Search Vacation Homes in Canaan

    price find illustration

    Upfront pricing

    Our total price for your stay includes taxes and fees
    deals illustration

    Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key
    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

Vacation Homes in Canaan

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, (5)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
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, (35)
"Clean, comfortable home with everything needed for our stay. "
$217 nightly
The price is $250
Aug 10 - Aug 11
Total includes taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
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
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."
$273 nightly
The price is $306
Aug 7 - Aug 8
Total includes taxes and fees
Never Too Far Spacious house on dead end road with great outdoor space!
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Exterior detail

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

10.0 out of 10, Exceptional, (26)
"The house was clean, great location. Would stay again"
$218 nightly
The price is $251
Aug 7 - Aug 8
Total includes taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
East End River Retreat: Dogs Welcome!
Dining

East End River Retreat: Dogs Welcome!

10.0 out of 10, Exceptional, (8)
"We had a lovely time. Great property with easy access to everything. Our kids loved the golf cart and we appreciated the extra touches from the owners. Great little house for a stay in a great little town."
East End River Retreat: Dogs Welcome!
Grace Woods - Private Lake | Dock | Outdoor Space
Exterior

Grace Woods - Private Lake | Dock | Outdoor Space

Grace Woods - Private Lake | Dock | Outdoor Space
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.
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!!
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. "
$441 nightly
The price is $494
Aug 13 - Aug 14
Total includes taxes and fees
Riverview Home Near Creation Museum/Ark/Ski/Bikes/Cincinnati/Hot Tub-Sleeps 11
Modern Nature Cabin | Private Escape in the Forest
Fridge, microwave, oven, stovetop

Modern Nature Cabin | Private Escape in the Forest

10.0 out of 10, Exceptional, (1)
"Very nice place, the hike to the falls was pretty neat as well. Close to everything, yet still secluded. "
$212 nightly
The price is $223
Aug 10 - Aug 11
Total includes taxes and fees
Modern Nature Cabin | Private Escape in the Forest
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, (51)
"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
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!
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, (1)
"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
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, (14)
"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! "
$207 nightly
The price is $238
Aug 12 - Aug 13
Total includes taxes and fees
The Artist’s A-Frame
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
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
Microwave, oven, stovetop, dishwasher

Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!

10.0 out of 10, Exceptional, (7)
"This was such a nice place, very quiet and peaceful. The property was everything we had hoped for and the host was so nice and helpful."
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
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

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

Fairfield Inn & Suites Madison Historic Eagle Cotton Mill

10/10 Excellent
"Super clean, super staff, and super cool historic property on the National Historic Register. Highly recommend!"
C J 1-night trip
Posted 2 days ago
Fairfield Inn & Suites Madison Historic Eagle Cotton Mill