Book Holiday Homes in Canaan

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Featured Holiday Homes in Canaan

Peaceful getaway  centrally located just min. from Madison and Belterra casino.

Peaceful getaway centrally located just min. from Madison and Belterra casino.

Vevay
Located in Vevay, this vacation home is in a rural location, within a 15-minute drive of Switzerland County Public Library and Hoosier Theater.
Peaceful getaway centrally located just min. from Madison and Belterra casino.
The Wadsworth in National Historic District of Madison, Indiana.

The Wadsworth in National Historic District of Madison, Indiana.

Madison
A stay at this vacation home places you in the heart of Madison, within a 15-minute walk of Thomas Family Winery and Ohio River.
The Wadsworth in National Historic District of Madison, Indiana.
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

Madison
With a stay at this vacation home in Madison, you'll be within a 10-minute walk of Dr. William Hutching's Office & Hosptal and Historic District.
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
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Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Madison
The price is AU$359 per night from 1 Apr to 2 Apr
AU$359
includes taxes & fees
1 Apr - 2 Apr
With a stay at this vacation home in Madison, you'll be a 5-minute walk from Ohio River and within a 5-minute drive of Thomas Family Winery.
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

Madison
A stay at this vacation home places you in the heart of Madison, steps from Ohio River and 3 minutes by foot from Thomas Family Winery.
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly

Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly

Warsaw
Located in Warsaw, this vacation home is a 4-minute drive from Smugglers Cove and 8 minutes from Markland Dam Park.
Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly
Never Too Far
 Spacious house on dead end road with great outdoor space!

Never Too Far Spacious house on dead end road with great outdoor space!

Aurora
The price is AU$493 per night from 13 Apr to 14 Apr
AU$493
includes taxes & fees
13 Apr - 14 Apr
With a stay at this vacation home in Aurora, you'll be within a 10-minute drive of Ohio River and Hillforest.
Never Too Far Spacious house on dead end road with great outdoor space!
Red comfy cottage

Red comfy cottage

Madison
Located in Madison, this vacation home is a 3-minute drive from Clifty Falls State Park and 5 minutes from Lanier Mansion.
Red comfy cottage
Madison's Only YURT Experience

Madison's Only YURT Experience

Madison
With a stay at this vacation home in Madison, you'll be 7.4 mi (12 km) from Ohio River and 8.7 mi (13.9 km) from Switzerland County Public Library.
Madison's Only YURT Experience
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Canaan Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Canaan vacation homes are the perfect way for you to wing it.

Holiday houses in Canaan let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Canaan in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Canaan adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Canaan with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Canaan vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Canaan Holiday Homes essential information

Accommodation
57 Holiday Homes
Lowest Price
AU$163
Highest Price
AU$493
Popular accommodation
Peaceful getaway centrally located just min. from Madison and Belterra casino., The Wadsworth in National Historic District of Madison, Indiana. , Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River, Glenda’s Overlook..everything you need to make visiting Madison a great getaway!, Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St, Waterfront Cabin w/ A View! Large Family Retreat + Pet-Friendly, Never Too Far Spacious house on dead end road with great outdoor space! , Red comfy cottage , Madison's Only YURT Experience

Top trending hotels in Canaan

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel

Madison
The price is AU$373 per night from 14 Apr to 15 Apr
AU$373
includes taxes & fees
14 Apr - 15 Apr
With a stay at this cabin in Canaan, you'll be 10.5 mi (16.9 km) from Ohio River and 13.5 mi (21.7 km) from Switzerland County Public Library.
Cabin on the Ridge: The Sequel
Cabin on the Ridge Su

Cabin on the Ridge Su

Madison
The price is AU$402 per night from 14 Apr to 15 Apr
AU$402
includes taxes & fees
14 Apr - 15 Apr
With a stay at this cabin in Canaan, you'll be 10.7 mi (17.2 km) from Ohio River and 13.7 mi (22 km) from Switzerland County Public Library.
Cabin on the Ridge Su
Belterra Casino Resort

Belterra Casino Resort

3.5 out of 5
777 Belterra Drive, Florence, IN
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 6 Apr to 7 Apr
AU$276
includes taxes & fees
6 Apr - 7 Apr
With a stay at Belterra Casino Resort in Florence, you'll be on the waterfront, just a 5-minute walk from Belterra Casino and 9 minutes by foot from Ohio ...
Belterra Casino Resort
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Hillside Inn

Hillside Inn

2.5 out of 5
831 E Main St, Madison, IN
Fully refundable
The price is AU$163 per night from 2 Apr to 3 Apr
AU$163
includes taxes & fees
2 Apr - 3 Apr
With a stay at Hillside Inn in Madison, you'll be within a 15-minute walk of Thomas Family Winery and Ohio River.
Hillside Inn
Don't see what you're looking for?
See all available properties in Canaan
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.