Vacation rentals in Bennington

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Top-rated vacation rentals in Bennington

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Superhost

Apartment in Madison

Stablemaster’s Quarters/ Best downtown location!

The historic building was originally one if the city’s main livery stables circa 1886. It has been used for several businesses in the past but has recently been converted into apartments. New furnishings, bathrooms and kitchen will be appreciated yet the historic charm is blended within. This fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the midwest”. Chicago Tribune says it’s “the best preserved midwest town”.

$150 per night

Superhost

Townhouse in Madison

Cozy downtown home with patio walk to everything.

Your family will be close to everything in downtown Madison when you stay at this conveniently located, updated home built in 1880. First floor open concept floor plan includes living room equipped w/electric fireplace and an eat-in kitchen w/bar stool seating for 4. Upstairs offers two bedrooms and full bath w/shower and old old-fashioned soaker tub. Enjoy nice weather on the fenced back patio. Note: This property contains stairs and is not recommended for guests with mobility issues.

$113 per night

Superhost

Cabin in Madison

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)

$140 per night

Other great vacation rentals in Bennington

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Superhost

Home in Madison

Dog friendly Bungalow one block to Main Street

Cute bungalow has a mixture of old time charm, it was built in 1846! - and new amenities. Easy walk to Main Street, four blocks to the riverfront, short walk to the new Heritage Trial, and short beautiful drive to Clifty Falls. Kitchen is fully equipped including dishwasher, Keurig coffee maker and pods. There is a full size washer and dryer. There is also a little sun porch that is the perfect place to drink your morning coffee. All of our homes are extremely cleaned, wiped down & sanitized

$125 per night

Superhost

Yurt in Madison

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.

$166 per night

Superhost

Loft in Madison

Historic Madison Spa Retreat perfect location

Highlighted on Madison Loft Tours. 1800s historic 3rd story charming Loft offers a spa retreat & private deck. In the midst of Madison’s shopping, dining, festivals & nightlife. Located between Main St and the river. Antique furnishings and beautiful woodwork highlighted. Sip local coffee from our private deck or relax in a jacuzzi tub after touring the sights. Wineries, bars, Mad Paddle Brewery and great restaurants surround us. Hanover College & Clifty Park are minutes away.

$92 per night

Superhost

Guesthouse in Madison

Mulberry Cottage In The Heart Of Downtown Madison

This quaint studio cottage is located in the heart of Madison, Indiana. The entire building was fully renovated in 2020 and offers a modern luxurious stay in our beautiful historic town. This property features off-street parking, fast private WiFi, and complimentary beverages/snacks. Within walking distance of shopping, restaurants, and all downtown events. Few properties come close to the accessibility that this Madison cottage provides. We look forward to hearing from you!

$99 per night

Superhost

Tiny home in Madison

TINY TOO

A Tiny house located in historic Madison, Indiana. Tiny Too is located in the heart of the history of this beautiful river town. Located just steps from the Ohio River, Heritage Trail, quaint shops, local restaurants, wineries and a host of festivals. Step outside the upper and lower decks to river views. Our property is newly remodeled and equipped with all of the amenities of home PLUS outdoor seating (upper/lower decks), gas grill and bicycles. It also offers private, off street parking.

$102 per night

Superhost

Apartment in Madison

River's Edge II-Historic Hunger House-Downstairs

Newly renovated DOWNSTAIRS unit of this historic home in the heart of downtown Madison. Experience the unique blend of historic character and contemporary comfort! Relax on our front porch (complete with swing and river view) after a busy day of touring shops, historic sites, cultural, or music festivals that are the heart of Madison... WELCOME to the River's Edge II! Extended stay (wk-mo) discounts 21%-49% Rent one or both floors (See "River's Edge-UPSTAIRS-listing) SEND INQUIRY FOR PRICING.

$101 per night

Superhost

Cabin in Vevay

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.

$88 per night

Superhost

Cabin in Madison

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.

$119 per night

Superhost

Cabin in Florence

Secluded Cabin on 20 Acres of Classified Forest

Here at Cedar Trails we try our best to provide a great experience for all guests. Very secluded 600sqft cabin but is close to The Ark Encounter, Creation Museum, Belterra and Rising Star Casino. Once you walk inside you'll notice the wood burning stove and the open floor plan. Watch the deer, turkey, fox and rabbits browsing in the field, take a stroll on one of the many trails on the 20-acres or have a bonfire. Please read through rules and look at pictures to make sure it meets your needs.

$98 per night

Superhost

Tiny home in Milton

The Rustic River Retreat.

A perfect getaway in a Brand New home. This Tiny Home was built BIG. It features 1 bedroom with Queen size mattress. The bathroom is equipped with 36” walk in shower, full size toilet, and Washer and Dryer. The Kitchen comes equipped with a cooktop stove, air fryer microwave, Blender, Keurig Coffee maker, large refrigerator, you have access to all basic kitchen needs. Living room couch converts to a full size bed. Easy River Access for kayaking and fishing. Outdoor seating and grill!

$99 per night

Superhost

Home in Madison

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.

$169 per night

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