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Top Holiday Rentals in Canaan

Cabin on the Ridge: The Sequel

10.0 out of 10, Exceptional, (14)
"So beautiful and relaxing, very comfortable stay!"
The price is £174
includes taxes & fees
9 Jul - 10 Jul
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! "
The price is £173
includes taxes & fees
1 Jul - 2 Jul
Cabin on the Ridge Su

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 £186
includes taxes & fees
2 Jul - 3 Jul
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

10.0 out of 10, Exceptional, (189)
"Beautiful, stunning views!"
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

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

10.0 out of 10, Exceptional, (3)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (36)
"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!

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

9.2 out of 10, Wonderful, (26)
"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

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (86)
"We loved this cabin. Everything was perfect. We'll definitely be coming back!"
Stoney Creek - Sit back and unwind

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

9.8 out of 10, Exceptional, (46)
"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

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, (21)
"It was a nice place to stay clean comfortable and host was great."
The price is £223
includes taxes & fees
1 Jul - 2 Jul
Never Too Far Spacious house on dead end road with great outdoor space!

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

10.0 out of 10, Exceptional, (302)
"This cabin provided the perfect place for our family from out of town to stay for the holidays."
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

Bungalow on Main!!

9.6 out of 10, Exceptional, (10)
"Place was clean, downtown, and what pictures shown. Owner was kind and understanding. "
Bungalow on Main!!

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

10.0 out of 10, Exceptional, (2)
"Great one bedroom apartment! It was clean and great location for our quick getaway."
The price is £168
includes taxes & fees
20 Jul - 21 Jul
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Blue Door Place

9.8 out of 10, Exceptional, (8)
"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 £128
includes taxes & fees
1 Jul - 2 Jul
The Blue Door Place

Unique Secluded Cabin with Loft on Classified Forest

9.6 out of 10, Exceptional, (40)
"Beautiful, secluded cabin!! Loved seeing the deer each evening. If we are in this area again, we would definitely stay here!"
Unique Secluded Cabin with Loft on Classified Forest

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

10.0 out of 10, Exceptional, (22)
"The house was great! Easy to find, quiet area, great fenced in backyard, very clean place. We were glad to find it while in town for just a night."
The price is £200
includes taxes & fees
17 Jul - 18 Jul
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!

10.0 out of 10, Exceptional, (41)
"Prefect accommodations for a weekend getaway. A beautiful space, friendly owners, and a private setting."
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!

Rustic Cabin at Lost Trails

10.0 out of 10, Exceptional, (4)
"It was a great peaceful getaway for my wife and I. Quiet and clean. "
Rustic Cabin at Lost Trails

"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub

10.0 out of 10, Exceptional, (7)
"We thought the house was great and the location was perfect! We would definitely stay there again. "
"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub
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?

KY log home close to The Ark Encounter on private 14 acres private seasonal pool: This holiday home rental outside of Canaan is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.