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Canaan Holiday Rentals

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Canaan holiday rentals

TV, fireplace

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is HK$1,113
HK$2,019 total
includes taxes & fees
2 Aug - 3 Aug
Cabin on the Ridge: The Sequel
TV, fireplace, DVD player

Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is HK$1,113
HK$2,091 total
includes taxes & fees
2 Aug - 3 Aug
Cabin on the Ridge
Interior

604 GQ on Mulberry: 2 King Luxury Suites, Patio

604 GQ on Mulberry: 2 King Luxury Suites, Patio
Madison
604 GQ on Mulberry: 2 King Luxury Suites, Patio
Property grounds

Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (4 reviews)
"A lovely accommodation! The cabin was spotless, well kept and comfortable, and the property was private and quiet. Great hosts that were very responsive and quick to help with anything. Would absolutely recommend!"
United States
Shirley Z.
The price is HK$847
HK$1,212 total
includes taxes & fees
14 Jul - 15 Jul
Briar Ridge Cabin in Osgood IN
Interior

King Bed|Non-Smoking

King Bed|Non-Smoking
Aurora, IN
10.0 out of 10, Exceptional, (74 reviews)
"Spacious common areas by the outdoor fireplace were nice for mingling with neighbors."
United States
Anonymous traveller
The price is HK$577
HK$646 total
includes taxes & fees
22 Jul - 23 Jul
King Bed|Non-Smoking
Private kitchen

Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (2 reviews)
"This tiny home was exactly what we had expected. Very clean, nice and welcoming. The owners were great and communication was excellent. We will be sure to see if it is Ava when we come to visit family again. "
United States
Randall B.
The price is HK$690
HK$1,519 total
includes taxes & fees
20 Jul - 21 Jul
Charming new tiny house-Friendship IN
Terrace/patio

Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (6 reviews)
The price is HK$784
HK$1,356 total
includes taxes & fees
19 Jul - 20 Jul
Walnut Secluded Cabin at Lost Trails
Outdoor dining

Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
10.0 out of 10, Exceptional, (17 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
The price is HK$470
HK$1,528 total
includes taxes & fees
13 Jul - 14 Jul
Modern cabin very close to scenic riverfront walks
Property grounds

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.6 out of 10, Exceptional, (12 reviews)
"Host was very accommodating and this place was perfect for a place to stay while visiting friends. Everything was very comfortable, especially the very soft bed!! "
United States
C J.
The price is HK$875
HK$1,556 total
includes taxes & fees
14 Jul - 15 Jul
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior

Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is HK$784
HK$1,356 total
includes taxes & fees
27 Jul - 28 Jul
Maple Cozy Cabin at Lost Trails
Exterior

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison
The price is HK$917
HK$1,929 total
includes taxes & fees
13 Jul - 14 Jul
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Exterior detail

Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (28 reviews)
"Peaceful and quiet loved it "
United States
Robert V.
The price is HK$862
HK$1,455 total
includes taxes & fees
13 Jul - 14 Jul
Cedar Rustic Cabin at Lost Trails
Interior

School Days

School Days
Versailles
The price is HK$1,216
HK$1,538 total
includes taxes & fees
19 Jul - 20 Jul
School Days
Exterior

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"We had a wonderful stay! Everything was clean, communication was great - it was the perfect weekend getaway!"
United Kingdom
Karen L.
The price is HK$784
HK$1,356 total
includes taxes & fees
20 Jul - 21 Jul
Sassafras Woodland Cabin at Lost Trails
Fridge, microwave, oven, stovetop

Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.6 out of 10, Exceptional, (4 reviews)
"This is a total hidden gem! The cabin seemed brand new and was outfitted with everything you might need. We spent our 25th wedding anniversary weekend here and loved every second! Would highly recommend!"
United States
Jodi E.
The price is HK$784
HK$1,356 total
includes taxes & fees
27 Jul - 28 Jul
Mulberry Secluded Cabin at Lost Trails
Interior

Cozy River View 1BR Near Creation Museum+ Perfect North Slopes

Cozy River View 1BR Near Creation Museum+ Perfect North Slopes
Aurora
The price is HK$1,023
HK$1,787 total
includes taxes & fees
13 Jul - 14 Jul
Cozy River View 1BR Near Creation Museum+ Perfect North Slopes
Exterior

Buggy Shed

Buggy Shed
Versailles
10.0 out of 10, Exceptional, (1 review)
"Clean, pet friendly, and near the 2 state parks we wanted to see. Easy to check in and host was quick to communicate with us! We stayed at the school house and it was nice!"
United States
Ron L.
The price is HK$1,216
HK$1,538 total
includes taxes & fees
19 Jul - 20 Jul
Buggy Shed
Smart TV

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.8 out of 10, Exceptional, (44 reviews)
"It was great to have easy parking and available garage. The home was very pet and kid friendly. Super close to Hanover. Will stay here many times over in the future for visits. "
United States
Abby E.
The price is HK$910
HK$1,975 total
includes taxes & fees
20 Jul - 21 Jul
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Smart TV

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Madison
10.0 out of 10, Exceptional, (39 reviews)
"Loved the whole place and all the little touches. It was super cozy and location wise is close to everything. We will definitely be stay again. "
United States
Hannah S.
The price is HK$910
HK$1,750 total
includes taxes & fees
16 Jul - 17 Jul
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
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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Top Canaan Hotel Reviews

Hillside Inn

Hillside Inn

10/10 Excellent
"First time here. We were impressed, for the age of the hotel it is well kept and in great shape. My wife loved the balcony, we spent some time out there watching the world roll by. Breakfast was standard hotel fare, but on the good side....scrambled eggs instead of those horrible little pre-made omelets, bacon (very thin sliced, my wife's favorite hotel bacon so far), sausage links, potatoes, waffle maker, bagels, bread, rolls, cereal, a very nice selection. The kitchen people were on the ball and kept things refilled when needed. Everyone was very friendly and personable, from the desk to the breakfast people. Room was nice and clean, with a huge bed. Water pressure was good, and you didn't lose 30 minutes of your life waiting for hot water. All in all, we'd definitely stay here again and likely will as we want to do the jet boat rides which we couldn't get this trip."
Dennis 2-night trip
Posted 4 hours ago
Hillside Inn

Find out more about Canaan

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Look no further and take a look at our great range of rental properties in Canaan!

Frequently asked questions

Can I find a holiday rental in Canaan?

Yes, there are holiday rentals close to the most popular sights in Canaan, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Canaan has to offer?

Unique! Edgar Allan Poe inspired Gothic themed home in Madison: This holiday home rental outside of Canaan has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Canaan?

While exploring the area, visit family-friendly sights like Madison Railroad Station Museum, or get outside and enjoy nature at General Butler State Resort Park. Versailles State Park and Historic District are a couple of places you'll find in the wider area.

What’s a holiday rental in Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Canaan. Holiday rentals provide amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.