Canaan Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Canaan Vacation Homes

Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
Exterior detail

Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

9.8 out of 10, Exceptional, (39)
"House was clean and cozy, great weekend getaway place. "
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Fridge, microwave, oven, stovetop

The Wee House is a shotgun house that is remodeled with a view of the Ohio river

9.6 out of 10, Exceptional, (50)
"Fantastic location-Ohio River View; walkable to Madison’s downtown, river walk, and bridge."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Fridge, microwave, oven, stovetop

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

9.8 out of 10, Exceptional, (36)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is CA $172
CA $342 total
includes taxes & fees
Aug 24 - Aug 25
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Fridge, microwave, oven, stovetop

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

10.0 out of 10, Exceptional, (7)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Madison's Only YURT Experience
Dining

Madison's Only YURT Experience

9.4 out of 10, Exceptional, (8)
"Better than we expected! Lots of land for the kids to explore. The goats were so fun to watch. Fishing at the pond was a nice surprise. We loved the bottle of wine waiting for us! It was such a unique getaway! Great family trip!"
Madison's Only YURT Experience
"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub
Fridge, microwave, oven, stovetop

"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub

10.0 out of 10, Exceptional, (8)
"We thought the house was great and the location was perfect! We would definitely stay there again. "
The price is CA $191
CA $473 total
includes taxes & fees
Aug 11 - Aug 12
"Madison Manor II" by The River: Regatta Special! Patio-Fire Pit, Grill, Hot Tub
Charming 2-bedroom house in Devil's Elbow Osgood, IN
Smart TV

Charming 2-bedroom house in Devil's Elbow Osgood, IN

10.0 out of 10, Exceptional, (2)
"House is as pictured and stated. Beds were comfortable, well stocked kitchen, nice keurig selection of coffee, beautiful outdoor setting behind house backs up to woods,very peaceful. Great place would stay again."
Charming 2-bedroom house in Devil's Elbow Osgood, IN
Bungalow on Main!!
Exterior

Bungalow on Main!!

9.8 out of 10, Exceptional, (15)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!
The Wadsworth in National Historic District of Madison, Indiana.
Fridge, microwave, oven, stovetop

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (51)
"Wonderful VRBO steps away from the Ohio River and historic Madison in a very quiet setting. The home is comfortable, clean and very well-equipped, and the seating at the rear of the house is a nice bonus! The owners are great people, and have anticipated every need for a short or long stay. Highly recommend this property!"
The Wadsworth in National Historic District of Madison, Indiana.
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
Outdoor dining

"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit

9.4 out of 10, Exceptional, (8)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
The price is CA $191
CA $473 total
includes taxes & fees
Aug 11 - Aug 12
"Madison Manor I" by The River: Nice patio, hot tub, gas grill, and fire pit
Never Too Far Spacious house on dead end road with great outdoor space!
Terrace/patio

Never Too Far Spacious house on dead end road with great outdoor space!

10.0 out of 10, Exceptional, (24)
"The house stay was great and very comfortable and clean, which we appreciated very much!Wld definitely recommend staying here."
The price is CA $196
CA $426 total
includes taxes & fees
Aug 11 - Aug 12
Never Too Far Spacious house on dead end road with great outdoor space!
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Outdoor spa tub

Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11

10.0 out of 10, Exceptional, (45)
"It was perfect for our group of 7. "
The price is CA $269
CA $688 total
includes taxes & fees
Aug 13 - Aug 14
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Fridge, microwave, oven, stovetop

Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

10.0 out of 10, Exceptional, (53)
"Awesome home in a great location! Very well done inside with unique features and lots of room. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Red comfy cottage
Outdoor dining

Red comfy cottage

10.0 out of 10, Exceptional, (75)
"House is very nice and clean. A bit of an odd location but that does not take away from the overall experience. This is an excellent place to stay if visiting madison."
Red comfy cottage
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
Exterior

Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!

Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
Secluded Country Home in Historic Hoosier Hills
Outdoor dining

Secluded Country Home in Historic Hoosier Hills

10.0 out of 10, Exceptional, (118)
"Great property, very peaceful. "
Secluded Country Home in Historic Hoosier Hills
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!
Fridge, microwave, oven, stovetop

Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!

10.0 out of 10, Exceptional, (24)
"Great place. "
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Fridge, microwave, oven, stovetop

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

10.0 out of 10, Exceptional, (5)
"My husband and I came to celebrate our anniversary and his retirement and to go hiking- our favorite activity together! This place was perfect! Location! Location! Location! Near everything- walked downtown to shops and restaurants! The place itself was clean, nicely decorated, and very welcoming We will e back! "
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
The Artist’s A-Frame
Exterior

The Artist’s A-Frame

10.0 out of 10, Exceptional, (15)
"Stayed for the weekend to hike at Clifty Falls. Great location to the state park and downtown restaurants. Really pretty house with everything you’d need for a stay. Host was super nice to interact with as well. Thanks again! "
The price is CA $160
CA $318 total
includes taxes & fees
Aug 12 - Aug 13
The Artist’s A-Frame
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
Property grounds

The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!

10.0 out of 10, Exceptional, (42)
"Prefect accommodations for a weekend getaway. A beautiful space, friendly owners, and a private setting."
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Canaan Hotel Reviews

Ramada by Wyndham Sparta/At Speedway

Ramada by Wyndham Sparta/At Speedway

10/10 Excellent
"The staff was friendly especially Sheila. The hotel was conveniently off the hwy."
Jacquelynn 1-night trip
Posted 5 days ago
Ramada by Wyndham Sparta/At Speedway