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Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Canaan vacation rentals

TV, fireplace, DVD player

Cabin on the Ridge

Cabin on the Ridge
Madison
10.0 out of 10, Exceptional, (19 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
$220 nightly
The price is $253
Jul 21 - Jul 22
Total with taxes and fees
Cabin on the Ridge
TV, fireplace

Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel
Madison
10.0 out of 10, Exceptional, (20 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
$210 nightly
The price is $242
Jul 21 - Jul 22
Total with taxes and fees
Cabin on the Ridge: The Sequel
Private kitchen

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.
$173 nightly
The price is $194
Jul 21 - Jul 22
Total with taxes and fees
Charming new tiny house-Friendship IN
Terrace/patio

Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
$155 nightly
The price is $173
Jul 26 - Jul 27
Total with taxes and fees
Walnut Secluded Cabin at Lost Trails
Exterior

Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (13 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
$155 nightly
The price is $173
Jul 26 - Jul 27
Total with taxes and fees
Sassafras Woodland Cabin at Lost Trails
Exterior

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 10 - Aug 11
Total with taxes and fees
Maple Cozy Cabin at Lost Trails
Exterior detail

Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (28 reviews)
"Peaceful and quiet loved it "
United States
Robert V.
$165 nightly
The price is $185
Jul 22 - Jul 23
Total with taxes and fees
Cedar Rustic Cabin at Lost Trails
Coffee/tea maker, fridge, microwave, oven

Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.6 out of 10, Exceptional, (4 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 $173
Jul 26 - Jul 27
Total with taxes and fees
Mulberry Secluded Cabin at Lost Trails
Exterior

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison
$202 nightly
The price is $232
Jul 21 - Jul 22
Total with taxes and fees
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Interior

King Bed|Smoking|Aurora

King Bed|Smoking|Aurora
Aurora, IN
10.0 out of 10, Exceptional, (70 reviews)
"Really liked the peaceful vibe here!"
United States
Anonymous traveler
$74 nightly
The price is $83
Jul 22 - Jul 23
Total with taxes and fees
King Bed|Smoking|Aurora
Property grounds

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, (14 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.
$172 nightly
The price is $197
Aug 11 - Aug 12
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior

The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (37 reviews)
"Everything was absolutely wonderful "
United States
Michael (alex) W.
$210 nightly
The price is $242
Jul 29 - Jul 30
Total with taxes and fees
The Artist’s A-Frame
Interior

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, (1 review)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
$148 nightly
The price is $170
Jul 21 - Jul 22
Total with taxes and fees
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Smart TV

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, (68 reviews)
"We were very pleased with the location and cleanliness of the home. Comfy and cozy atmosphere and communication with owner was great! Highly recommend for a nice quiet getaway! "
United States
Julie L.
$216 nightly
The price is $248
Jul 22 - Jul 23
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Smart TV

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

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Hanover
9.8 out of 10, Exceptional, (46 reviews)
"It was great to have easy parking and available garage. The home was very pet and kid friendly. Super close to Hanover. Will stay here many times over in the future for visits. "
United States
Abby E.
$218 nightly
The price is $251
Jul 21 - Jul 22
Total with taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior

Buggy Shed

Buggy Shed
Versailles
10.0 out of 10, Exceptional, (1 review)
"Clean, pet friendly, and near the 2 state parks we wanted to see. Easy to check in and host was quick to communicate with us! We stayed at the school house and it was nice!"
United States
Ron L.
$175 nightly
The price is $196
Jul 22 - Jul 23
Total with taxes and fees
Buggy Shed
Smart TV

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, (40 reviews)
"Loved the whole place and all the little touches. It was super cozy and location wise is close to everything. We will definitely be stay again. "
United States
Hannah S.
$199 nightly
The price is $229
Jul 26 - Jul 27
Total with taxes and fees
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Property grounds

Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (5 reviews)
$132 nightly
The price is $148
Jul 29 - Jul 30
Total with taxes and fees
Briar Ridge Cabin in Osgood IN
Exterior detail

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
9.0 out of 10, Wonderful, (14 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
$152 nightly
The price is $162
Jul 26 - Jul 27
Total with taxes and fees
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Interior

School Days

School Days
Versailles
$175 nightly
The price is $196
Jul 21 - Jul 22
Total with taxes and fees
School Days
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

Riverboat Inn and Suites

Riverboat Inn and Suites

10/10 Excellent
"Excellent place and Zack was an awesome host! Made us feel right at home."
Peter 3-night trip
Posted 11 hours ago
Riverboat Inn and Suites

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 $170 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?

Unique! Edgar Allan Poe inspired Gothic themed home in Madison: Visitors like this Canaan vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.