Jefferson County Holiday Rentals

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Featured Jefferson County Holiday Rentals

Property grounds
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Madison
9.8 out of 10, Exceptional, (10)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
United States
Courtney G.
The price is HK$592
HK$1,004 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Exterior
Cabin on the Ridge: The Sequel

Cabin on the Ridge: The Sequel

Madison
10.0 out of 10, Exceptional, (17)
"This was an excellent property and had everything we needed for a relaxing girls night!!! The cabin was very clean and in a quiet, secluded area which was perfect for enjoying nature!!!"
United States
Samantha B.
The price is HK$872
HK$1,629 total
includes taxes & fees
8 Dec - 9 Dec
Cabin on the Ridge: The Sequel
Exterior detail
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

2.0 star property
Madison
The price is HK$617
HK$1,246 total
includes taxes & fees
14 Dec - 15 Dec
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
TV, fireplace, DVD player
Cabin on the Ridge Su

Cabin on the Ridge Su

Madison
10.0 out of 10, Exceptional, (15)
"Peaceful relaxing stay. Will go back."
United States
Wendy P.
The price is HK$872
HK$1,817 total
includes taxes & fees
10 Dec - 11 Dec
Cabin on the Ridge Su
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
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
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
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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

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!
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
"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
Modern Nature Cabin | Private Escape in the Forest

Modern Nature Cabin | Private Escape in the Forest

Hanover
9.8 out of 10, Exceptional, (7)
"Very nice facility and relaxing setting . "
United States
Robert V.
The price is HK$723
HK$1,748 total
includes taxes & fees
11 Dec - 12 Dec
Modern Nature Cabin | Private Escape in the Forest
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
Outdoor dining
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

Madison
9.6 out of 10, Exceptional, (12)
"We thoroughly enjoyed our time! Great place! We would definitely stay there again!"
United States
Howard B.
The price is HK$1,253
HK$2,838 total
includes taxes & fees
9 Dec - 10 Dec
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour
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
1 bedroom, WiFi, bed sheets
East Main Lofts - Boho 203

East Main Lofts - Boho 203

Madison
9.6 out of 10, Exceptional, (8)
"Very tasteful loft in convenient location. Enjoyed our stay."
United States
Teresa P.
The price is HK$1,534
HK$2,713 total
includes taxes & fees
21 Dec - 22 Dec
East Main Lofts - Boho 203
Interior
#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown

Madison
10.0 out of 10, Exceptional, (36)
"This is a beautiful historic house. Everything was neat, clean and perfect working order. Will definitely stay there again."
United States
Rick M.
The price is HK$1,549
HK$3,361 total
includes taxes & fees
8 Dec - 9 Dec
#207 King Suites, River Views, Deck, Downtown
Fridge, microwave, oven, stovetop
#209 Kings, River View, Deck, Bicentennial Park

#209 Kings, River View, Deck, Bicentennial Park

Madison
10.0 out of 10, Exceptional, (62)
"Amazing stay in an beautiful town. Easy access to charming shops and restaurants. "
United States
Kyle L.
#209 Kings, River View, Deck, Bicentennial Park
Microwave, oven, stovetop, dishwasher
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

Hanover
9.0 out of 10, Wonderful, (4)
"The Hanover House was very large, nicely furnished and the sunrise and sunsets were beautiful. A perfect getaway for a group of friends. Plenty of room to spread out and play games. Very relaxing, close to restaurants, shopping and site seeing. The host was extremely friendly and very helpful and quick to respond. We would definitely stay there again!!!"
United States
Deborah D.
The price is HK$1,541
HK$3,635 total
includes taxes & fees
8 Dec - 9 Dec
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison
Terrace/patio
Madison Manor By the River: Sleeps up to 15, Walk to Historic Downtown

Madison Manor By the River: Sleeps up to 15, Walk to Historic Downtown

2.0 star property
Madison
Madison Manor By the River: Sleeps up to 15, Walk to Historic Downtown
4 bedrooms
East Main Lofts -Roller Rink 301

East Main Lofts -Roller Rink 301

Madison
10.0 out of 10, Exceptional, (7)
"Nice place in the Heart of downtown. Clean open space design with plenty of room for a large group."
United States
David T.
The price is HK$4,252
HK$7,630 total
includes taxes & fees
8 Dec - 9 Dec
East Main Lofts -Roller Rink 301
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