Canaan Holiday Rentals

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Holiday Rentals in Canaan

Cabin on the Ridge Su

9.8 out of 10, Exceptional, (10)
"We had the perfect stay at this cozy and quiet cabin! It was beautifully decorated with a lot of culture hidden inside. Would definitely stay here again! "
The price is AU$342
includes taxes & fees
24 Feb - 25 Feb
Cabin on the Ridge Su

Cabin on the Ridge: The Sequel

10.0 out of 10, Exceptional, (10)
"My wife and I made a quick trip to Madison, IN, to hike and enjoy the sights. The cabin was a great place to relax at the end of the day. It was quiet, peaceful, and very clean. We enjoyed our stay! "
The price is AU$309
includes taxes & fees
23 Feb - 24 Feb
Cabin on the Ridge: The Sequel

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

10.0 out of 10, Exceptional, (180)
"Beautiful, stunning views!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (70)
"Was a beautiful cabin wonderful hot tub awesome views loved the cows "
The price is AU$358
includes taxes & fees
23 Feb - 24 Feb
Stoney Creek - Sit back and unwind

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

10.0 out of 10, Exceptional, (23)
"This place is awesome! It’s the best place to stay in Madison, IN. Well decorated and has everything you need. The host Suzie goes over and above to make sure your stay is memorable. Great location in town. We already have future dates reserved and will add more in 2025. "
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

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

9.8 out of 10, Exceptional, (22)
"Had a good time "
The price is AU$358
includes taxes & fees
23 Feb - 24 Feb
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

9.8 out of 10, Exceptional, (39)
"The space was perfect for 4 of us traveling for a girls’ trip. Location was close to all the shops and restaurants. "
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (32)
"This cabin was off the beaten path and nestled in the woods. Very nice cabin with all the amenities you could ask for. Definitely needed a 4x4 vehicle crossing the stream. It was still full of ice and snow from the recent storm. Will stay again when in the area. "
Rustic cabin just outside of Madison!

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

10.0 out of 10, Exceptional, (17)
"It was very nice"
The price is AU$486
includes taxes & fees
23 Feb - 24 Feb
Never Too Far Spacious house on dead end road with great outdoor space!

Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

10.0 out of 10, Exceptional, (42)
"The house is stunning. Very well decorated and completely outfitted for our stay. The kitchen had everything you could need. The owners were easy to communicate with and very helpful. Would highly recommended the property. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

Peacefully loving retreat! Cabin in charming Lawrenceburg.

9.8 out of 10, Exceptional, (26)
"Host is as sweet as can be! They went out of their way to help me with a surprise for my wife.Perfect for a date night at the casino steakhouse just 10 minutes away.Lovely place. Very private. We thoroughly enjoyed our stay."
The price is AU$257
includes taxes & fees
23 Feb - 24 Feb
Peacefully loving retreat! Cabin in charming Lawrenceburg.

Secluded Country Home in Historic Hoosier Hills

10.0 out of 10, Exceptional, (117)
"This was an excellent place we loved it!"
Secluded Country Home in Historic Hoosier Hills

Livery Loft: our other BEST downtown location! Award winning! Come see why.

10.0 out of 10, Exceptional, (11)
"This place. This owner. This was far beyond our expectations ! The location is beautiful. Comfortable . Spotless. Safe. There is no stone left unturned in this property. The owner, Suzie, is absolutely lovely. She makes the stay so comfortable and makes sure that you know where everything is . The town is fantastic and we had the time of our lives. Already looking forward for our next trip ! Thank you !!"
Livery Loft: our other BEST downtown location! Award winning! Come see why.

#207 King Suites, River Views, Deck, Downtown

10.0 out of 10, Exceptional, (29)
"We had a 5 couples get away for one evening and stayed in the house. A great view of the river and perfect location for walks to the shops, Park and restaurants. We plan on staying here again in the future! "
The price is AU$843
includes taxes & fees
23 Feb - 24 Feb
#207 King Suites, River Views, Deck, Downtown

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

10.0 out of 10, Exceptional, (13)
"Nice quiet neighborhood, comfortable place to be to unwind after each day of visiting my home town, family and friends. Property manager was very helpful. I will certainly consider for future trips to this area."
The price is AU$424
includes taxes & fees
23 Feb - 24 Feb
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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

9.0 out of 10, Wonderful, (16)
"Had a nice relaxing time"
Peaceful getaway centrally located just min. from Madison and Belterra casino.

Sonshine Cabin a great place to enjoy the Holidays with family or friends

10.0 out of 10, Exceptional, (288)
"This was our second time to stay at Sonshine Cabin. It is very clean! Decorated super cute and the kitchen is well appointed. Owners are great with communication, as well. We will definitely come again."
Sonshine Cabin a great place to enjoy the Holidays with family or friends

SKY Parlor sunrise and sunset views overlooking the river

9.2 out of 10, Wonderful, (7)
"Was a nice view of the riverThe parking was sketchy. Also would've been nice to know we were renting the attic in an A Frame home. "
The price is AU$266
includes taxes & fees
25 Feb - 26 Feb
SKY Parlor sunrise and sunset views overlooking the river

The Artist’s A-Frame

10.0 out of 10, Exceptional, (10)
"We were a group of three longtime friends in town for a holiday weekend together. The Artist’s A-Frame was the perfect place to retire at the end of a great day of shopping and eating. The home was clean, cozy, and well-appointed, and it was located in a lovely neighborhood. The owners were very responsive and easy to work with. Highly recommend the A-Frane! "
The price is AU$373
includes taxes & fees
2 Mar - 3 Mar
The Artist’s A-Frame

Bungalow on Main!!

9.6 out of 10, Exceptional, (7)
"Place was clean, downtown, and what pictures shown. Owner was kind and understanding. "
Bungalow on Main!!
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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Other types of properties in Canaan you may be interested in

Cabin on the Ridge Su

9.8 out of 10, Exceptional, (10)
"We had the perfect stay at this cozy and quiet cabin! It was beautifully decorated with a lot of culture hidden inside. Would definitely stay here again! "
The price is AU$342
includes taxes & fees
24 Feb - 25 Feb
Cabin on the Ridge Su

Cabin on the Ridge: The Sequel

10.0 out of 10, Exceptional, (10)
"My wife and I made a quick trip to Madison, IN, to hike and enjoy the sights. The cabin was a great place to relax at the end of the day. It was quiet, peaceful, and very clean. We enjoyed our stay! "
The price is AU$309
includes taxes & fees
23 Feb - 24 Feb
Cabin on the Ridge: The Sequel

Belterra Casino Resort

3.5 star property
8.4 out of 10, Very good, (1004)
"."
The price is AU$273
includes taxes & fees
23 Feb - 24 Feb
Belterra Casino Resort
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.

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?

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!: This holiday home rental outside of Canaan offers a patio, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Versailles State Park. Historic District and Lanier Mansion 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.