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Canaan Vacation Rentals

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Canaan vacation rentals

TV, fireplace

1. 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.
The price is AED 444
AED 829 total
includes taxes & fees
12 Aug - 13 Aug
Cabin on the Ridge: The Sequel
TV, fireplace, DVD player

2. 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 AED 444
AED 876 total
includes taxes & fees
12 Aug - 13 Aug
Cabin on the Ridge
Private kitchen

3. 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.
The price is AED 323
AED 720 total
includes taxes & fees
12 Aug - 13 Aug
Charming new tiny house-Friendship IN
Exterior

4. 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.
The price is AED 367
AED 635 total
includes taxes & fees
13 Aug - 14 Aug
Sassafras Woodland Cabin at Lost Trails
Coffee/tea maker, fridge, microwave, oven

5. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (6 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.
The price is AED 367
AED 635 total
includes taxes & fees
16 Aug - 17 Aug
Mulberry Secluded Cabin at Lost Trails
Exterior

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.
The price is AED 367
AED 635 total
includes taxes & fees
17 Aug - 18 Aug
Maple Cozy Cabin at Lost Trails
Terrace/patio

7. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful cabin. Enjoyed our stay."
United States
Jim A.
The price is AED 367
AED 635 total
includes taxes & fees
27 Aug - 28 Aug
Walnut Secluded Cabin at Lost Trails
Exterior detail

8. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (30 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is AED 404
AED 678 total
includes taxes & fees
12 Aug - 13 Aug
Cedar Rustic Cabin at Lost Trails
Exterior

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

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison
The price is AED 430
AED 853 total
includes taxes & fees
12 Aug - 13 Aug
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Exterior detail

10. 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)
"Nicely restored building. Charming decor"
United Kingdom
Rana W.
The price is AED 246
AED 458 total
includes taxes & fees
12 Aug - 13 Aug
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
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, (15 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 AED 390
AED 706 total
includes taxes & fees
1 Sep - 2 Sep
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Exterior

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.
The price is AED 463
AED 881 total
includes taxes & fees
24 Aug - 25 Aug
The Artist’s A-Frame
Smart TV

13. 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, (44 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.
The price is AED 393
AED 782 total
includes taxes & fees
16 Aug - 17 Aug
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Interior

14. 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.
The price is AED 472
AED 610 total
includes taxes & fees
12 Aug - 13 Aug
School Days
Property grounds

15. Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 367
AED 535 total
includes taxes & fees
10 Sep - 11 Sep
Briar Ridge Cabin in Osgood IN
Smart TV

16. 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, (71 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.
The price is AED 413
AED 860 total
includes taxes & fees
23 Aug - 24 Aug
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Interior

17. 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
The price is AED 272
AED 305 total
includes taxes & fees
24 Aug - 25 Aug
King Bed|Non-Smoking
Interior

18. 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.
The price is AED 354
AED 660 total
includes taxes & fees
25 Aug - 26 Aug
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Smart TV

19. 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
9.6 out of 10, Exceptional, (48 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.
The price is AED 426
AED 925 total
includes taxes & fees
19 Aug - 20 Aug
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Pool

20. #207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown
Madison
10.0 out of 10, Exceptional, (43 reviews)
"Loved this place, very clean and well stocked with the little extras that you always seem to need. "
United States
Matt C.
#207 King Suites, River Views, Deck, Downtown
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

Empire House Hotel

Empire House Hotel

10/10 Excellent
"A very historic house that has a great view of the Ohio River. It is very dated, but very quiet and relaxing."
Michelle 1-night trip
Posted 2 hours ago
Empire House Hotel

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 Sunrise Falls Golf Course 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.