Book Holiday Homes in Canaan

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Featured Holiday Homes in Canaan

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
Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River

Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River

Madison
With a stay at this vacation home in Madison, you'll be a 5-minute walk from Thomas Family Winery and 8 minutes by foot from Ohio River.
Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Madison
With a stay at this vacation home in Madison, you'll be within a 5-minute walk of Dr. William Hutching's Office & Hosptal and Historic District.
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
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Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!

Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!

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.
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!
#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park

Madison
The price is AU$854 per night from 1 Jan to 2 Jan
AU$854
includes taxes & fees
1 Jan - 2 Jan 2025
A stay at this vacation home places you in the heart of Madison, steps from Schofield House and Jeremiah Sullivan House.
#209 Kings, River View, Deck, Bicentennial Park
#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown

Madison
The price is AU$854 per night from 1 Jan to 2 Jan
AU$854
includes taxes & fees
1 Jan - 2 Jan 2025
A stay at this vacation home places you in the heart of Madison, steps from Schofield House and Jeremiah Sullivan House.
#207 King Suites, River Views, Deck, Downtown
Beautiful River View spacious 3-bedroom house w/ AC-WiFi- Ark -Creation Museum

Beautiful River View spacious 3-bedroom house w/ AC-WiFi- Ark -Creation Museum

2 out of 5
Aurora
The price is AU$726 per night from 5 Jan to 6 Jan
AU$726
includes taxes & fees
5 Jan - 6 Jan 2025
A stay at this vacation home places you in the heart of Aurora, a 1-minute drive from Ohio River and 10 minutes from Hollywood Casino.
Beautiful River View spacious 3-bedroom house w/ AC-WiFi- Ark -Creation Museum
KY log home close to The Ark Encounter on private 14 acres private seasonal pool

KY log home close to The Ark Encounter on private 14 acres private seasonal pool

Ghent
Located in Ghent, this vacation home is on the waterfront, within a 15-minute drive of Ohio River and Belterra Casino.
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
Secluded Country Home  in Historic Hoosier Hills

Secluded Country Home in Historic Hoosier Hills

Vevay
With a stay at this vacation home in Vevay, you'll be on a lake, and 10.5 mi (17 km) from Ohio River and 14.7 mi (23.7 km) from The Ridge Winery Tasting ...
Secluded Country Home in Historic Hoosier Hills
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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
51 Holiday Homes
Lowest Price
AU$117
Highest Price
AU$854
Popular accommodation
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River, Extremely clean! Beautiful Home 2 Blocks To Main St & 2 Blocks To The Ohio River, Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath, Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!, #209 Kings, River View, Deck, Bicentennial Park, #207 King Suites, River Views, Deck, Downtown, Beautiful River View spacious 3-bedroom house w/ AC-WiFi- Ark -Creation Museum , KY log home close to The Ark Encounter on private 14 acres private seasonal pool, Secluded Country Home in Historic Hoosier Hills

Top trending hotels in Canaan

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel

Madison
The price is AU$345 per night from 20 Jan to 21 Jan
AU$345
includes taxes & fees
20 Jan - 21 Jan 2025
With a stay at this cabin in Canaan, you'll be 10.5 mi (16.9 km) from Ohio River and 16.4 mi (26.3 km) from King's Daughters' Health.
Cabin on the Ridge: The Sequel
Cabin on the Ridge Su

Cabin on the Ridge Su

Madison
With a stay at this cabin in Canaan, you'll be 10.7 mi (17.2 km) from Ohio River and 16.2 mi (26 km) from King's Daughters' Health.
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$246 per night from 24 Dec to 25 Dec
AU$246
includes taxes & fees
24 Dec - 25 Dec
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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Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

2.5 out of 5
525 Dale Drive I 71 Exit 57 Sp, Sparta, KY
Fully refundableReserve now, pay when you stay
The price is AU$117 per night from 25 Dec to 26 Dec
AU$117
includes taxes & fees
25 Dec - 26 Dec
With a stay at Ramada by Wyndham Sparta/At Speedway in Sparta, you'll be 14 mi (22.6 km) from General Butler State Resort Park and 19.1 mi (30.7 km) from Elk ...
Ramada by Wyndham Sparta/At Speedway
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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.