Search Holiday Rentals in Canaan

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Top 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 £161
includes taxes & fees
18 Aug - 19 Aug
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 £194
includes taxes & fees
27 Aug - 28 Aug
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, (194)
"This was the second time we stayed at the cabin. Very peaceful, wonderful views, and only 25 minutes from downtown Madison. Highly recommend! "
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

The Artist’s A-Frame

10.0 out of 10, Exceptional, (17)
"Stayed for the weekend to hike at Clifty Falls. Great location to the state park and downtown restaurants. Really pretty house with everything you’d need for a stay. Host was super nice to interact with as well. Thanks again! "
The price is £169
includes taxes & fees
20 Aug - 21 Aug
The Artist’s A-Frame

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (91)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind

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

9.8 out of 10, Exceptional, (36)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is £188
includes taxes & fees
26 Aug - 27 Aug
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

9.6 out of 10, Exceptional, (50)
"Fantastic location-Ohio River View; walkable to Madison’s downtown, river walk, and bridge."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river

Sunset over the city Suite 201, Sunset over the city Suite 201

9.6 out of 10, Exceptional, (8)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is £103
includes taxes & fees
26 Aug - 27 Aug
Sunset over the city Suite 201, Sunset over the city Suite 201

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

10.0 out of 10, Exceptional, (46)
"Everything was really great...the property is beautiful...the amenities were amazing...and the owners so sweet and caring...the would answer a text message pronto...will stay again!"
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Grace Woods - Private Lake | Dock | Outdoor Space

Grace Woods - Private Lake | Dock | Outdoor Space

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

9.8 out of 10, Exceptional, (9)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

The Blue Door Place

9.8 out of 10, Exceptional, (12)
"Location was close to highway, river and Casino."
The price is £123
includes taxes & fees
19 Aug - 20 Aug
The Blue Door Place

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (41)
"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!

Madison's Only YURT Experience

9.4 out of 10, Exceptional, (8)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
Madison's Only YURT Experience

Charming 2-bedroom house in Devil's Elbow Osgood, IN

10.0 out of 10, Exceptional, (2)
"House is as pictured and stated. Beds were comfortable, well stocked kitchen, nice keurig selection of coffee, beautiful outdoor setting behind house backs up to woods,very peaceful. Great place would stay again."
Charming 2-bedroom house in Devil's Elbow Osgood, IN

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

10.0 out of 10, Exceptional, (306)
"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.

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

9.2 out of 10, Wonderful, (29)
"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

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (36)
"My small group wanted to relax in a quiet setting and Carol’s cabin was perfect. Extremely clean, well-provisioned, quiet and private with a beautiful property to stroll around. Would definitely come back!"
Carol’s Cabin in the Woods in Historic Hoosier Hills

Bungalow on Main!!

9.8 out of 10, Exceptional, (15)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (52)
"Wonderful VRBO steps away from the Ohio River and historic Madison in a very quiet setting. The home is comfortable, clean and very well-equipped, and the seating at the rear of the house is a nice bonus! The owners are great people, and have anticipated every need for a short or long stay. Highly recommend this property!"
The Wadsworth in National Historic District of Madison, Indiana.
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Canaan Hotel Reviews

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?

The Wee House is a shotgun house that is remodeled with a view of the Ohio river: This holiday home rental outside of Canaan is located on a river, and has a patio, a selection of games and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.