Vacation Rentals in Jefferson County

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Top Cities in Jefferson County

Top Vacation Rentals in Jefferson County

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.
$126 nightly
The price is $129
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

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.
$185 nightly
The price is $213
Dec 7 - Dec 8
Total with taxes and fees
Cabin on the Ridge: The Sequel

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

2.0 star property
Madison
$139 nightly
The price is $160
Dec 7 - Dec 8
Total with taxes and fees
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cabin on the Ridge Su

Madison
10.0 out of 10, Exceptional, (15)
"Peaceful relaxing stay. Will go back."
United States
Wendy P.
$202 nightly
The price is $232
Dec 7 - Dec 8
Total with taxes and fees
Cabin on the Ridge Su

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

2.0 star property
Madison
10.0 out of 10, Exceptional, (14)
"We could not have been happier with this cute little place. Wonderful location with easy walking access to both the riverfront and all Madison had to offer with shops and dining options. We would not hesitate to stay here again!"
United States
Gary W.
$146 nightly
The price is $168
Dec 8 - Dec 9
Total with taxes and fees
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

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.
$216 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

The Artist’s A-Frame

Madison
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
$212 nightly
The price is $244
Dec 18 - Dec 19
Total with taxes and fees
The Artist’s A-Frame

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.
$218 nightly
The price is $251
Dec 7 - Dec 8
Total with taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

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.
$161 nightly
The price is $185
Dec 7 - Dec 8
Total with taxes and fees
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

"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.
$315 nightly
The price is $362
Dec 7 - Dec 8
Total with taxes and fees
"Madison Manor II" by The River: Hot Tub, Patio, FirePit, Grill

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.
$204 nightly
The price is $219
Jan 5 - Jan 6, 2026
Total with taxes and fees
Modern Nature Cabin | Private Escape in the Forest

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.
$224 nightly
The price is $228
Dec 8 - Dec 9
Total with taxes and fees
Sleeps 4, Rustic, Secluded

"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.
$326 nightly
The price is $375
Dec 7 - Dec 8
Total with taxes and fees
"Madison Manor I" By the River - Special Dec 6 - Tickets to Christmas Homes Tour

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.
$251 nightly
The price is $289
Dec 7 - Dec 8
Total with taxes and fees
Peaceful Cozy Cabin 10 minutes from Historic downtown Madison

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.
$304 nightly
The price is $350
Dec 7 - Dec 8
Total with taxes and fees
East Main Lofts - Boho 203

#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.
$369 nightly
The price is $434
Dec 7 - Dec 8
Total with taxes and fees
#207 King Suites, River Views, Deck, Downtown

#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.
$369 nightly
The price is $434
Dec 7 - Dec 8
Total with taxes and fees
#209 Kings, River View, Deck, Bicentennial Park

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.
$407 nightly
The price is $468
Dec 7 - Dec 8
Total with taxes and fees
The Hanover Haven - Slice of Paradise - 10 minutes to Downtown Madison

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

2.0 star property
Madison
$608 nightly
The price is $699
Dec 7 - Dec 8
Total with taxes and fees
Madison Manor By the River: Sleeps up to 15, Walk to Historic Downtown

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.
$852 nightly
The price is $980
Dec 8 - Dec 9
Total with taxes and fees
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

Find out more about Jefferson County

Discover your perfect Jefferson County vacation rental with Expedia

How many vacation rentals are available in Jefferson County?


Expedia has plenty of vacation rentals to choose from in and around  Jefferson County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Jefferson County?


The selection of Jefferson County vacation rentals we have selected for you start as low as $168 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Jefferson County?


Vacation rentals in Jefferson County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Jefferson County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Jefferson County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Jefferson County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Jefferson County?


Find vacation rentals in Jefferson County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Jefferson County.  


What amenities are available in a vacation rental in Jefferson County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Jefferson County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Jefferson County?   


Everytime is a great time to head to Jefferson County! Staying in a Jefferson County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Jefferson County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Jefferson County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Jefferson County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Jefferson County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.