Milton Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Milton

TV, fireplace
Cozy Cabin Madison Indiana

Cozy Cabin Madison Indiana

Milton
10.0 out of 10, Exceptional, (19)
"The cabin was just as described online it's very quiet and was the perfect getaway "
United States
christy m.
Cozy Cabin Madison Indiana
4 bedrooms, free WiFi, bed sheets
Rustic cabin just outside of Madison!

Rustic cabin just outside of Madison!

Madison
10.0 out of 10, Exceptional, (53)
"Great day, we loved the cabin!"
United States
Mark C.
Rustic cabin just outside of Madison!
Interior
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

Madison
10.0 out of 10, Exceptional, (61)
"This was the best place I have ever stayed. The place was amazing and the hospitality exceeded expectations. I would definitely recommend staying here. "
United States
Adam K.
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…
Smart TV
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining

Madison
10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
The price is ￥16,683
￥33,159 total
includes taxes & fees
Dec 7 - Dec 8
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
Fridge, microwave, oven, stovetop
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Madison
9.8 out of 10, Exceptional, (50)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
The price is ￥19,471
￥38,693 total
includes taxes & fees
Dec 7 - Dec 8
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior
Cozy Tiny House in Scottsburg

Cozy Tiny House in Scottsburg

Scottsburg
9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
The price is ￥12,306
￥26,867 total
includes taxes & fees
Dec 29 - Dec 30
Cozy Tiny House in Scottsburg
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Hanover
9.8 out of 10, Exceptional, (33)
"Great place to stay for Hanover college "
United States
Lindsey M.
The price is ￥18,005
￥38,897 total
includes taxes & fees
Dec 7 - Dec 8
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Dining
Madison's Only YURT Experience

Madison's Only YURT Experience

Madison
9.2 out of 10, Wonderful, (11)
"One if the most relaxing vacations that I have ever had. Very private, quiet and no traffic. The bed was very comfortable the space of the entire yurt was amazing. My little dogs loved the goats, and running lease free. We were not looking forward to leaving. The host is wonderful too!! We highly recommend staying here!!"
United States
Sharon N.
Madison's Only YURT Experience
Exterior
Sleeps 4, Rustic, Secluded

Sleeps 4, Rustic, Secluded

Lexington
8.0 out of 10, Very Good, (4)
"The cabin and property were very clean and easy to find. We loved the back yard for chilling around after we got back from the event we were attending. Host was very friendly and had good communication. Will stay again if we are back in the area! "
United States
Nicole C.
The price is ￥16,966
￥34,870 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Sleeps 4, Rustic, Secluded
Interior
Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind

Madison
10.0 out of 10, Exceptional, (102)
"Close enough to be convenient to local attractions, out enough to be mostly quiet. "
United States
Garry B.
Stoney Creek - Sit back and unwind
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

2.0 star property
Madison
10.0 out of 10, Exceptional, (14)
"We could not have been happier with this cute little place. Wonderful location with easy walking access to both the riverfront and all Madison had to offer with shops and dining options. We would not hesitate to stay here again!"
United States
Gary W.
The price is ￥19,540
￥26,038 total
includes taxes & fees
Dec 8 - Dec 9
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Property grounds
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

Madison
10.0 out of 10, Exceptional, (312)
"My family and I have been staying here for years, and love it! Quiet, clean, and plenty to do nearby. "
United States
J B.
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.
Smart TV, fireplace, video games, DVD player
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Henryville
10.0 out of 10, Exceptional, (153)
"This is beautiful property and thoughtful amenities. The host is super responsive. We cannot wait to plan our next stay. "
United States
Katie A.
The price is ￥35,048
￥74,456 total
includes taxes & fees
Dec 8 - Dec 9
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Interior
#207 King Suites, River Views, Deck, Downtown

#207 King Suites, River Views, Deck, Downtown

Madison
10.0 out of 10, Exceptional, (36)
"This is a beautiful historic house. Everything was neat, clean and perfect working order. Will definitely stay there again."
United States
Rick M.
The price is ￥30,998
￥67,615 total
includes taxes & fees
Dec 7 - Dec 8
#207 King Suites, River Views, Deck, Downtown
Dining
Enchanting, energizing, and enjoyable!

Enchanting, energizing, and enjoyable!

Buckner
10.0 out of 10, Exceptional, (92)
"Everything was just as advertised and more the amenities and the house were outstanding!!!!"
United States
Alex K.
Enchanting, energizing, and enjoyable!
Property grounds
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Madison
10.0 out of 10, Exceptional, (209)
"Francine's Cabin is such a peaceful and private place to stay. We love it and have stayed there several times. "
United States
Tammy C.
1800’s restored log cabin on 26 private rolling wooded acres with sunset views
Microwave, oven, stovetop
Charming 2-bedroom house with a river view in wonderful Madison

Charming 2-bedroom house with a river view in wonderful Madison

2.0 star property
Madison
10.0 out of 10, Exceptional, (1)
"Great spot walkable to downtown Madison & the river area. Appreciated how well-stocked the kitchen, bathroom, and laundry were. And being able to bring a pet was a big plus."
United States
Chelsea C.
Charming 2-bedroom house with a river view in wonderful Madison
Exterior
The Artist’s A-Frame

The Artist’s A-Frame

Madison
10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
The price is ￥19,540
￥36,738 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Artist’s A-Frame
Exterior
Charming 3-bedroom house in lovely downtown Madison.

Charming 3-bedroom house in lovely downtown Madison.

2.0 star property
Madison
9.4 out of 10, Exceptional, (11)
"Great old home and cool neighborhood. "
United States
Randy S.
Charming 3-bedroom house in lovely downtown Madison.
Fridge, microwave, oven, stovetop
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

Madison
10.0 out of 10, Exceptional, (16)
"Perfect location for a long weekend getaway! Cute place and right on the river. Place was clean and cozy, host was great. "
United States
Toni N.
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Milton Hotel Reviews

Hillside Inn

Hillside Inn

10/10 Excellent
"We had a wonderful time in Madison. The hotel is quite charming and the history behind it is so fascinating. There are some minor updates that need to be repaired in Room 104, but overall, it's fine. Merry Christmas! "
Thomas 2-night trip
Posted 2 days ago
Hillside Inn

Find out more about Milton

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Frequently asked questions

Can I find vacation rentals in Milton?

Yes, we have vacation rentals close to the most popular local attractions in Milton, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Milton has to offer?

Cozy Tiny House in Scottsburg: Visitors like this Milton vacation home rental. It has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Milton?

Ohio River Valley and Ohio River are a couple of lovely local spots to get outside and enjoy nature. In the larger area, you’ll find Schofield House and Historic District.

What are vacation rentals like in Milton?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Milton. Vacation rentals feature amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for a family getaway.