Vacation rentals in Milton

A stone fireplace with a glass front is centrally located within a cozy living area, complemented by modern lighting fixtures. A small table with a decorative plant and items sits in front of the fireplace, enhancing the room's inviting ambiance.

4.99 out of 5 average rating, 528 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

4.98 out of 5 average rating, 244 reviews

The exterior of a historic brick house is displayed, featuring large windows and decorative white trim. A welcoming covered porch is present at the entrance, with a solid path leading to the door. The classic architectural details highlight its historical character.

Apartment in Madison

Rivers Edge-Historic Hunger House-Upstairs-Madison

A unique blend of historic character and contemporary comfort! Floor to ceiling windows, amazing staircase and hardwood flooring with modern kitchen & bathroom, this UPSTAIRS unit with private entrance will be your oasis. The balcony, w/view of the Ohio river, is perfect for early morning coffee or relaxing after a busy day of touring Madison. WELCOME to the River's Edge! Extended stay (week-mo) discounts 21%-49%. Rent one or both floors (See "River's Edge II-listing) SEND INQUIRY FOR PRICING

4.99 out of 5 average rating, 215 reviews

A staircase with plush green carpeting descends into a cozy living area. Large windows allow natural light to flood the space, offering an inviting view of the outdoor deck surrounded by greenery. A small table on the deck is partially visible.

Home in Bedford

Atoka Farms

If you are looking to get away in seclusion and be with Mother Nature, this is the home. Very quiet, with a running creek beside the home. Walking distance to the Ohio river, two outdoor decks, one with a grill. A car port, full kitchen, two full baths, paved driveway, trees all around. The home sits between two hill ridges surrounded by 160 acres. It is a park like setting. 30 minutes from Gene Snyder and I-71 (Louisville). Historic Lagrange Ky and Madison In, are a must see and close by.

4.99 out of 5 average rating, 226 reviews

The entrance features a red brick façade with a black front door and decorative glass panels. Two steps lead to the door, flanked by potted plants. The porch area is complemented by a wall-mounted light fixture and a welcoming atmosphere.

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.

4.98 out of 5 average rating, 108 reviews

Two wooden rocking chairs are positioned on a wooden deck, facing a large window that overlooks a natural setting filled with autumn foliage. A grill is seen nearby, and fallen leaves cover the ground, adding to the tranquil outdoor environment.

Cabin in Vevay

The Cabin

As you walk in, The Cabin wraps it's arms around you and says " Welcome home." You can feel the stress leave you as you settle in for your stay at this scenic cabin on 9.8 wooded acres. Fully furnished, spacious 1 room cabin with stone wood burning fireplace, equipped kitchen, bath with shower and twin over queen bunk bed. Refresh your mind & soul on the covered back porch overlooking the mature woods. Enjoy watching the abundant wildlife, including turkeys, deer, chipmunks and squirrels.

4.86 out of 5 average rating, 333 reviews

A private deck is presented with wooden railing, featuring a blue umbrella and several black folding chairs. A textured area rug covers part of the deck, creating a comfortable outdoor space with a view of surrounding buildings and the sky.

Loft in Madison

Historic Madison Spa Retreat perfect location

Highlighted on Madison Loft Tours. 1800s historic 3rd story charming Loft offers a spa retreat & private deck. In the midst of Madison’s shopping, dining, festivals & nightlife. Located between Main St and the river. Antique furnishings and beautiful woodwork highlighted. Sip local coffee from our private deck or relax in a jacuzzi tub after touring the sights. Wineries, bars, Mad Paddle Brewery and great restaurants surround us. Hanover College & Clifty Park are minutes away.

A landscaped backyard features a wooden pergola and various seating options. Lush greenery surrounds the area, offering a view of the Ohio River in the distance. A patio area is visible, creating a relaxed outdoor space for enjoyment.

4.98 out of 5 average rating, 142 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

An open wooden gate reveals a serene outdoor space, featuring stone pathways and lush greenery. Potted shrubs flank the entrance, while patio furniture is positioned in the distance. A clear blue sky and soft clouds offer a bright backdrop to the inviting garden setting.

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, 120 reviews

A serene view of lush green trees stretches out, showcasing the natural landscape and rolling hills. The image captures the vibrant foliage under a partially cloudy sky, creating a peaceful atmosphere within the secluded setting.

Apartment in Madison

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

Two pendant lights hang from a wooden, vaulted ceiling, casting a warm glow over the kitchen area. A stainless steel refrigerator stands adjacent to a window dressed with a light blue curtain, above which is a charming display of autumn-themed artwork.

Cottage in Madison

4.9 out of 5 average rating, 182 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.

4.96 out of 5 average rating, 128 reviews

A view through the geometric windows of the Geodome reveals a cozy interior featuring a wooden dining table and chairs. Natural light illuminates the space, highlighting the kitchen area with modern appliances. Decorative elements and a staircase can be seen, emphasizing the open design.

Dome in Vevay

Hilltop Dome, 42 secluded acres in nature

Our Geodome is tucked away on 42 private acres exclusively for you and your guest Enjoy the stars at night, fire pit, hot tub, high speed internet, washer dryer, heat and air-conditioning and all the amenities. We are conveniently located within 15 miles of Madison, IN, Vevay, IN, Clifty Falls, Belterra Casino, also within 62 miles of Cincinnati and Louisville.

A compact bathroom features a glass-enclosed shower, a small white vanity with a sink, and a toilet. Light-colored wood paneling adorns the ceiling, and white shiplap walls add brightness. A small rug is positioned in front of the vanity, with a modern light fixture above.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Milton vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Milton

A serene creek meanders through a wooded landscape, surrounded by trees displaying vibrant autumn leaves in shades of orange and green. Smooth stones create gentle ripples in the water, reflecting the blue sky and scattered clouds above.

4.99 out of 5 average rating, 83 reviews

Cabin in the Holler

BruceRating, 5 stars3 days ago

The getaway in the 'holler' felt a bit tricky to find because it is quite a ways out in the countryside but that also made it super peaceful and relaxing. Great chairs on the deck to use and comfy indoor seating. Pauline's lodging is decorated with family and local items and feels immediately comfy. The linens were great, the beds very comfortable. We were sad we were only able to stay there one night!

Superhost

Townhouse in Madison

4.84 out of 5 average rating, 25 reviews

"Madison Manor II” *Regatta Special* Great Patio

HollyRating, 5 stars2 months ago

What a great place :-) really enjoyed it definitely will be back

4.95 out of 5 average rating, 59 reviews

Bicentennial Park View

DouglasRating, 5 stars1 week 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

4.97 out of 5 average rating, 524 reviews

A lively outdoor event is captured, featuring a crowd of people engaged in various activities. A woman in an orange top is seen holding a cup, while colorful banners and tents are visible in the background, contributing to the vibrant atmosphere.

Apartment in Madison

Dragonfly Suite

DanielleRating, 5 stars4 days ago

Great spot for my husband and I to stay in Madison. Easy to walk to the Main Street attractions, the riverfront, and a short drive to Clifty Falls State Park. Loved the space!

5 out of 5 average rating, 23 reviews

Annies Fabulous Federal house

LaurenRating, 5 stars2 weeks ago

Beautiful place! My spouse and I stayed here with our 2 pups for 4 nights and it felt like a home away from home. Very cozy, and it was so clean when we showed up. The king bed was SO comfy, I wanted to take it with us when we left. I slept incredible. She left great instructions, and checking in was easy. When we visit back, we only hope this place will be available to book again!!

4.94 out of 5 average rating, 63 reviews

The warmly lit great room features rustic log walls and a stone fireplace, with a cozy seating area inviting relaxation. A flat-screen TV is positioned across from a coffee table draped in a patterned throw, while charming art pieces enhance the cabin's Americana decor.

Cabin in Madison

Historic 1830s Log Cabin in Madison, IN

DavidRating, 5 stars1 month ago

Wow! An amazing cabin in a beautiful setting. Rustic luxury. We can't wait to book a return visit. The cabin was beautifully decorated with a high attention to detail. The hosts were accommodating, and communicated clearly.

4.88 out of 5 average rating, 8 reviews

Little Pink House - North

AmberRating, 5 stars1 month ago

Love this place 🤍

The entryway features a winding staircase with black and white railings leading to the upper level. A chandelier hangs from the ceiling, illuminating the space. A wooden bench is placed against the wall, and a large mirror reflects the light from the adjacent window.