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Canaan Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Canaan holiday rentals

A spacious wooden cabin with a loft bedroom, a dining area, and a kitchen.

1. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is AU$401
includes taxes & fees
18 Oct - 19 Oct
Cabin on the Ridge
A cozy wooden cabin interior with a sofa, a dining table, and a TV.

2. Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful, clean, serene! Perfect place for a weekend anniversary getaway!"
United States
Mallory T.
The price is AU$391
includes taxes & fees
22 Oct - 23 Oct
Cabin on the Ridge: The Sequel
A kitchen with white cabinets, a granite countertop, a stainless steel sink, a coffee maker, and a refrigerator.

3. Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (4 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 AU$280
includes taxes & fees
5 Oct - 6 Oct
Charming new tiny house-Friendship IN
A log cabin with a covered porch, wooden rocking chairs, and a potted plant.

4. Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind
Madison
10.0 out of 10, Exceptional, (128 reviews)
"Very well kept and beautiful home to stay in. The hot tub, for pit, and wrap around porch were all very nice amenities."
United States
Daniel N.
The price is AU$376
includes taxes & fees
5 Oct - 6 Oct
Stoney Creek - Sit back and unwind
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

5. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 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 AU$251
includes taxes & fees
5 Oct - 6 Oct
Mulberry Secluded Cabin at Lost Trails
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6. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (14 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 AU$252
includes taxes & fees
1 Nov - 2 Nov
Maple Cozy Cabin at Lost Trails
Enjoy the stars from the private hot tub while enjoying the firepit

7. Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill

Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Such a cute little place for my husband and I to get away for my birthday weekend! The house was adorable, well stocked for daily needs and very clean! Will definitely stay here again and recommend it to others!! "
United States
Claire S.
The price is AU$460
includes taxes & fees
13 Oct - 14 Oct
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill
A wooden cabin with a porch, a staircase, and a deck.

8. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (16 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is AU$249
includes taxes & fees
1 Nov - 2 Nov
Sassafras Woodland Cabin at Lost Trails
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

9. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (31 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is AU$267
includes taxes & fees
6 Oct - 7 Oct
Cedar Rustic Cabin at Lost Trails
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

10. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is AU$251
includes taxes & fees
21 Oct - 22 Oct
Walnut Secluded Cabin at Lost Trails
Property grounds

11. 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, (17 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 AU$248
includes taxes & fees
5 Oct - 6 Oct
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A covered porch with a wooden door, potted plants, and a metal railing.

12. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (40 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
The price is AU$377
includes taxes & fees
25 Oct - 26 Oct
The Artist’s A-Frame
An outdoor patio with wicker furniture, a fire pit, and a table with candles and fruit.

13. Romantic 1 BR Retreat on the edge of woods with private hot tub

Romantic 1 BR Retreat on the edge of woods with private hot tub
Madison
10.0 out of 10, Exceptional, (1 review)
"This was a relaxing & romantic way to celebrate our 57th wedding anniversary. Everything was clean & the host very cordial. We enjoyed the rear deck with its fireplace & hot tube as as the comfortable bed & romantic tent interior."
United States
jon h.
The price is AU$319
includes taxes & fees
7 Oct - 8 Oct
Romantic 1 BR Retreat on the edge of woods with private hot tub
A wooden deck with a 'WELCOME' sign, surrounded by trees and a path.

14. Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (9 reviews)
"5 star stay forgot my fishing 🎣 😒 pole , just like being back in holler in nc"
United States
Kelsie
The price is AU$266
includes taxes & fees
8 Oct - 9 Oct
Briar Ridge Cabin in Osgood IN
A modern living room with a black sofa, a wooden coffee table, and a brick accent wall.

15. 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, (50 reviews)
"Had a very nice stay"
United States
Brad P.
The price is AU$361
includes taxes & fees
7 Oct - 8 Oct
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
A modern kitchen with a wooden countertop, black stools, and a wall-mounted TV.

16. The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (29 reviews)
"It was great"
United States
James H.
The price is AU$289
includes taxes & fees
2 Oct - 3 Oct
The Blue Door Place
An aerial view of a water park with multiple swimming pools, slides, and a large blue spiral water feature.

17. #209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park
Madison Historic District
10.0 out of 10, Exceptional, (72 reviews)
"The house was clean, comfortable, and had everything we needed. The location was great; very close to restaurants and shops on Main Street as well as the parks by the river. "
United States
Hannah M.
The price is AU$749
includes taxes & fees
4 Oct - 5 Oct
#209 Kings, River View, Deck, Bicentennial Park
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

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

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Madison
9.8 out of 10, Exceptional, (76 reviews)
"Love the stay very relaxed"
United States
Steve C.
The price is AU$335
includes taxes & fees
4 Oct - 5 Oct
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A hallway with a wooden desk, potted plants, and a window with a plant in a hanging pot.

19. 2 Queen Beds|Non Smoking

2 Queen Beds|Non Smoking
Aurora, IN
10.0 out of 10, Exceptional, (76 reviews)
"Nice little room with all the basics covered,just what we wanted for our stay!"
United States
Anonymous traveller
The price is AU$163
includes taxes & fees
4 Oct - 5 Oct
2 Queen Beds|Non Smoking
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

20. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is AU$173
includes taxes & fees
18 Oct - 19 Oct
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
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

8/10 Good
"Beautiful rooms in fabulous location. Room was in excellent condition. Balcony area on lower floor still has lovely view of Madison. Balcony light didn't work. Room had queen bed and table with 2 chairs. Outlets on radio and desk lamp. Roomy closet space. Side chair. Refrigerator but no microwave. Several clothes drawers. Nice bathroom with coffee maker on the counter that had slide in coffee packs. Complementary shampoo, sewing kit, and q-tips. Coffee maker limits use of bath counter but not a deal breaker. Staff very nice. Full breakfast offered in lower level included eggs which didnt taste all that great. Bacon, sausage, waffles. They had other items but I don't remember what they were. Nice view downstairs eating area obstructed slightly by some windows that were not clean..musty smell in lower level eating area and in main lobby was off putting and staff should have taken care off. Individual Rooms smelled great. Docked one point for the musty smell. I would stay here again."
Deborah or Ronald 1-night trip
Posted 5 hours ago
Hillside Inn

Find out more about Canaan

Everything you need to know about Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Canaan holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Canaan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Canaan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Canaan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Canaan holiday rentals we have selected for you start as low as AU$248 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Canaan rentals

At Expedia, we put the best Canaan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Canaan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Red comfy cottage : This holiday home rental outside of Canaan offers an indoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.