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Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Canaan vacation 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.
$206 nightly
The price is $232
Aug 30 - Aug 31
Total with taxes and fees
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)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
$225 nightly
The price is $254
Sep 7 - Sep 8
Total with taxes and fees
Cabin on the Ridge: The Sequel
A wooden cabin with a porch, a staircase, and a deck.

3. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
$140 nightly
The price is $156
Aug 30 - Aug 31
Total with taxes and fees
Sassafras Woodland Cabin at Lost Trails
A kitchen with white cabinets, a granite countertop, a stainless steel sink, a coffee maker, and a refrigerator.

4. Charming new tiny house-Friendship IN

Charming new tiny house-Friendship IN
Versailles
10.0 out of 10, Exceptional, (3 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.
$175 nightly
The price is $196
Aug 31 - Sep 1
Total with taxes and fees
Charming new tiny house-Friendship IN
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

5. 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.
$155 nightly
The price is $173
Aug 30 - Aug 31
Total with taxes and fees
Walnut Secluded Cabin at Lost Trails

6. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 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.
$155 nightly
The price is $173
Aug 31 - Sep 1
Total with taxes and fees
Maple Cozy Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

7. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"Mulberry Cabin at Lost Trails was great! The cabin was cozy and felt pretty private (even though the other cabins are within view). The bed was super comfy, and they did a great job making sure the cabin had everything one might need on a trip away from home. It was also very close to all things Madison, so it felt very convenient. We would definitely stay there again!"
United States
Emily I.
$155 nightly
The price is $173
Aug 30 - Aug 31
Total with taxes and fees
Mulberry Secluded Cabin at Lost Trails
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

8. 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.
$166 nightly
The price is $186
Sep 1 - Sep 2
Total with taxes and fees
Cedar Rustic Cabin at Lost Trails

9. 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)
"Very close to downtown restaurants and shopping. The trails out back were nice and relaxing to walk on. The property was quiet and relaxing. Perfect size for my wife and I and our 12 pound dog. The dog loved the trails and kept us busy on his walks."
United States
Dean
$160 nightly
The price is $184
Aug 31 - Sep 1
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

10. 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, (72 reviews)
"Great house just outside of historic Madison. Easy access to the river . Home is beautifully decorated and great place for a getaway. Many shops to visit in Madison ."
United States
John H.
$196 nightly
The price is $226
Sep 1 - Sep 2
Total with taxes and fees
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.

11. King Bed|Non-Smoking

King Bed|Non-Smoking
Aurora, IN
10.0 out of 10, Exceptional, (74 reviews)
"Four nights of peace in Aurora! Quiet location close to local attractions like the Creation Museum was really handy for us."
United States
Anonymous traveler
$97 nightly
The price is $109
Sep 2 - Sep 3
Total with taxes and fees
King Bed|Non-Smoking
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, (39 reviews)
"Very nice house and convenient to downtown, etc. If you stay here you definitely won’t be disappointed."
United States
Shirley L.
$213 nightly
The price is $240
Aug 30 - Aug 31
Total with taxes and fees
The Artist’s A-Frame

13. 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, (19 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.
$286 nightly
The price is $329
Sep 13 - Sep 14
Total with taxes and fees
Romantic Private Retreat 5 min from downtown with hot tub, firepit, grill

14. 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
$191 nightly
The price is $219
Sep 13 - Sep 14
Total with taxes and fees
Romantic 1 BR Retreat on the edge of woods with private hot tub
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

15. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison
9.8 out of 10, Exceptional, (22 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
$128 nightly
The price is $136
Sep 1 - Sep 2
Total with taxes and fees
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
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, (28 reviews)
"It was great"
United States
James H.
$160 nightly
The price is $179
Sep 1 - Sep 2
Total with taxes and fees
The Blue Door Place
A rustic interior with a wooden staircase, stone walls, and a dining area with chairs and a table.

17. School Days

School Days
Versailles
10.0 out of 10, Exceptional, (1 review)
"The Schoolhouse was a unique experience that we enjoyed very much! We were provided with anything that we would have needed for a comfortable stay. Our host communicated promptly whenever we needed. We appreciated the cleaniless of the home. We did not realize how close in proximity we would be with the other rentals on the property, but once inside, we felt like we had privacy. This would be a great stay for a couple or small family."
United States
Lora S.
$177 nightly
The price is $198
Aug 30 - Aug 31
Total with taxes and fees
School Days
A wooden deck with a 'WELCOME' sign, surrounded by trees and a path.

18. Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (7 reviews)
"A lovely accommodation! The cabin was spotless, well kept and comfortable, and the property was private and quiet. Great hosts that were very responsive and quick to help with anything. Would absolutely recommend!"
United States
Shirley Z.
$126 nightly
The price is $141
Sep 14 - Sep 15
Total with taxes and fees
Briar Ridge Cabin in Osgood IN
A covered outdoor seating area with Adirondack chairs and a fire pit, surrounded by trees and gravel.

19. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
10.0 out of 10, Exceptional, (17 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
$166 nightly
The price is $176
Aug 31 - Sep 1
Total with taxes and fees
Modern cabin very close to scenic riverfront walks
A cozy room with a bed, a chair, a sofa, and a small table.

20. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison
10.0 out of 10, Exceptional, (4 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
$150 nightly
The price is $173
Aug 31 - Sep 1
Total with taxes and fees
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
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

10/10 Excellent
"Clean; great view; friendly staff; close to downtown"
Stacy 1-night trip
Posted 10 hours ago
Hillside Inn

Find out more about Canaan

Everything you need to know about Canaan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Canaan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Canaan vacation 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 low season months. For more hustle and bustle, you may prefer to visit Canaan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Canaan rentals

At Expedia, we put the best Canaan vacation 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 vacation.

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 vacation rental in Canaan?

Yes, there are vacation rentals near popular points of interest in Canaan, or you can select a secluded option if you want a relaxing place to stay.

What's the top vacation rental that Canaan has to offer?

The Wadsworth in National Historic District of Madison, Indiana. : Visitors like this Canaan vacation home rental. It is located on a river and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

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 larger area.

What’s a vacation rental in Canaan like?

A vacation rental is a private property you can stay in for a couple of days or more in Canaan. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.