Holiday houses in Milton

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

4.98 out of 5 average rating, 243 reviews

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

4.95 out of 5 average rating, 118 reviews

Home in Versailles

School Days

Sharpen your pencils and reminisce about your childhood school days in this beautifully reconstructed schoolhouse. Built in 1879, this gorgeous property is situated just minutes from local coffee shops, locally owned restaurants, antique shops and the second largest State Park in Indiana. Be entertained with live music, museums, and other attractions by visiting three conveniently located cities. Come enjoy the modern amenities as well as the historical features this schoolhouse has to offer.

4.99 out of 5 average rating, 214 reviews

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

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

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

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.

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, 120 reviews

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.

4.89 out of 5 average rating, 218 reviews

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.

4.96 out of 5 average rating, 127 reviews

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.

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Popular amenities for Milton holiday rentals

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Other great holiday rentals in Milton

5 out of 5 average rating, 82 reviews

Walnut Street Saloon BNB

SharonRating, 5 stars1 week ago

Highly recommend this rental. The location is great! We gathered for a family get together and it was spacious and comfortable. The history of the building and neighborhood was charming too. Our host made us feel very welcome.

5 out of 5 average rating, 66 reviews

Guest suite in Hanover

OFF THE CLOCK River House

KylieRating, 5 stars8 months ago

Amazing hosts! Great place with a beautiful view! Incredibly friendly and helpful and we had the best time! Thank you!!

5 out of 5 average rating, 23 reviews

Annies Fabulous Federal house

LaurenRating, 5 stars1 week 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!!

4.95 out of 5 average rating, 21 reviews

Home in Hanover

The Hanover Haven - Slice of Paradise

GlenRating, 5 stars3 weeks ago

We had a wonderful stay at Jordan’s place! The house was incredible—spacious, spotless, and thoughtfully prepared for guests. We especially loved the beautiful view overlooking a pond and horse pastures—it was so peaceful and relaxing. The location was perfect for us, with easy access to Hanover College, which made attending graduation weekend smooth and stress-free. Jordan was a great host, and we would absolutely stay here again. Highly recommended!

4.88 out of 5 average rating, 8 reviews

Little Pink House - North

AmberRating, 5 stars1 month ago

Love this place 🤍

5 out of 5 average rating, 27 reviews

Apartment in Madison

Livery Loft: BEST location!

TerryRating, 5 stars2 weeks 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, 95 reviews

Watchmaker Place in Historic Madison District

BeckyRating, 5 stars4 days ago

I booked this place for a girls' weekend, and we all loved the house. The design, amenities, and location were great—close to Main Street and the Riverwalk. It was clean and well-stocked with everything we needed.. Christopher, the host was responsive and friendly to communicate with. I highly recommend this place to anyone looking for a wonderful space and atmosphere.