top Guest favourite
Dome in Vevay
4.96 out of 5 average rating, 189 reviews

Hilltop Dome, 42 secluded acres in nature

Our Geodome is tucked away on 42 private acres exclusively for you and your guest Enjoy the stars at night, fire pit, hot tub, high speed internet, washer dryer, and smart TV . The Dome is equipped with a 2 ton mini split that will keep you warm in the winter and cool in the summer We are conveniently located within 15 miles of Madison, IN, Vevay, IN, Clifty Falls, Belterra Casino, also within 62 miles of Cincinnati and Louisville.

Top Guest favourite
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, 187 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 favourite
The cabin features a rustic wooden exterior with a metal roof, surrounded by lush greenery. A wide porch with log railings offers a shaded area, and stairs lead up to the inviting entrance. Multiple seating options can be seen on the porch.
Cabin in Madison
4.99 out of 5 average rating, 217 reviews

Stoney Creek Cabin - Sit back and unwind

Welcome to Stoney Creek Cabin. This charming 2 bedroom cabin is nestled in the hills of Madison, IN. Situated far enough away to offer all the privacy you want, yet only 8 miles from historic downtown, where there are so many gems nearby to explore. Enjoy the HOT TUB, wrap around porch, and patio! There could not be a more relaxing place to unwind.

Popular amenities for Bennington holiday rentals

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