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Canaan Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (23 reviews)
"Super nice and cute! Would definitely stay again! "
United States
Angela G.
The price is CA $183
CA $333 total
includes taxes & fees
Nov 10 - Nov 11
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, (23 reviews)
"Beautiful, clean, serene! Perfect place for a weekend anniversary getaway!"
United States
Mallory T.
The price is CA $215
CA $359 total
includes taxes & fees
Nov 24 - Nov 25
Cabin on the Ridge: The Sequel
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.
The price is CA $123
CA $258 total
includes taxes & fees
Nov 9 - Nov 10
Charming new tiny house-Friendship IN
A log cabin with a covered porch, wooden rocking chairs, and a potted plant.

4. Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind
Madison
10.0 out of 10, Exceptional, (134 reviews)
"Our family enjoyed our stay."
United States
Shanna S.
The price is CA $175
CA $335 total
includes taxes & fees
Nov 15 - Nov 16
Stoney Creek - Sit back and unwind
A wooden cabin with a porch, a staircase, and a deck.

5. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (20 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is CA $141
CA $241 total
includes taxes & fees
Dec 6 - Dec 7
Sassafras Woodland Cabin at Lost Trails
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

6. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (32 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is CA $154
CA $245 total
includes taxes & fees
Nov 29 - Nov 30
Cedar Rustic Cabin at Lost Trails
2

7. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (16 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 CA $140
CA $239 total
includes taxes & fees
Nov 30 - Dec 1
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.

8. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"We loved the cabin, it had everything we needed - lovely peaceful surroundings, and was very clean! Thank you."
United States
Lisa S.
The price is CA $140
CA $239 total
includes taxes & fees
Nov 22 - Nov 23
Mulberry Secluded Cabin at Lost Trails
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

9. 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.
The price is CA $140
CA $239 total
includes taxes & fees
Nov 29 - Nov 30
Walnut Secluded Cabin at Lost Trails
A hot tub with candles, a fire feature, and a tent in a forested area.

10. 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.
The price is CA $224
CA $339 total
includes taxes & fees
Nov 9 - Nov 10
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.

11. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Great experience. Definitely recommend staying here if you’re visiting Madison. Great location to down town,"
United States
Mike H.
The price is CA $191
CA $346 total
includes taxes & fees
Nov 8 - Nov 9
The Artist’s A-Frame
A covered deck with a wooden table and wicker chairs, overlooking a lake.

12. The River View at Esther’s

The River View at Esther’s
Vevay
10.0 out of 10, Exceptional, (2 reviews)
"This is a beautiful property and lovely house. We really enjoyed the back deck and the chairs by the river. It was nice having an enclosed yard space for our dog. The coffee station was well stocked and loved the flavored Crave pods! The bed was also very comfortable. We saw some eagles diving at possibly a muskrat. The host was quickly responsive when we reached out for a very minor issue. Thank you for a wonderful stay. Shari and Jim"
United States
James F.
The price is CA $157
CA $290 total
includes taxes & fees
Nov 7 - Nov 8
The River View at Esther’s
A rustic interior with a wooden staircase, stone walls, and a dining area with chairs and a table.

13. 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 CA $250
CA $291 total
includes taxes & fees
Nov 8 - Nov 9
School Days
A dining area with a view of a bridge over a river, a table set with plates and cutlery, and a potted plant on the windowsill.

14. Downtown Riverfront Cottage

Downtown Riverfront Cottage
Madison Historic District
10.0 out of 10, Exceptional, (2 reviews)
"House was very nice, very clean. The view of the river was magnificent. Next little getaway we would return again"
United States
Curtis M.
The price is CA $296
CA $501 total
includes taxes & fees
Nov 8 - Nov 9
Downtown Riverfront Cottage
A cozy room with a bed, a chair, a sofa, and a small table.

15. 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, (9 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is CA $131
CA $234 total
includes taxes & fees
Nov 11 - Nov 12
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Property grounds

16. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.4 out of 10, Exceptional, (20 reviews)
"Clean and cozy"
United States
Julie
The price is CA $125
CA $215 total
includes taxes & fees
Nov 30 - Dec 1
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

17. 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
9.2 out of 10, Wonderful, (15 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is CA $86
CA $154 total
includes taxes & fees
Nov 19 - Nov 20
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A modern living room with a fireplace, a flat-screen TV mounted above it, and a staircase with wooden steps.

18. NEW! Historic, Walk to Main St, King Suites, Patio

NEW! Historic, Walk to Main St, King Suites, Patio
Madison Historic District
10.0 out of 10, Exceptional, (1 review)
"Great property and a lot of room which was great."
United States
Kathryn B.
The price is CA $207
CA $420 total
includes taxes & fees
Nov 8 - Nov 9
NEW! Historic, Walk to Main St, King Suites, Patio
An aerial view of a swimming pool complex with multiple water slides and a surrounding area with lounge chairs and umbrellas.

19. 207 King Suites, River Views, Deck, Downtown

207 King Suites, River Views, Deck, Downtown
Madison Historic District
10.0 out of 10, Exceptional, (48 reviews)
"Loved this place, very clean and well stocked with the little extras that you always seem to need. "
United States
Matt C.
The price is CA $288
CA $592 total
includes taxes & fees
Nov 8 - Nov 9
207 King Suites, River Views, Deck, Downtown
A wooden interior with a dining table, chairs, a kitchen area, and a small window.

20. Unwind Haven

Unwind Haven
Versailles
8.0 out of 10, Very good, (1 review)
The price is CA $250
CA $291 total
includes taxes & fees
Nov 8 - Nov 9
Unwind Haven
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

Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

10/10 Excellent
"Very clean and orderly amazing staff"
Alfred 7-night trip
Posted 17 hours ago
Ramada by Wyndham Sparta/At Speedway

Find out more about Canaan

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Canaan. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.