Vacation Homes in Jefferson County

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Featured Vacation Homes in Jefferson County

Fridge, microwave, oven, stovetop
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE

Holiday Home in Pendleton

9.8 out of 10, Exceptional, (62)
"Came to the area for a funeral. Worked out great for our needs. Alecia was quick to respond any time we called. Enjoyed it. "
United Kingdom
Clyde C.
The price is HK$685
HK$1,819 total
includes taxes & fees
13 Dec - 14 Dec
RETREAT TO HORSE COUNTRY & STAY IN THE ADORABLE PRIVATE TACK HOUSE
Outdoor spa tub
Spectacular waterfront house!

Holiday Home in Prospect

9.6 out of 10, Exceptional, (86)
"Great location with views of the river. "
United States
Patrick G.
Spectacular waterfront house!
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Holiday Home in Madison

9.8 out of 10, Exceptional, (51)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is HK$973
HK$1,943 total
includes taxes & fees
8 Dec - 9 Dec
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior
Cozy Tiny House in Scottsburg

Holiday Home in Scottsburg

9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is HK$615
HK$1,343 total
includes taxes & fees
29 Dec - 30 Dec
Cozy Tiny House in Scottsburg
Dining
Madison's Only YURT Experience

Holiday Home in Madison

9.2 out of 10, Wonderful, (11)
"One if the most relaxing vacations that I have ever had. Very private, quiet and no traffic. The bed was very comfortable the space of the entire yurt was amazing. My little dogs loved the goats, and running lease free. We were not looking forward to leaving. The host is wonderful too!! We highly recommend staying here!!"
United States
Sharon N.
Madison's Only YURT Experience
Outdoor dining
Red comfy cottage

Holiday Home in Madison

10.0 out of 10, Exceptional, (83)
"Very nice property. The air worked great in the heat and loved the hot tub at nights"
United States
Jared S.
Red comfy cottage
Fridge, microwave, oven, stovetop
Country home with beautiful views and access to hiking, biking, and horse trails

Holiday Home in Henryville

10.0 out of 10, Exceptional, (28)
"Nice peaceful place quiet and just what we was looking for"
United States
Cruze B.
The price is HK$1,156
HK$1,931 total
includes taxes & fees
8 Dec - 9 Dec
Country home with beautiful views and access to hiking, biking, and horse trails
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Holiday Home in Hanover

9.8 out of 10, Exceptional, (33)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is HK$904
HK$1,962 total
includes taxes & fees
8 Dec - 9 Dec
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Dining
Enchanting, energizing, and enjoyable!

Holiday Home in Buckner

10.0 out of 10, Exceptional, (92)
"Everything was just as advertised and more the amenities and the house were outstanding!!!!"
United States
Alex K.
Enchanting, energizing, and enjoyable!
2 bedrooms, WiFi, bed sheets
Maple Cabin at Lost Trails

Holiday Home in Madison Township

10.0 out of 10, Exceptional, (5)
"This new cabin was clean, in nature. Great communication with host."
United States
Hamilton
Maple Cabin at Lost Trails
Exterior
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!

Holiday Home in Madison

10.0 out of 10, Exceptional, (1)
"Cozy, fun get away close to downtown yet secluded enough to feel like you had privacy. "
United States
Raena E.
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!
Property grounds
The Norton Commons Lavish

Holiday Home in Louisville

10.0 out of 10, Exceptional, (9)
"Great location in a great neighborhood."
United States
Steve O.
The Norton Commons Lavish
Terrace/patio
Family/Pet-Friendly Riverside Home w/Amazing Views

Holiday Home in Prospect

9.0 out of 10, Wonderful, (22)
"This was our second stay at the River house. We had a great stay!! I Love the view from the deck!! "
United States
Rachel R.
Family/Pet-Friendly Riverside Home w/Amazing Views
Exterior
Charming 3-bedroom house in lovely downtown Madison.

Holiday Home in Madison

2.0 star property
9.4 out of 10, Exceptional, (11)
"Great old home and cool neighborhood. "
United States
Randy S.
Charming 3-bedroom house in lovely downtown Madison.
Dining
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Holiday Home in Madison

9.6 out of 10, Exceptional, (24)
"Very nice house good accommodations would stay again !!!"
United States
Henry C.
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath
Interior
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC

Holiday Home in Charlestown

10.0 out of 10, Exceptional, (12)
"The property was clean and quiet. Great location in a nice residential neighborhood. Very close to Charlestown State Park where we did some hiking."
United States
Chris S.
The price is HK$740
HK$1,144 total
includes taxes & fees
8 Dec - 9 Dec
Charming 1-bedroom carriage house in delightful Charlestown with WiFi, AC
Private kitchen
Auralis: Sleeps 8

Holiday Home in Madison

10.0 out of 10, Exceptional, (2)
"Amazing place!"
United States
Al B.
Auralis: Sleeps 8
Fridge, microwave, oven, stovetop
The Wadsworth in National Historic District of Madison, Indiana.

Holiday Home in Madison

10.0 out of 10, Exceptional, (62)
"We had a lovely stay here in Madison. This is an excellent VRBO. We will definitely visit again. "
United States
Rebecca W.
The Wadsworth in National Historic District of Madison, Indiana.
Interior
Relaxing Country Getaway

Holiday Home in Lexington

9.4 out of 10, Exceptional, (43)
"Very nice. We enjoyed ourselves a lot and would come back! "
United States
Stephanie G.
Relaxing Country Getaway
Outdoor pool
KY log home close to The Ark Encounter on private 14 acres private seasonal pool

Holiday Home in Ghent

9.2 out of 10, Wonderful, (30)
"We enjoyed our stay. The property would be great for a big family stay. It was just us 4 and we all slept upstairs. I don’t have any complaints but we wish the pond was without algae and moss. Thanks for a great weekend!"
United States
Kayla D.
KY log home close to The Ark Encounter on private 14 acres private seasonal pool
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Jefferson County Hotel Reviews

Hillside Inn

Hillside Inn

10/10 Excellent
"Very nice view of the river and downtown, staff is very friendly nice older place with very reasonable prices "
Dustin 1-night trip
Posted 2 days ago
Hillside Inn

Find out more about Jefferson County

Jefferson County Vacation Homes information

Number of reviews
654
Accommodation
122 Vacation Homes
Lowest Price
HK$1,144
Highest Price
HK$1,962