Vacation rentals in Canaan

4.94 out of 5 average rating, 127 reviews

Farm stay in Owenton

Vintage Camper Cabin on Beautiful Farm Near Ark

Feel refreshed when you stay in this rustic gem. This listing features a newly converted pop up camper cabin. Truly a one of a kind. Everything has been updated with all the modern amenities while still providing that rustic appeal you've been looking to experience. You'll find yourself nestled next to the woods on the ridge of our beautiful family farm. Enjoy over 200 acres by hiking our hills, pond fishing, swimming the creek, grilling some steaks all while sipping on some fine Bourbon.

4.95 out of 5 average rating, 116 reviews

Home in Versailles

School Days

Sharpen your pencils and reminisce about your childhood school days in this beautifully reconstructed schoolhouse. Built in 1879, this gorgeous property is situated just minutes from local coffee shops, locally owned restaurants, antique shops and the second largest State Park in Indiana. Be entertained with live music, museums, and other attractions by visiting three conveniently located cities. Come enjoy the modern amenities as well as the historical features this schoolhouse has to offer.

4.98 out of 5 average rating, 108 reviews

Cabin in Vevay

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.

4.96 out of 5 average rating, 207 reviews

Yurt in Madison

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.

4.98 out of 5 average rating, 719 reviews

Cabin in Madison

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

4.96 out of 5 average rating, 124 reviews

Farm stay in Glencoe

Carriage House w King bed, Lux bath, amazing views

Take in the views at this unique and tranquil getaway. This home is part of our beautiful 50-acre working farm where you can regularly see wildlife and heritage breed farm animals. And although it sits nestled on the back ridge, it is also just a short drive to many of Kentucky and Cincinnati's amazing sites. Our farm values caring for earths resources, so we have intentionally created this space with solar power, and toxic free cleaning products. (note: 2nd bed is a deluxe airmatress)

4.93 out of 5 average rating, 105 reviews

Home in Osgood

Wilmer Crash Pad: Simple home, includes breakfast

It's a simple 2 bed, 1 bath house that is perfect for short or long stays, depending on your needs. It is on a quiet, dead-end street with a relaxing vibe. The home is well-equipped with *everything* you would need for daily life. Family friendly with toys, games, etc. Blow-up mattress and futon for extra sleepers. Keyless entry. Two car detached garage. Perfect for work trips or area visits. One hour from Cincy, 75 minutes to Indy, 90 minutes to Louisville, 20 minutes to Batesville.

4.98 out of 5 average rating, 118 reviews

Apartment in Madison

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Superhost

Cottage in Madison

4.9 out of 5 average rating, 179 reviews

Cozy Farmhouse Retreat in Historic District

Located in the Historic District in Madison! Lisa and Richard co-own and co-host this recently updated cottage. Welcome to our cozy, chic Farmhouse Retreat. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings for which Madison is famous. Only three blocks from the mighty Ohio and a short five-minute drive to Clifty Falls State Park. We fell in love with Madison and know you will, too.

5 out of 5 average rating, 109 reviews

Vineyard Château - peaceful country setting!

Forget your worries in this spacious and serene space. A beautiful three bedroom home, located between two historic towns of Vevay and Madison, Indiana. Perfect location for some rest & relaxation. Private country setting, just a short drive away from antiques, restaurants, state parks, and Splinter Ridge Hunting Reserve. Please note: The home is located 13 miles east of downtown Madison, approximately a 20 minute drive.

4.96 out of 5 average rating, 124 reviews

Dome in Vevay

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, heat and air-conditioning and all the amenities. We are conveniently located within 15 miles of Madison, IN, Vevay, IN, Clifty Falls, Belterra Casino, also within 62 miles of Cincinnati and Louisville.

4.99 out of 5 average rating, 180 reviews

Cabin in Madison

Stoney Creek Cabin - Sit back and unwind

Welcome to Stoney Creek Cabin. This charming 2 bedroom cabin is nestled in the hills of Madison, IN. Situated far enough away to offer all the privacy you want, yet only 8 miles from historic downtown, where there are so many gems nearby to explore. Enjoy the HOT TUB, wrap around porch, and patio! There could not be a more relaxing place to unwind.

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Other great vacation rentals in Canaan

4.89 out of 5 average rating, 36 reviews

Apartment in Aurora

Family-friendly 2BR Hot Tub & Pool

andrewRating, 5 stars1 week ago

awesome place, close to town but secluded, pool and hot tub did not disappoint, cool layout plenty of seating, good ac, loved the projector and surround sound we watched 2 family movies and had a great time, kids loved the love sacs. As fellow hosts nice work

Superhost

Cabin in Madison

4.88 out of 5 average rating, 17 reviews

Peaceful Cozy Cabin

TyRating, 5 stars2 weeks ago

We had an amazing stay at this cozy cabin in Madison, Indiana! From the moment we arrived, everything was spotless, beautifully maintained, and thoughtfully prepared. The peaceful setting was exactly what we needed—a perfect balance of seclusion and convenience, with downtown Madison just a short drive away!

4.97 out of 5 average rating, 61 reviews

Glenda’s Overlook

AdrianRating, 5 stars3 days ago

Everything was lovely! Thank you!

5 out of 5 average rating, 44 reviews

2 King Beds-1 Block to Main St-Downtown Cottage!

KristopherRating, 5 stars1 week ago

We had a great stay at this cozy little house in Madison! The 2-bedroom space was clean, comfortable, and pet-friendly, which was perfect for our trip. It's in a great location—an easy walk to the riverfront, Main Street, and lots of great bars and restaurants. Quiet neighborhood but close to everything. Highly recommend for a relaxing and convenient stay in Madison!

4.98 out of 5 average rating, 46 reviews

Guesthouse in Warsaw

Romantic Carriage House in Historic Rivertown

JeanaRating, 5 stars2 weeks ago

we loved Lena's place. it was exactly what we were needing for a quite, peaceful weekend. We were able to walk to Jewells on main and just a 2 minute drive to Sunset Grill. Both were very good! Lenas place was very cozy, clean and so cute. We really enjoyed the place and Lena was most friendly and helpful.

5 out of 5 average rating, 81 reviews

Walnut Street Saloon BNB

SharonRating, 5 stars5 days ago

Highly recommend this rental. The location is great! We gathered for a family get together and it was spacious and comfortable. The history of the building and neighborhood was charming too. Our host made us feel very welcome.

4.97 out of 5 average rating, 519 reviews

Apartment in Madison

Dragonfly Suite

ElizabethRating, 5 stars1 week ago

Wonderful! Fantastic location for exploring Madison! Tamara was a pleasure to work with - friendly quick responses, helpful local recommendations, and flexible attitude. Amazing value for such a quiet, central, and well cared for place. Thanks so much!