Vacation rentals with a fireplace in Jefferson County

The Raven

Experience the poetic intersection of art and mortality at The Raven. This stay is a tribute to Edgar Allan Poe & the "beauty in death," where the macabre is met with elegance and the transient nature of life is celebrated through high-Gothic design. Surround yourself with a collection of decor from intricate skull art to watchful ravens within a space that transforms "darkness" into a moody retreat. Indulge in a stay that is as timeless as a memory and as hauntingly beautiful as a lost love.

The Row House

Modern flair with antique charm sets this BnB apart! Located on quiet street in the heart of historic downtown Madison, this fully renovated 1830s Row House has you steps away from everything! Whether it's a festival or fall colors, a boat race or car show on the riverfront, a micro brewery or winery, antiquing or historic tour, hiking Clifty Falls or simply just getting away, we have the location for you. *HVAC system includes whole-house air purifier. Max of 4 guests, no children under age 8.

Cedar Rustic Cabin at Lost Trails

Nestled among four other cabins thoughtfully placed across 45 wooded acres, the Cedar Rustic Cabin offers a peaceful retreat designed for couples or solo travelers. Enjoy walking trails, tranquil ponds, and wildlife sightings minutes from historic downtown Madison. This cozy one-bedroom cabin features a full kitchen with cookware, Keurig and standard coffee makers, toaster, washer and dryer, a living area with double recliner, and a wraparound deck perfect for relaxing and enjoying wooded views.

Livery Loft: BEST location!

This beautiful loft apt is spacious and guests say "it's beyond amazing"! 2+ bdrm 2 luxury bathrooms offer SO many amenities you won't want to leave! It has a very spacious living room, dining room & gourmet kitchen. The master bath has a fireplace above the soaking tub & a massage shower. The other bath has a rainfall shower and heated toilet seat: add luxury linens & you will feel very pampered! We have the best location just off main street and 3 blocks from the relaxing riverwalk.

Family-friendly cabin with game room and backyard!

Gather with your group in this inviting retreat featuring generous living space and modern comforts. Relax by the cozy indoor fireplace, prepare meals in a full kitchen with a center island cooktop, or unwind in the private backyard. With three comfortable bedrooms—including a primary suite with balcony—plus a game room with bunk beds, this home easily accommodates up to ten guests. Convenient parking and smart amenities throughout make this house the perfect blend of comfort and convenience.

The Madison-Milton Cabin

Welcome to the Madison Milton Cabin. Enjoy a unique, peaceful setting just 5 minutes from Downtown Madison. Enjoy the great shopping, dining, and entertainment and finish your day relaxing next to a cozy outdoor fire. If you love sunsets you will love the views from the cabin. The house features a loft bedroom with comfy adjustable bed. The bathroom includes an oversized soaking Tub/Shower and the main living room includes a queen size pull out couch. Stay connected with high speed internet.

Annies river house!

Your group will enjoy Annies River House! Located on Main Street in beautiful historic Madison. We are just blocks from the majestic Ohio river, shopping, eateries and wineries! Rent a golf cart and maneuver through town with ease! Take in the history, the beauty and architecture of times past and know you have a comfortable spacious place to retire at the end of the day at Annies River House! Additional $10.00 per guest over two. One time fee. Additional $75.00 pet fee. One time fee.

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.

Cabin on the Ridge

Welcome to Cabin on the Ridge, your tranquil retreat nestled in the scenic hills of Madison, Indiana. Just 25 minutes from downtown Madison, our cabin offers a perfect blend of rustic charm and modern comfort. Madison, awarded the “Best Small Town in the Midwest” by USA Today and the Great American Main Street Award, is a must-visit. Enjoy the historic architecture, boutique shops, and delightful eats, or explore Clifty Falls State Park. •Fast wifi •Roku TV/Streaming services •Keurig

Hardy Lake Vacation House

The House sits On Hardy Lake. 2 beds, 2 bath. Inside it has a full kitchen . The living room has queen sized sofa beds for extra guests. Gas grill and wood burning Fire pit, hot tub. Self-check-in. Smart TV that gets local channels. We provide board games, playing cards. Quiet getaway where guests can simply relax away from the city. 15 minutes from Scottsburg IN, 50 minutes from Louisville Ky. Lakeside Camping 4 min, Hardy Lake public Beach 15 min. Boat parking space available

Rivertown Retreat in Historic Downtown

Located in beautiful, historic downtown Madison! Lisa and Richard co-own and co-host this adorable, recently updated Rivertown Retreat from the 1850s. It is one block from Main Street, featuring so many charming shops, restaurants, and historic buildings Madison is famous for. Three blocks from the mighty Ohio. A short five-minute drive from Clifty Falls State Park. We fell in love with Madison and know you will, too.

Historic 1830s Log Cabin in Madison, IN

Beautiful historic 1830s log cabin nestled in the woods of Dugan Hollow! A 2-story cabin with 2 authentic lofted bedrooms, an indoor jacuzzi tub, fireplace and baby grand piano. Uniquely situated only 5 minutes from Historic Madison, Indiana on the Ohio River; 15 minutes from Clifty Falls State Park; and 20 minutes from Big Oaks National Wildlife Refuge. *Small dogs allowed with prior approval, see below.*