Skip to content

Vacation rentals in Bennington

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Bennington

Guests agree: these stays are highly rated for location, cleanliness, and more.

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!
$105 per night
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
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)
$153 per night

Other great vacation rentals in Bennington

Private room in Bennington
Peaceful Country Experience
$90 per night
Home in Madison
Main Street Retreat
$109 per night
Private room in Dillsboro
C-Adorable single room in Dillsboro, IN
$60 per night
Rental unit in Madison
Stablemaster’s Quarters/ Best downtown location!
$158 per night
Home in Madison
The Artist’s A-Frame
$120 per night
Cottage in Madison
Cozy Farmhouse Retreat in Historic District
$99 per night
Home in Madison
The Tucker, by Golden Retreats
$120 per night
Home in Madison
Little Pink House north
$126 per night
Guesthouse in Madison
Mulberry Cottage In The Heart Of Downtown Madison
$103 per night
Home in Vevay
Secluded Country Home in Historic Hoosier Hills
$180 per night
Rental unit in Madison
The Treehouse
$164 per night
Rental unit in Aurora
Studio Apartment w/ Beautiful View!
$80 per night

Other types of stays on Airbnb

  1. Airbnb
  2. United States
  3. Indiana
  4. Switzerland County
  5. Bennington