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Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Canaan vacation rentals

A cozy wooden cabin interior with a sofa, a dining table, and a TV.

1. 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.
$210 nightly
The price is $237
Oct 25 - Oct 26
Total with taxes and fees
Cabin on the Ridge: The Sequel
A spacious wooden cabin with a loft bedroom, a dining area, and a kitchen.

2. Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (23 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
$223 nightly
The price is $251
Oct 28 - Oct 29
Total with taxes and fees
Cabin on the Ridge
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
9.8 out of 10, Exceptional, (6 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.
$173 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
Charming new tiny house-Friendship IN
A wooden cabin with a porch, a staircase, and a deck.

4. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (18 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
$142 nightly
The price is $164
Nov 9 - Nov 10
Total with taxes and fees
Sassafras Woodland Cabin at Lost Trails
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5. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (15 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 $180
Nov 18 - Nov 19
Total with taxes and fees
Maple Cozy Cabin at Lost Trails
A wooden deck with wicker furniture and a ceiling fan.

6. 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.
$155 nightly
The price is $173
Oct 26 - Oct 27
Total with taxes and fees
Cedar Rustic Cabin at Lost Trails
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

7. 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 $180
Nov 2 - Nov 3
Total with taxes and fees
Walnut Secluded Cabin at Lost Trails
A compact kitchen with wooden cabinets, a black refrigerator, a microwave, and a coffee machine on a small shelf.

8. 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.
$155 nightly
The price is $180
Oct 27 - Oct 28
Total with taxes and fees
Mulberry Secluded Cabin at Lost Trails
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

9. 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.
$112 nightly
The price is $119
Nov 16 - Nov 17
Total with taxes and fees
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A modern kitchen with a central island, white cabinetry, and a built-in microwave.

10. Charming 2-bedroom house with a river view in wonderful Madison

Charming 2-bedroom house with a river view in wonderful Madison
Madison Historic District
9.0 out of 10, Wonderful, (10 reviews)
"The place was indeed charming. The host was wonderful and available for all questions! "
United States
Amy W.
$266 nightly
The price is $306
Oct 26 - Oct 27
Total with taxes and fees
Charming 2-bedroom house with a river view in wonderful Madison
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, (18 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.
$149 nightly
The price is $171
Nov 2 - Nov 3
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A wall with a framed welcome message, a black metal rack with sunglasses, and a rack with colorful fabric items.

12. The River View at Esther’s

The River View at Esther’s
Vevay
10.0 out of 10, Exceptional, (1 review)
$195 nightly
The price is $218
Oct 31 - Nov 1
Total with taxes and fees
The River View at Esther’s
A cozy, illuminated tent-like structure with a green door, surrounded by trees and a gravel path.

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.
$243 nightly
The price is $279
Oct 25 - Oct 26
Total with taxes and fees
Romantic 1 BR Retreat on the edge of woods with private hot tub
A covered porch with a wooden door, potted plants, and a metal railing.

14. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Very cool house in a nice neighborhood. Had everything we needed and was close to anything you want to do in Madison. We will definitely stay there again!"
United States
Dean C.
$230 nightly
The price is $259
Nov 2 - Nov 3
Total with taxes and fees
The Artist’s A-Frame
A modern kitchen with a central island, bar stools, and a dining area with a patterned table.

15. 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, (78 reviews)
"The place is very clean, also convenient and close to down town. Check in and everything was very smooth! I recommend this cute little place especially for young families."
United States
Kyle A.
$192 nightly
The price is $220
Oct 26 - Oct 27
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A cozy room with a bed, a chair, a sofa, and a small table.

16. 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 Historic District
9.6 out of 10, Exceptional, (8 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
$154 nightly
The price is $177
Nov 9 - Nov 10
Total with taxes and fees
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
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.
$175 nightly
The price is $196
Oct 25 - Oct 26
Total with taxes and fees
School Days
A hallway with a wooden desk, potted plants, and a window with a plant in a hanging pot.

18. King Bed|Smoking|Aurora

King Bed|Smoking|Aurora
Aurora, IN
10.0 out of 10, Exceptional, (70 reviews)
"Made memories here during our visit to local parks nearby, definitely cozy enough for families or groups visiting together."
United States
Anonymous traveler
$78 nightly
The price is $87
Oct 23 - Oct 24
Total with taxes and fees
King Bed|Smoking|Aurora
A modern kitchen with a wooden countertop, black stools, and a wall-mounted TV.

19. The Blue Door Place

The Blue Door Place
Florence
9.8 out of 10, Exceptional, (30 reviews)
"Very clean, had everything we needed! "
United States
james w.
$164 nightly
The price is $184
Oct 26 - Oct 27
Total with taxes and fees
The Blue Door Place
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

20. The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Madison Historic District
9.8 out of 10, Exceptional, (13 reviews)
"We enjoyed our visit and would recommend to others looking for a convenient location and comfortable stay."
United States
Renee M.
$115 nightly
The price is $118
Nov 8 - Nov 9
Total with taxes and fees
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
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
"We had a great time at this sweet little hotel."
Laura 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 $143 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?

Red comfy cottage : Visitors like this Canaan vacation home rental. It offers an indoor pool, a patio, and a barbecue grill 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 a hot tub so you can immerse yourself in your vacation.

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.