Vacation Rentals By Owner In Madison, IN

Come enjoy the best of both worlds in our beautiful historic town! Cypress Grove Inn is approximately 1 mile from our beautiful downtown area. Cypress Grove Inn gives you the peace of the country along with the sounds of nature. A short drive and you will enjoy Madison Main St., where numerous restaurants and retailers await you!brYour accommodations are approximately 1800-2000 square feet, the accommodations are half of the house, large outer deck with 2 fire pits, hot tub, and fishing if you choose.brIt provides privacy at its best!brConsisting of 2 bedrooms,each with Queen bed, one full bathroom, and separate area with a small fridge, coffeemaker, and snacks.brLiving room with dining table, smart tv, electric fireplace, indoor fountain. brCleaning fee-$75brbrOur accommodations provide spacious rooms, closets, and individual patio seating over looking a Spring fed pond fully stocked with fish-- bring your poles, and enjoy a rest in the hot tub! brOur sunrises and sunsets are amazing, and the views will take your breath away. You most likely will encounter deer, wild turkey, and many other sights. Bring your bikes, hiking gear, and take a peaceful walk around the property or at Clifty Falls State Park that is only 6 miles away, local wineries with beautiful landscapes, walk the beautiful river-walk, and enjoy some of Madison's Magical Musicians in our historic taverns or outdoor venues.brbrYour host and hostess Tom and Chandra Ferry will greet you upon your arrival!brCode locks are used and codes will be given prior to arrival. brFeel free to pull up to the main front door to unload your belongings. There is additional parking available on the west end of the driveway.brUnfortunately, at this time we are not handicap accessible, however access into home is one level. There are stairs to the rooms. brbrThe Cypress Grove Inn is truly unique as it was built in 1825.brA true historical home, exhibiting the original hardwood floors, muscat shots embedded in the original exterior and interior field stone, five acres of property for you to take walks, a full spring fed pond that is open for fishing , quick access to Madison downtown/ various landmarks., and patio areas to embrace the beautiful sunrise and sunsets.brbrThere is so much to enjoy here in Madison, IN.brCome enjoy the best of both worlds-- Cypress Grove Inn looks forward to accommodating you!brbrGetting around--brGolf cart rentals available downtown-Acree Alley Carts. brInquire with hosts- we are happy to set a reservation for you! brCab service available as well.brList of suggested places to visit is provided. brbr**Hot Tub is located on lower deck area. There are safety guidelines listed once checked in. brbr**Checkout procedure- please just text hosts once you have departed. (317-625-8311). brAll towels, sheets, trash hosts will take care of for you. brIf there is an excess of trash feel free to place in dumpster and the north end of the house ( front). brIf any damage had occurred please Inform hosts prior to departing. brbrThank you for staying with us!

The Cypress Grove Inn ~Madison, IN!
*5 Star hosts!

Madison, Indiana, United States

Bed

Bath

Sleeps

$228.08

Drive across the creek and escape to the woods in this spacious, rustic cabin on the creek. Giant living room, plenty of cozy seating and attached dining room. Bring the whole family or have a romantic getaway. 15 min from historic Madison.

Rustic cabin just outside of Madison!

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(52)

$234.6

You will be close to everything when you stay at this centrally-located home. This historical landmark was built by and located next to The Francis Costigan Historical Home. You will be steps away from the Broadway Fountain, downtown shopping, and only a few blocks from the majestic Ohio River. This three bed, 1/12 bath home boats tall ceilings and large rooms which makes it a great place to stay with family or friends.

Beautiful and spacious 3BR historic home centrally located in downtown, Madison.

Madison, Indiana, United States

Bed

Bath

Sleeps

$191.71

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.

Stoney Creek - Sit back and unwind

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(66)

$185.27

Beautiful Ohio River Frontage views from EVERY room (even the bathroom if the door was open!). Newly remodeled. Rural setting but close to town-5 minutes. Quiet nights. Swing on the country porch watching river roll by. Super clean and cleanable historic home. Carport, Woods. Waterfront theme. Watch fireworks from the porch or master bedroom. Handmade local amenities-natural soaps & spa products by award winning Fountain Alley BodyCare in MadisonbrbrThe spacebrOn designated Scenic Highway. This home was once an early trading post with a ferry that would cross the Ohio River. It had gambling and was used back then for hourly or overnight stays. It sets outside city limits and besides the busy highway during the daytime hours, it’s quiet and peaceful. Boats welcome.brJust outside of historic Madison Indiana, a stellar community, on historic registry, and just a beautiful place to go with shopping and restaurants and a state park! brbrGuest accessbrWhole house (excluding laundry room), large west side yard, short wooded trail behind home. The highway gets busy, be careful! brbrOther things to notebrThe highway is close and busy in the day. Pulling in and out of the driveway should be exercised with extreme caution. Children and elderly, pets, should be watched to stay away from the busy highway.brANOTHER CAUTION: tall people be aware that the down stairs bathroom has a low clearance doorway, the stairway is low clearance, and a few beams throughout the home are low clearance. brbrThe sleeping arrangements are: there is one completely private room with a twin and full sized bed. The master bedroom- with king bed- one must go through to get to the private room with the 2 beds. There is a hide a bed couch in the great room. The master bedroom is the nicest room but again it is open to the guest bedroom so not super private but roomy and the best view with sliding doors. This master bedroom has no door but is upstairs. See photos

River Views from Every Room! Clean Fun, Secluded, but close to town. Pool table

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(10)

$282.55

Newly remodeled, well furnished, spacious one story home in the heart of everything going on in historic downtown Madison, Indiana.brbrSteps from the river puts you on the doorstep of the Riverwalk and all the festivals on Vaughn Dr.brbrJust 2 blocks to Main St makes an easy walk to all of the shopping, dining and events on Main St.brbrClose to the public boat ramp and ample room for boat parking make this a boaters dream.brbrShort drive to Clifty Falls State Park and Hanover CollegebrbrViews of the Ohio River and Madison bridge are beautiful from the front porch.brbrThis home is completely contactless. You will receive a door code the day before your stay for a contactless entry.brbrThis home is a duplex. Inside the front door is a foyer area which contains the front door to the home. Riverside Retreat 2 is the right side of the duplex featuring 3 bedrooms, 2 full baths, spacious living room, workspace, laundry room, full size dining room and large well stocked kitchen.brbrLinens and towels are included along with a limited supply of other essentials such as coffee, body wash, shampoo, conditioner, hand soap, toilet paper, dish soap and paper towels.brbrConsider renting the entire duplex to have a 6 bedroom/4 bathroom home under one roof. Check out Riverside Retreat at brhttps://www.vrbo.com/4277632 dateless=true

Riverside Retreat 2 ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

Madison, Indiana, United States

Bed

Bath

Sleeps

$129.49

Discover the charm of Madison from our Est 1925 Historic Overlook Suite 107. Nestled in a prime location, this cozy 1-bedroom, 1-bathroom rental offers a perfect blend of comfort and convenience. Enjoy modern amenities such as a fully equipped kitchen, and laundry facilities to make your stay as comfortable as possible. Immerse yourself in the rich history and vibrant culture of Madison with this delightful retreat as your base. We are conveniently located close to all of the local attractions.

The Madison Inn, Est 1925 Historic suite 107

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(7)

$161.45

pDiscover the charm of Madison from the comfort of Historic Woodside view Suite 205. This cozy 1-bedroom, 1-bathroom rental is your perfect getaway, offering essential amenities to ensure a seamless stay. Enjoy the convenience of being close to all the local attractions. Unleash your culinary skills with our full kitchen or enjoy one of our local establishments. Nestled in a prime location, this suite promises a memorable stay for those seeking both relaxation and adventure./p

The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(11)

$121.0

Welcome to Hometown on Main, Suite 102, nestled in the heart of Madison. This cozy 1-bedroom, 1-bathroom rental is your perfect getaway, offering a blend of comfort and convenience. This room overlooks downtown Madison and is convenient to all the historic sites and local dining. Enjoy your morning coffee while overlooking downtown Main Street. Immerse yourself in the charm of Madison while enjoying the comforts of home. Ideal travelers or couples seeking a serene retreat.

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(10)

$186.21

pDiscover the charm of Madison from our Historic City Overlook Suite 206. Nestled in a prime location, this cozy 1-bedroom, 1-bathroom rental offers a perfect blend of comfort and convenience. Enjoy modern amenities such as a fully equipped kitchen, and laundry facilities to make your stay as comfortable as possible. Immerse yourself in the rich history and vibrant culture of Madison with this delightful retreat as your base. We are conveniently located close to all of the local attractions./p

The Madison Inn, Historic city overlook suite 206, Historic city overlook suite 306

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(3)

$53.43

Discover the charm of Madison in our cozy Southern View on Main Suite 202. Nestled in a prime location, this 1-bedroom, 1-bathroom rental offers a perfect blend of comfort and convenience. Enjoy essential amenities like a fully equipped kitchen, and full laundry to make your stay as comfortable as possible. Whether you're in town for business or leisure, our suite is the ideal home away from home conveniently located to all the downtown attractions.

The Madison Inn, Southern view on Main suite 202, Southern view on Main suite 202

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(18)

$131.6

pDiscover the charm of Madison from our cozy suite, Sunset over the City Suite 201. Perfect for couples or solo travelers, this 1-bedroom, 1-bathroom rental offers a beautiful view of Historic downtown Madison. Enjoy modern conveniences like a full kitchen for your culinary adventures, laundry facilities, and all the essentials. Located in the heart of Madison, you're perfectly positioned to explore the city's delights. Don't miss the breathtaking sunsets./p

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(12)

$145.5

Experience beautiful Mornings in this Corner suite. Rest with a beautiful view of Downtown or enjoy a peaceful stroll down Main Street. This suite is located right on Main Street and is a great place for resting and relaxation. If you're looking for a local dining special. Then this room is conveniently located just a few blocks from entertainment and fine dining. This cozy suite is in the heart of Historic Madison.

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(28)

$431.25

Welcome to the Jefferson Off Main home. We are pleased to offer a spacious, historic home in the heart of downtown Madison. This 1900 historic house offers 4 bedrooms and is perfect for families, or groups. The Jefferson Off Main has 3 full bathrooms and 3 king size beds for your comfort. The 4th bedroom offers a double size bed as well. Full Cental air to keep you cool in the summer and 3 electric fireplaces to keep you warm during the colder months. But the best part about the house is how close we are to Main St. You won't have to drive to get to shopping and dining.

Jefferson Off Main: *4 Beds*King Beds*Walk to Main* 3 Full Bath

Madison, Indiana, United States

Bed

Bath

Sleeps

$243.23

The Wadsworth House was built in the mid-1800s. It is a fully renovated and modern Shotgun house in a quiet part of town on the east side, walkable to all events, to the river, and to shops/boutiques on Main St. Some folks living around have been living in the area all their lives. The Wadsworth House is situated on a charming tree-lined street with lots of character. Besides being a family name, it is also named The Wadsworth House in honor of Henry Wadsworth Longfellow, whose poems I was forced to recite in the 5th grade! Hated it then, appreciate it now :)brbrOne of the original owners, a carpenter, moved into the house in 1907 and added the side hall onto the east side of this shotgun house, giving it the privacy needed for the family. He had immigrated from Germany and took a job working at the button factory in town. Hardwood floors, a modernized full kitchen with granite countertops, and king-sized beds with full tiled bathrooms make this house a comforting getaway.

The Wadsworth in National Historic District of Madison, Indiana.

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(17)

$356

Welcome to this charming house in historic Madison Indiana. This amazing property features 3 bedrooms with 2 king beds and 1 queen bed, perfect for a group of guests looking for a tremendous stay. The 2 bathrooms are equipped with all the essentials you need, including a hair dryer and a shower. Kickback, relax, and enjoy everything Madison and our 1864 historic house has to offer.

Charming 3-bedroom house in lovely downtown Madison.

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(19)

$300

Summary:brbrThis is the perfect destination for those who want to getaway yet enjoy the luxuries of nearby amenities such as Belterra Casino Resort (20 minutes), Kentucky Speedway (30 minutes) and Historic Downtown Madison (25 minutes), recognized as “The prettiest small town in the Midwest” by Ladies Home Journal and “Best Preserved Town in the Midwest” by the Chicago Tribune. brbrbrbr•Fast wifibrbr•Roku TV/Streaming servicesbrbr•Keurig (K-Cups Available)brbrbrbrThe Space:brbrYou’ll be greeted by an impressive great room that encompasses both the family room and fully equipped kitchen. Soaring vaulted ceilings and tall windows flood the space with natural light, with views of wooded seclusion. brbrbrbrTake time to relax and enjoy the full-length scenic covered-porch, with a cup of coffee or glass of wine. For nights when a chill is in the air curl up next to the electric fireplace for a movie or nightcap. This space boast both charm and comfort; enjoy your stay at Cabin on the Ridge.brbrbrbr4 Guests | 2 Queen Beds | 2 BathroomsbrbrbrbrGuest Access:brbrGuests have access to the family room, kitchen, primary bedroom, primary bathroom, guest bedroom, guest bathroom and loft. Guests do not have access to garage.brbrbrbrOther Things to Note:brbrYou may encounter wildlife on the property including deer, squirrels, turkey and more!brbrbrbrInteraction with Guests:brbrI am available to offer assistance through platform messaging, or direct booking email.

Cabin on the Ridge

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(19)

$252

Summary:brbrWelcome to the area's first new construction short term rental tailored for you, the guest. This contemporary cabin is nestled in the woods right in the heart of Amish country. brbrbrbrThis is the perfect destination for those who want to getaway yet enjoy the unique beauty of Historic Downtown Madison (25 minutes) recognized as The prettiest small town in the Midwest or chase waterfalls at Clifty Falls State Park (25 minutes).brbrbrbr•Fast wifibrbr•Roku TVbrbr•Keurig (K-Cups Available)brbrbrbrThe Space:brbrMeticulously designed with you in mind. You’ll be greeted by an impressive great room that boasts an open floor plan with brbrsoaring vaulted ceilings and tall windows that flood the space with natural light.brbrbrbrThe cozy, modern kitchen is fully equipped to meet all your needs, with all the comforts of home. brbrbrbrTake time to relax and enjoy the spacious balcony from the bedroom with a cup of coffee or glass of wine, while gazing at the stars or sunset.brbrbrbrFor nights when a chill is in the air curl up next to the electric fireplace for a movie or nightcap. This space boasts both charm and comfort; enjoy your stay at Cabin on the Ridge: The Sequel.brbrbrbr2 Guests | 1 Queen Bed | 1 BathroombrbrbrbrThe Neighborhood:brbrThe cabin is located in a remote area, surrounded by an Amish Community. The only noise you may encounter is the occasional trot of a horse and buggy down the gravel road.brbrbrbrGetting Around:brbrThe cabin is located on a gravel road, please drive slowly. I supply directions to Madison in my guidebook at the cabin. Please do not use GPS to get to Madison, as it may not take you the most direct route.brbrbrbrInteraction with Guests:brbrI am available to offer assistance through platform messaging, or direct booking email.

Cabin on the Ridge: The Sequel

Madison, Indiana, United States

Bed

Bath

Sleeps

Exceptional(33)

$180.76