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Vacation rentals in Canaan

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Top-rated vacation rentals in Canaan

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

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”.
$149 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.
$104 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)
$138 per night

Other great vacation rentals in Canaan

Superhost
Home in Madison
Dog friendly Bungalow one block to Main Street
$125 per night
Superhost
Guesthouse in Madison
Mulberry Cottage In The Heart Of Downtown Madison
$99 per night
Superhost
Apartment in Madison
Dragonfly Suite
$90 per night
Superhost
Loft in Madison
Historic Madison Spa Retreat perfect location
$87 per night
Superhost
Tiny home in Madison
TINY TOO
$102 per night
Superhost
Apartment in Madison
River's Edge II-Historic Hunger House-Downstairs
$101 per night
Superhost
Home in Madison
Carole's Cottage
$75 per night
Superhost
Cabin in Madison
Stoney Creek Cabin - Sit back and unwind
$119 per night
Superhost
Tiny home in Milton
The Rustic River Retreat.
$99 per night
Superhost
Apartment in Madison
The Treehouse - Hot Tub - Indoor Pool Get Away!
$183 per night
Superhost
Home in Madison
The Ogden, by Golden Retreats
$125 per night
Superhost
Home in Madison
Charming shotgun in the heart of downtown Madison
$100 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Indiana
  4. Jefferson County
  5. Canaan