Jefferson County Holiday Rentals

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Featured Jefferson County Holiday Rentals

4 bedrooms, free WiFi, bed sheets
Rustic cabin just outside of Madison!

Rustic cabin just outside of Madison!

Madison
10.0 out of 10, Exceptional, (53)
"Great day, we loved the cabin!"
United States
Mark C.
Rustic cabin just outside of Madison!
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Madison
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is HK$666
HK$1,437 total
includes taxes & fees
8 Dec - 9 Dec
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

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

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 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
Madison
10.0 out of 10, Exceptional, (14)
"Great little place. Location was exceptional. "
United States
Andrew P.
The price is HK$981
HK$1,307 total
includes taxes & fees
8 Dec - 9 Dec
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Exterior
Sleeps 4, Rustic, Secluded

Sleeps 4, Rustic, Secluded

Lexington
8.0 out of 10, Very good, (4)
"The cabin and property were very clean and easy to find. We loved the back yard for chilling around after we got back from the event we were attending. Host was very friendly and had good communication. Will stay again if we are back in the area! "
United States
Nicole C.
The price is HK$852
HK$1,777 total
includes taxes & fees
8 Dec - 9 Dec
Sleeps 4, Rustic, Secluded
Interior
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Madison
10.0 out of 10, Exceptional, (61)
"This was the best place I have ever stayed. The place was amazing and the hospitality exceeded expectations. I would definitely recommend staying here. "
United States
Adam K.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
1 bedroom, WiFi, bed sheets
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

Madison
8.8 out of 10, Excellent, (10)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is HK$649
HK$1,108 total
includes taxes & fees
5 Jan - 6 Jan 2026
Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Microwave, oven, stovetop
Charming 2-bedroom house with a river view in wonderful Madison

Charming 2-bedroom house with a river view in wonderful Madison

2.0 star property
Madison
10.0 out of 10, Exceptional, (1)
"Great spot walkable to downtown Madison & the river area. Appreciated how well-stocked the kitchen, bathroom, and laundry were. And being able to bring a pet was a big plus."
United States
Chelsea C.
Charming 2-bedroom house with a river view in wonderful Madison
Exterior
Charming 3-bedroom house in lovely downtown Madison.

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
Madison
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.
Interior
Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind

Madison
10.0 out of 10, Exceptional, (102)
"Close enough to be convenient to local attractions, out enough to be mostly quiet. "
United States
Garry B.
Stoney Creek - Sit back and unwind
Fridge, microwave, oven, stovetop
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

Madison
10.0 out of 10, Exceptional, (12)
"Madison Manor II was perfect for our annual girls trip. We were comfortable, location was great, the home was very clean."
United States
Carissa N.
The price is HK$1,183
HK$2,811 total
includes taxes & fees
8 Dec - 9 Dec
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill
Fridge, microwave, oven, stovetop
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

Madison
9.6 out of 10, Exceptional, (20)
"My wife and I enjoyed our stay here while checking out Madison. Great location, nicely decorated. "
United States
Justin L.
The price is HK$1,401
HK$2,256 total
includes taxes & fees
8 Dec - 9 Dec
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison
Property grounds
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Madison
10.0 out of 10, Exceptional, (209)
"Francine's Cabin is such a peaceful and private place to stay. We love it and have stayed there several times. "
United States
Tammy C.
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Exterior
Rhythm & Blues! Quiet, private, downtown! -Golf Cart Available!

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

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!
Outdoor dining
Red comfy cottage

Red comfy cottage

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
Exterior
The Artist’s A-Frame

The Artist’s A-Frame

Madison
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is HK$981
HK$1,898 total
includes taxes & fees
18 Dec - 19 Dec
The Artist’s A-Frame
Interior
Sunset over the city Suite 201, Sunset over the city Suite 201

Sunset over the city Suite 201, Sunset over the city Suite 201

Madison
9.6 out of 10, Exceptional, (13)
"Quick and easy one night stay. Comfy bed. Didn’t use much in the space but seemed well stocked. Clean and cozy property. Will definitely stay here again. "
United States
Christy H.
The price is HK$677
HK$1,137 total
includes taxes & fees
22 Dec - 23 Dec
Sunset over the city Suite 201, Sunset over the city Suite 201
Fridge, microwave, oven, stovetop
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

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

Madison
10.0 out of 10, Exceptional, (17)
"Perfect location for a long weekend getaway! Cute place and right on the river. Place was clean and cozy, host was great. "
United States
Toni N.
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Dining
Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

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
1 bedroom
Historic city overlook suite 206, Historic city overlook suite 306

Historic city overlook suite 206, Historic city overlook suite 306

Madison
9.2 out of 10, Wonderful, (10)
"Very clean and cozy! Nice area close to town. "
United States
Susan C.
Historic city overlook suite 206, Historic city overlook suite 306
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.
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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