Canaan Holiday Rentals

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Holiday Rentals in Canaan

Cabin on the Ridge: The Sequel

10.0 out of 10, Exceptional, (15)
"So beautiful and relaxing, very comfortable stay!"
The price is AU$368
includes taxes & fees
23 July - 24 July
Cabin on the Ridge: The Sequel

Cabin on the Ridge Su

10.0 out of 10, Exceptional, (13)
"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! "
Cabin on the Ridge Su

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

10.0 out of 10, Exceptional, (189)
"Great getaway. View is fantastic!!! Location with plenty of privacy!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

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

9.8 out of 10, Exceptional, (30)
"Clean, comfortable home with everything needed for our stay. "
The price is AU$383
includes taxes & fees
27 July - 28 July
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

10.0 out of 10, Exceptional, (4)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (88)
"My husband and our son stayed for two nights and had a great time! The cabin was clean and just overall really nice. The hot tub was fantastic! The owners were very communicative and responsive. Overall, this made for a perfect little getaway!"
Stoney Creek - Sit back and unwind

The Wee House is a shotgun house that is remodeled with a view of the Ohio river

9.6 out of 10, Exceptional, (49)
"We loved the Wee House. It was great at the end of the day to sit on the porch, listen to the birds, and watch the barges on the river. The kitchen had everything we needed. We especially liked the quilts on the beds--so cheerful and colorful. And the location was perfect--just two short blocks from Main Street so we could walk everywhere."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (38)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!

Rustic Cabin at Lost Trails

10.0 out of 10, Exceptional, (5)
"It was a great peaceful getaway for my wife and I. Quiet and clean. "
Rustic Cabin at Lost Trails

Historic woodside view suite 205, Historic woodside view suite 205

9.4 out of 10, Exceptional, (3)
"This was perfect for my daughter and I for a quick one-day softball tourney. The apartment is extremely clean, easy to find, and comfortable. "
The price is AU$341
includes taxes & fees
14 Aug - 15 Aug
Historic woodside view suite 205, Historic woodside view suite 205

Grace Woods - Private Lake | Dock | Outdoor Space

Grace Woods - Private Lake | Dock | Outdoor Space

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

10.0 out of 10, Exceptional, (23)
"The house stay was great and very comfortable and clean, which we appreciated very much!Wld definitely recommend staying here."
The price is AU$461
includes taxes & fees
16 July - 17 July
Never Too Far Spacious house on dead end road with great outdoor space!

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

9.2 out of 10, Wonderful, (27)
"We enjoyed the space the cabin had to offer and had a great time."
KY log home close to The Ark Encounter on private 14 acres private seasonal pool

The Blue Door Place

9.6 out of 10, Exceptional, (10)
"We needed a place for a wedding nearby! The property was very nice, decorated very cute, had all the essentials & was very clean! Would definitely recommend. They even had kids toys & a swing set which was very nice for the kids!! "
The price is AU$264
includes taxes & fees
28 July - 29 July
The Blue Door Place

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

10.0 out of 10, Exceptional, (24)
"The place was very cute, clean, and comfortable. Great stay! Host was very responsive. "
The price is AU$387
includes taxes & fees
17 July - 18 July
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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

10.0 out of 10, Exceptional, (43)
"This is the second time staying at this unit. Next weekend, we are going down and staying in the upstairs loft. Looking forward. Always a great time staying with Suzie. Highly recommend."
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

East End River Retreat: Dogs Welcome!

10.0 out of 10, Exceptional, (5)
"We had a lovely time. Great property with easy access to everything. Our kids loved the golf cart and we appreciated the extra touches from the owners. Great little house for a stay in a great little town."
East End River Retreat: Dogs Welcome!

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (48)
"We absolutely loved our stay in Madison at the Wadsworth House! You couldn't ask for a nicer place to stay for a quiet get away!"
The Wadsworth in National Historic District of Madison, Indiana.

Madison's Only YURT Experience

9.0 out of 10, Wonderful, (6)
"Better than we expected! Lots of land for the kids to explore. The goats were so fun to watch. Fishing at the pond was a nice surprise. We loved the bottle of wine waiting for us! It was such a unique getaway! Great family trip!"
Madison's Only YURT Experience

Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

10.0 out of 10, Exceptional, (304)
"My family and I truly enjoyed our stay. We love coming here it has all the amenities that added to our comfort. Hosts were very accommodating which was really appreciated. "
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.
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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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 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.