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Laid Back Getaway at Summer's Place

Currently decorated for Christmas and ready for you to experience the holidays here in historical Madison. The cottage is located just steps away from the beautiful Heritage Trail and one block from Main Street; nestled at the end of a quiet street with minimal traffic -four blocks to the river. Madison offers many festivals & community events. You'll be close enough to walk and far enough to enjoy your peace & quiet. Restaurants, stores and great coffee shops are all in walking distance.

T&E Riverhouse Retreat

Experience the perfect blend of relaxation and recreation at our stunning property with panoramic river views. Enjoy direct beach access, where you can soak up the sun, swim, fish, kayak, and more. The home features upper/lower decks, a basketball goal, fire pit, and a kitchen on each level. Whether you're here for a peaceful getaway or an action-packed vacation, this riverfront retreat has everything you need for an unforgettable experience. Book your stay today and create lasting memories.

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.

3-suite cottage spa (aaaah!) house

Treat yourself to a feel-good gathering place for up to six. Our well-stocked kitchen will support your meals together, with concierge food services upon request, cappuccinos by Breville Barista Touch and more nice extras. Linen sheets, feather pillows and comforts abound. Rest well and take time for a soak in the air jet tub or an oversized stone tub. (Be sure to try the Toto Washlet, too!) — Madison has so much to offer, but you may simply want to bask in pampered retreat at Stay Lello.

The Hanover Haven - Slice of Paradise

Escape to this peaceful farmstead just outside of town for a truly relaxing getaway. The back porch is great for watching stunning sunsets over the pond and overlooking the active horse pasture! Stocked with top-quality fishery, it's a paradise for fishing enthusiasts. Nestled right up the road from Hanover College, 10 minutes from Historic Downtown Madison and Clifty State Park, and just 3 minutes from a local store. Book your stay now and enjoy the tranquility of this unique retreat!

Fiona’s Boho Retreat

Did you ever wish you could decorate for your own personal pleasure? Our kids are grown so that’s what we’ve done! If you are searching for Pottery Barn decor you will be disappointed BUT if your adventurous side likes eclectic,boho meets MCM space that’s not perfect but perfectly lived in, this is for you. Walkable to downtown, 3.5 blocks to the beginning of the tourist area and 4 blocks from the river. On a quiet street,great neighbors and pet friendly. We hope you enjoy!

Modern Nature Cabin | Private Escape in the Forest

Escape to this charming 1BR/1BA retreat at Pole Barn, where rustic character blends with cozy, modern amenities. Nestled in a peaceful setting, it’s ideal for a relaxing getaway, creative retreat, or quiet work-from-home escape. The space features a comfortable bedroom, spotless bathroom, convenient kitchenette, and tranquil views of nature. Just minutes from Hanover College and historic downtown Madison, IN — perfect for exploring local shops, dining, and scenic riverfront walks!

Romantic Retreat w/ Hot Tub-5 min from downtown

Soak in your private hot tub under the stars while the firepit glows beside you — the perfect romantic escape just 5 minutes from Madison’s historic riverfront. This cozy cottage combines luxury touches (Sleep Number bed, massage chair, spa-style extras) with unforgettable experiences: stargazer projector, outdoor movie nights, and complimentary first bundle of firewood. Upgrade your stay with our romance, outdoor movie or fall picnic experience! Pls note: must be 25 to rent.

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.

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.

Stoney Creek Cabin - Sit back and unwind

Welcome to Stoney Creek Cabin. This charming 2 bedroom cabin is nestled in the hills of Madison, IN. Situated far enough away to offer all the privacy you want, yet only 8 miles from historic downtown, where there are so many gems nearby to explore. Enjoy the HOT TUB, wrap around porch, and patio! There could not be a more relaxing place to unwind.

Cabin in the Holler

Keep it simple at this peaceful and centrally-located cabin. Disconnect from hectic life and enjoy this slice of nature. Beautiful scenery, with a creek. We are centrally located and close to Belterra casino, Versailles park, Clifty falls, and the quaint town of historical Madison.