Vacation rentals in Jefferson County

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Top-rated vacation rentals in Jefferson County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Apartment in Madison

5.0 out of 5 average rating, 113 reviews

River's Edge II-Historic Hunger House-Downstairs

Newly renovated DOWNSTAIRS unit of this historic home in the heart of downtown Madison. Experience the unique blend of historic character and contemporary comfort! Relax on our front porch (complete with swing and river view) after a busy day of touring shops, historic sites, cultural, or music festivals that are the heart of Madison... WELCOME to the River's Edge II! Extended stay (wk-mo) discounts 21%-49% Rent one or both floors (See "River's Edge-UPSTAIRS-listing) SEND INQUIRY FOR PRICING.

Jan 15 – 22

€ 104 per night
Guest favorite

Tiny home in Madison

4.93 out of 5 average rating, 135 reviews

TINY TOO

A Tiny house located in historic Madison, Indiana. Tiny Too is located in the heart of the history of this beautiful river town. Located just steps from the Ohio River, Heritage Trail, quaint shops, local restaurants, wineries and a host of festivals. Step outside the upper and lower decks to river views. Our property is newly remodeled and equipped with all of the amenities of home PLUS outdoor seating (upper/lower decks), gas grill and bicycles. It also offers private, off street parking.

Nov 6 – 13

€ 111 per night
Guest favorite

Apartment in Madison

5.0 out of 5 average rating, 269 reviews

Stablemaster’s Quarters/ Best downtown location!

The historic building was originally one of the city’s main livery stables circa 1886. New very comfortable furnishings, a spacious gathering area, 2 large bathrooms, a laundry room and a furnished white kitchen will all be appreciated. Carefully, the historic charm is blended within. You will soon see why the entire building is award winning! This fun river town will remind you of years gone by. Come see why Ladie’s Home Journal awarded Madison “ prettiest small town in the Midwest”.

Nov 9 – 16

€ 202 per night

Popular amenities for Jefferson County vacation rentals

Other great vacation rentals in Jefferson County

Guest favorite

Home in Madison

4.94 out of 5 average rating, 32 reviews

Your Madison Home Away from Home

Jan 9 – 16

€ 150 per night
Guest favorite

Guesthouse in Madison

4.94 out of 5 average rating, 50 reviews

Studio apartment above Garage in downtown Madison

Aug 11 – 18

€ 97 per night
Guest favorite

Home in Madison

5.0 out of 5 average rating, 24 reviews

The Book Haven - A Book Lover's getaway near Main

Dec 18 – 25

€ 149 per night
Guest favorite

Tiny home in Milton

4.84 out of 5 average rating, 74 reviews

The Rustic River Retreat.

Oct 29 – Nov 5

€ 131 per night
Guest favorite

Bungalow in Madison

4.97 out of 5 average rating, 34 reviews

Spacious 2 bedroom 1.5 bath home in Downtown.

Nov 8 – 15

€ 160 per night
Guest favorite

Home in Madison

4.93 out of 5 average rating, 82 reviews

Cozy 3 bedroom home, steps away from Main Street

Jul 16 – 23

€ 162 per night
Guest favorite

Home in Milton

5.0 out of 5 average rating, 11 reviews

The Madison-Milton Cabin

Dec 18 – 25

€ 167 per night
Guest favorite

Cottage in Madison

4.94 out of 5 average rating, 49 reviews

Riverfront Cottage downtown Madison

May 7 – 14

€ 166 per night
Guest favorite

Home in Madison

4.97 out of 5 average rating, 59 reviews

Lavender House

Aug 5 – 12

€ 145 per night
Guest favorite

Home in Madison

4.93 out of 5 average rating, 74 reviews

Lanier View ll (Perfect for Social Distancing)

May 17 – 24

€ 163 per night
Guest favorite

Cabin in Madison

4.99 out of 5 average rating, 76 reviews

Wolf Creek Cabin

Jan 11 – 18

€ 207 per night
Guest favorite

Home in Madison

4.96 out of 5 average rating, 53 reviews

Riverview Historical Retreat

Jul 17 – 24

€ 177 per night

Destinations to explore