Holiday houses in Jefferson County

4.99 out of 5 average rating, 527 reviews

The Artist’s A-Frame

Get away and enjoy the comfort and convenience of this unique, newly remodeled A-Frame home nestled in a quiet, safe, upscale neighborhood, minutes from Clifty Falls State Park (10 min. drive), Historic Downtown (5 min. drive), hilltop shopping (5 min. drive): Hanover College (15 min. drive) •Fast Wi-Fi •Electric Fireplace .Two 55” Roku TVs, Complimentary YouTube TV for local and cable stations •Keurig & Drip Coffee, K-cups, local coffee, tea, bottled water .Paved driveway parking .Gas BBQ grill

5 out of 5 average rating, 146 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.

4.99 out of 5 average rating, 226 reviews

Townhouse in Madison

Cozy downtown home with patio. Walk to everything.

Your family will be close to everything in downtown Madison when you stay at this conveniently located, updated home built in 1880. First floor open concept floor plan includes living room equipped w/electric fireplace and an eat-in kitchen w/bar stool seating for 4. Upstairs offers two bedrooms and full bath w/shower and old old-fashioned soaker tub. Enjoy nice weather on the fenced back patio. Note: This property contains stairs and is not recommended for guests with mobility issues.

4.86 out of 5 average rating, 141 reviews

Cottage in Madison

Cozy Cottage downtown *Pets*Trails*firepit*Clean

Sue’s Cottage is a quaint two bedroom cottage with a porch over looking the Heritage Trail of Madison. It is perfect for pets. It is a home to many species of birds and wildlife. Relax on the deck bird watching or stroll through the heritage trail & scenic railroad tracks surrounding the cottage, which leads to the river walk. We are walking distance to all historic Madison offers. We are less than a mile from Clifty Park. A portion of each stay is donated to local charity.

4.98 out of 5 average rating, 141 reviews

Riverview Historical Retreat

Full time Airbnb home in Historic Downtown Madison. This two bed, two bath home overlooks the Ohio River and includes a fully stocked kitchen, washer/dryer, screened in back porch, internet, keyless entry, and more Centrally located next to Bicentennial Park, enjoy one of the many restaurants, bars, parks, and local events, or enjoy a quiet weekend away with a weekly Music/Movie by the river, a local farmers market, and shops. There is something for everyone to enjoy in Madison

4.99 out of 5 average rating, 269 reviews

Guesthouse in Madison

Mulberry Cottage In The Heart Of Downtown Madison

This quaint studio cottage is located in the heart of Madison, Indiana. The entire building was fully renovated in 2020 and offers a modern luxurious stay in our beautiful historic town. This property features off-street parking, fast private WiFi, and complimentary beverages/snacks. Within walking distance of shopping, restaurants, and all downtown events. Few properties come close to the accessibility that this Madison cottage provides. We look forward to hearing from you!

4.98 out of 5 average rating, 119 reviews

The Treehouse - Hot Tub - Indoor Pool Get Away!

The Treehouse is a perfect retreat! It is secluded by the hills surrounding Madison. Complete privacy, yet 5 minutes from downtown, or hilltop. Year-round views of the beautiful hills of Kentucky. Winter views of the Ohio River and downtown. The house has stunning ceilings made from coastal cedar off an island near Vancouver, British Columbia and beautiful skylights in the studio and indoor pool area. This is an Adults only property. 2-night min.

Superhost

Cottage in Madison

4.9 out of 5 average rating, 180 reviews

Cozy Farmhouse Retreat in Historic District

Located in the Historic District in Madison! Lisa and Richard co-own and co-host this recently updated cottage. Welcome to our cozy, chic Farmhouse Retreat. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings for which Madison is famous. Only three blocks from the mighty Ohio and a short five-minute drive to Clifty Falls State Park. We fell in love with Madison and know you will, too.

Superhost

4.84 out of 5 average rating, 150 reviews

Carole's Cottage

Quaint cottage located in downtown Madison. A short walk to all shops & restaurants and beautiful riverfront. Guests have entire home including a screened in back porch to enjoy your morning coffee or just relax and read a book. Master bedroom has a king size bed and 2nd bedroom has a futon. Our kitchen is fully equipped, including stove, refrigerator, microwave and keurig coffee maker.

5 out of 5 average rating, 180 reviews

Charming shotgun in the heart of downtown Madison

This charming, stylish 2-bedroom shotgun house is located on Main Street in historic downtown Madison, IN. You'll be just steps away from locally owned shops, bars, and restaurants, and within walking distance of the Ohio River and Madison's many festivals and events. Enjoy off-street parking, modern amenities, and the perfect front-porch view.

4.93 out of 5 average rating, 187 reviews

Home in Hanover

Campus Cottage: Cozy, Convenient, Captivating

Charming ranch home on the edge of Hanover College campus. This 2 bed, 1 bath home contains hardwood flooring throughout, an eat-in dining area, open-concept living, and brand new furnishings. Explore the beauty of Hanover, just blocks from breathtaking Ohio River views, and 6 miles from Historic Downtown Madison.

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Other great holiday rentals in Jefferson County

Superhost

4.75 out of 5 average rating, 16 reviews

JPG Officer's Quarters

CrystalRating, 5 stars2 months ago

This place was great! Exactly as described! The hosts were phenomenal. Very responsive to anything we needed. Tons of space inside, shower was bigger than we expected. The hot water lasted longer than we expected and 6 of us could shower every morning without ever running out. That was lovely! We wanted something unique, yet affordable for spring break with our family of 9. And this provided just that. We even found a geo cache on site just down the road. A few things to note, if you’re bringing kids. There are broken buildings in the surrounding area which means there’s lots of broken glass. Our immediate housing was clear though. Made for interesting exploration. There’s very little natural light which is great for sleeping. Not so great if you lose power. We had intense storms come through the area and lost power for almost 24 hours, but our hosts scrambled to help as much as they could. Even offered to refund our last night. Brought flash lights, and kept checking in. GREAT HOSTS

4.97 out of 5 average rating, 61 reviews

Glenda’s Overlook

AdrianRating, 5 stars6 days ago

Everything was lovely! Thank you!

4.87 out of 5 average rating, 15 reviews

The Regatta Room (Unit 3) - Ohio River Views

JerriRating, 5 stars3 weeks ago

The area was amazing with shops, restaurants & museums. Short drive to downtown. The walks along the Ohio River were amazing! Would stay here again if coming to Madison! 😊

4.95 out of 5 average rating, 59 reviews

Bicentennial Park View

DouglasRating, 5 stars3 days ago

great place to stay. parked my car off street under a carport and never moved it. The river walk along the mighty Ohio was one block away and good shopping, restaurants and historic architecture best seen on foot was right there. house was clean and they thought of all the little details to make a comfortable stay. Well equipped kitchen. would definitely stay again. Also friendly neighbors and area

4.98 out of 5 average rating, 50 reviews

Cottage in Madison

3-suite cottage spa (aaaah!) house

LeslieRating, 5 stars5 months ago

We loved our stay, Colene was the best host! She had so many great dinner recommendations and was responsive when I had questions! My family especially enjoyed the little snacks and treats she left for us. I would definitely recommend this place to anyone wanting to visit Madison! Her home was beautiful and provided the relaxing vacation our family was looking forward to! The house was spotless and there were so many amenities, the location was great and I loved that there is off the Main Street parking too! Great place and great host!

5 out of 5 average rating, 27 reviews

Livery Loft: BEST location!

TerryRating, 5 stars1 week ago

Our stay at Ron and Suzie's Livery Loft was exceptional. Certainly one of the top rentals we have ever had. The theme and decor was perfect for a Livery Loft concept, with top quality furnishings and just an overall outstanding atmosphere. We have never had a rental with so many amenities, fine touches, and hospitable personal service. On top of that, the location was walkable to downtown shopping and restaurants. Madison has really come along as a destination! We just really can't say enough positives, and there are literally no constructive improvement comments that we could think of. Certainly an awesome experience and can't wait to stay in Ron and Suzie's place again!

4.95 out of 5 average rating, 94 reviews

Watchmaker Place in Historic Madison District

EdieRating, 5 stars3 weeks ago

Beautiful updated home in downtown Madison! Walkable to Main Street and river. Comfortable stay for two couples. One bathroom is on the first floor while both bedrooms are on the second floor. There are no window coverings on the first floor. Would definitely stay there again.