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Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

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, (21 reviews)
"Our stay was amazing! Loved this cozy cabin in the woods! "
United States
Alison F.
The price is ￥19,087
￥36,462 total
includes taxes & fees
Aug 9 - Aug 10
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, (19 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is ￥19,087
￥38,457 total
includes taxes & fees
Aug 10 - Aug 11
Cabin on the Ridge
Terrace/patio

3. 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 ￥15,767
￥27,277 total
includes taxes & fees
Sep 3 - Sep 4
Walnut Secluded Cabin at Lost Trails
Private kitchen

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.
The price is ￥13,875
￥30,550 total
includes taxes & fees
Aug 19 - Aug 20
Charming new tiny house-Friendship IN
Exterior

5. 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 ￥15,767
￥27,277 total
includes taxes & fees
Aug 10 - Aug 11
Maple Cozy Cabin at Lost Trails
Exterior

6. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (14 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is ￥15,767
￥27,277 total
includes taxes & fees
Aug 11 - Aug 12
Sassafras Woodland Cabin at Lost Trails
Coffee/tea maker, fridge, microwave, oven

7. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.6 out of 10, Exceptional, (5 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 ￥15,767
￥27,277 total
includes taxes & fees
Aug 18 - Aug 19
Mulberry Secluded Cabin at Lost Trails
Exterior

8. 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 ￥18,447
￥36,626 total
includes taxes & fees
Aug 13 - Aug 14
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Exterior

9. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (38 reviews)
"Everything was absolutely wonderful "
United States
Michael (alex) W.
The price is ￥19,866
￥38,440 total
includes taxes & fees
Aug 10 - Aug 11
The Artist’s A-Frame
Smart TV

10. 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 ￥18,305
￥39,546 total
includes taxes & fees
Aug 16 - Aug 17
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown 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, (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.
The price is ￥16,886
￥30,480 total
includes taxes & fees
Sep 1 - Sep 2
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Property grounds

12. Briar Ridge Cabin in Osgood IN

Briar Ridge Cabin in Osgood IN
Osgood
10.0 out of 10, Exceptional, (5 reviews)
The price is ￥18,920
￥26,488 total
includes taxes & fees
Aug 25 - Aug 26
Briar Ridge Cabin in Osgood IN
Exterior detail

13. 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 ￥10,556
￥19,652 total
includes taxes & fees
Aug 12 - Aug 13
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Smart TV

14. 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)
"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.
The price is ￥17,738
￥35,812 total
includes taxes & fees
Aug 30 - Aug 31
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Interior

15. 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 ￥11,674
￥13,075 total
includes taxes & fees
Aug 22 - Aug 23
King Bed|Non-Smoking
Interior

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
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is ￥15,326
￥28,504 total
includes taxes & fees
Sep 1 - Sep 2
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Terrace/patio

17. "Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison
10.0 out of 10, Exceptional, (20 reviews)
"we had a good time. enjoyed our visit"
United States
Douglas S.
The price is ￥21,492
￥57,368 total
includes taxes & fees
Aug 24 - Aug 25
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Exterior

18. 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.
The price is ￥24,463
￥31,284 total
includes taxes & fees
Sep 1 - Sep 2
Buggy Shed
Microwave, oven, stovetop, dishwasher

19. The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St

The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Madison
9.8 out of 10, Exceptional, (23 reviews)
"This was a beautiful home and family friendly. "
United States
Cinda A.
The price is ￥21,153
￥75,119 total
includes taxes & fees
Aug 16 - Aug 17
The Main Stay - Steps from Ohio River, Shopping, & Dining on Main St
Smart TV

20. 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.
The price is ￥18,763
￥35,358 total
includes taxes & fees
Aug 11 - Aug 12
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
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

The Chandler Hotel

The Chandler Hotel

10/10 Excellent
"Such a beautiful boutique hotel in the middle of downtown Madison! It was the perfect space and loved it!"
Nicole 2-night trip
Posted 8 hours ago
The Chandler Hotel

Find out more about Canaan

Search for holiday rentals in Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in Canaan using one of the methods below:

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Look no further and take a look at our great range of rental properties in Canaan!

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.