Holiday houses in Canaan

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Top-rated holiday rentals in Canaan

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Top Guest favourite
An historic black-and-white photograph depicts a two-story brick building with a sign reading 'Walnut St. Saloon.' In front, a horse-drawn wagon is positioned beside a man sitting on it, while another man stands by the building entrance.
Home in Madison
5 out of 5 average rating, 115 reviews

Walnut Street Saloon BNB

Step back in time to enjoy a historic tavern-turned-getaway in downtown Madison, Indiana. This spacious home, once a bustling town staple, combines rich history with modern amenities. Immerse yourself in Madison's vibrant heritage while staying just blocks away from locally owned shops, bars, and restaurants, as well as the beautiful Ohio River. It's the perfect vacation spot, whether you're here to shop, explore Clifty Falls State Park, or check out one of Madison's many festivals and events.

Top Guest favourite
A spacious living area features a large sectional sofa in a neutral gray shade. The wall is adorned with a decorative mirror and a rustic wooden accent, while warm lighting enhances the inviting atmosphere.
Apartment in Madison
5 out of 5 average rating, 323 reviews

Stablemaster’s Quarters/ Best downtown location!

Come see why the city awarded us with the “Stellar Award”, Best Place To Stay in Madison! The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, laundry room & a furnished white kitchen will all be appreciated. Yet, historic charm remains. You will soon see why the entire building has won multiple awards. Come see why US Today awarded Madison “ Best Small Town in the Midwest”.

Guest favourite
A spacious bedroom features a comfortable bed with white linens, complemented by a tufted bench at the foot. Exposed brick walls contrast with sleek modern appliances in the kitchen area, while warm wood flooring and soft lighting create a cozy ambiance.
Apartment in Aurora
4.86 out of 5 average rating, 142 reviews

Studio Apartment w/ Beautiful View!

Come and stay a while in this charming and unique studio apartment. Located in the heart of historical Aurora, IN, you can walk to all the shops, parks and restaurants! Step out onto your private patio and enjoy your view of the Ohio River! It’s the perfect romantic getaway. We are also pet friendly so if you want to bring your furry friends we are happy to host them as well, just be aware that there is a $100 fee that covers our additional cost. Just add them with your guests at checkout.

Top Guest favourite
A bubbling hot tub is positioned on a wooden deck, with a view of a gathering area featuring several white Adirondack chairs surrounding a fire pit. The background includes green trees and an expanse of open grass under a clear blue sky.
Cabin in Rising Sun
4.99 out of 5 average rating, 103 reviews

Cheerful 2 BR cabin on 48 acres with ponds/firepit

From the bubbling hot tub, take in the country air and tranquility at this breathtaking 48 acre (completely private) two bedroom, two bath cabin centrally located between the Ark and the Creation Museum. Enjoy a cup of coffee or glass of wine around the majestic firepit overlooking the rolling meadows. Enjoy pristine ponds (with LED fountains) to fish and swim. Watch deer and turkey roam the property. Hike the trails which include a frisbee golf course designed to take in the scenery.

Top Guest favourite
A light-filled dining area features a wooden table surrounded by white chairs. A blue area rug anchors the space, complemented by a chandelier above. A kitchen bar with seating is visible in the background, and large windows provide views of the surrounding trees.
Home in Bedford
4.99 out of 5 average rating, 224 reviews

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 180 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

Guest favourite
Cottage in Madison
4.86 out of 5 average rating, 173 reviews

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Sue’s Cottage is a quaint two bedroom cottage with a porch over looking the Heritage Trail of Madison. It is perfect for pets. It is a home to many species of birds and wildlife. Relax on the deck bird watching or stroll through the heritage trail & scenic railroad tracks surrounding the cottage, which leads to the river walk. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. A portion of each stay is donated to local charity.

Top Guest favourite
The cabin features a rustic exterior with wooden siding and a blue metal roof. A stone chimney is visible on one side. The surrounding area displays fallen leaves and bare trees, indicating a tranquil natural setting.
Cabin in Vevay
4.99 out of 5 average rating, 137 reviews

The Cabin

As you walk in, The Cabin wraps it's arms around you and says " Welcome home." You can feel the stress leave you as you settle in for your stay at this scenic cabin on 9.8 wooded acres. Fully furnished, spacious 1 room cabin with stone wood burning fireplace, equipped kitchen, bath with shower and twin over queen bunk bed. Refresh your mind & soul on the covered back porch overlooking the mature woods. Enjoy watching the abundant wildlife, including turkeys, deer, chipmunks and squirrels.

Top Guest favourite
A yurt is shown surrounded by expansive green grass under a clear blue sky. Contrails from passing aircraft create intersecting lines overhead, while sunlight shines brightly behind the structure, enhancing the tranquil outdoor setting.
Yurt in Madison
4.96 out of 5 average rating, 233 reviews

Madison's only Yurt experience!!!

You'll love this unique and romantic escape in the hills of southern Indiana! Located just 20 minutes from beautiful downtown Madison and Vevay. Enjoy the countryside in your very own yurt. Come relax after a hard day of shopping in downtown Madison or after a late night at Belterra casino. You will love the warm inviting boho style of decor while enjoy the beautiful sunsets from the deck. The stars look so close you could touch them from the grassy hillsides of this enchanting property.

Top Guest favourite
The cabin showcases a rustic exterior made of natural wood, featuring a welcoming front porch with wooden railings. Surrounding foliage displays autumn colors, enhancing the serene setting. A driveway leads to a garage door, while steps ascend to the main entry of the cabin.
Cabin in Madison
4.98 out of 5 average rating, 761 reviews

Cabin on the Ridge

Welcome to Cabin on the Ridge, your tranquil retreat nestled in the scenic hills of Madison, Indiana. Just 25 minutes from downtown Madison, our cabin offers a perfect blend of rustic charm and modern comfort. Madison, awarded the “Best Small Town in the Midwest” by USA Today and the Great American Main Street Award, is a must-visit. Enjoy the historic architecture, boutique shops, and delightful eats, or explore Clifty Falls State Park. •Fast wifi •Roku TV/Streaming services •Keurig

Top Guest favourite
The exterior of a charming shotgun house features a lavender-colored facade and a welcoming entrance. A small decorative plant is placed beside the steps, leading to a bright front door with a circular window above. Natural light enhances the inviting appearance.
Home in Madison
4.98 out of 5 average rating, 124 reviews

Lavender House

Newly renovated shot gun house, great location in downtown Madison Indiana. Only one block from Main Street where there is shopping and restaurants, and four blocks from the river front. Two bedrooms each with a queen size bed, one bath, fully stocked kitchen, small private backyard. Washer and dryer on site, on street parking.This property is a shotgun style home which means you walk through one bedroom to get to the next, but there is a door between.

Top Guest favourite
An inviting living area features a plush gray sofa adorned with decorative pillows. A wooden coffee table occupies the center, and a contemporary lamp stands beside a cozy chair. Light filters through the sliding glass doors, reflecting off the warm wooden floors.
Cabin in Versailles
4.98 out of 5 average rating, 157 reviews

Mamaws Cabin Hot tub, Creation Museum/ARK, Hiking

Spacious cabin (1100 sq feet) was once Mamaw's home. Sleeps 2 private and 4 more semi-private, 6 people total. Built in a primitive country style, it features a Loft bedroom that sleeps 3, an additional small bedroom that sleeps 1 and a Master Bedroom with Queen- size Sleep Number Bed. Fully functional kitchen and bath including washer/dryer. Outdoor fire-pit and hot tub. ROKU TV/ DVDs, No cable. Wii gaming system. WiFi available.

Top Guest favourite
Dome in Vevay
4.97 out of 5 average rating, 203 reviews

Hilltop Dome, 42 secluded acres in nature

Our Geodome is tucked away on 42 private acres exclusively for you and your guest Enjoy the stars at night, fire pit, hot tub, high speed internet, washer dryer, and smart TV . The Dome is equipped with a 2 ton mini split that will keep you warm in the winter and cool in the summer We are conveniently located within 15 miles of Madison, IN, Vevay, IN, Clifty Falls, Belterra Casino, also within 62 miles of Cincinnati and Louisville.

Popular amenities for Canaan holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Jefferson County
  5. Canaan