Holiday Rentals in Canaan

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Check prices for these dates

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

Our top choices for Canaan holiday 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 €211
includes taxes & fees
10 Nov - 11 Nov
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 €224
includes taxes & fees
15 Nov - 16 Nov
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 €170
includes taxes & fees
9 Nov - 10 Nov
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 €216
includes taxes & fees
15 Nov - 16 Nov
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 €140
includes taxes & fees
8 Dec - 9 Dec
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 €160
includes taxes & fees
9 Nov - 10 Nov
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 €156
includes taxes & fees
29 Nov - 30 Nov
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 €156
includes taxes & fees
9 Nov - 10 Nov
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 €156
includes taxes & fees
29 Nov - 30 Nov
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 €222
includes taxes & fees
9 Nov - 10 Nov
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)
"Lovely! We really enjoyed this amazing house!"
United States
Roxann W.
The price is €216
includes taxes & fees
9 Nov - 10 Nov
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, (3 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 €188
includes taxes & fees
9 Nov - 10 Nov
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 €194
includes taxes & fees
29 Nov - 30 Nov
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 €300
includes taxes & fees
9 Nov - 10 Nov
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 €153
includes taxes & fees
9 Nov - 10 Nov
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 €148
includes taxes & fees
10 Nov - 11 Nov
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 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, (2 reviews)
"A perfect place to stay to explore the town of Madison! The location is within walking distance to everything you need."
United States
Claire Y.
The price is €272
includes taxes & fees
9 Nov - 10 Nov
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.
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 €154
includes taxes & fees
10 Nov - 11 Nov
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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Find out more about Canaan

Everything you need to know about Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Canaan holiday 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Canaan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Canaan holiday rentals we have selected for you start as low as €101 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Canaan rentals

At Expedia, we put the best Canaan holiday 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 holiday.

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 holiday rental in Canaan?

Yes, there are holiday rentals close to the most popular sights in Canaan, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Canaan has to offer?

Red comfy cottage : This holiday home rental outside of Canaan offers an indoor pool, a patio and a BBQ 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 1 hot tub so that you can immerse yourself in your holiday.

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 wider area.

What’s a holiday rental in Canaan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Canaan. Holiday rentals provide amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.