Milton Vacation Rentals

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Dec 19 - Dec 21
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In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Milton

TV, fireplace
Cozy Cabin Madison Indiana

Cabin in 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!

Cabin in 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…

Apartment in 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

Apartment in Madison

10.0 out of 10, Exceptional, (21)
"Great downtown location in a peaceful little town. "
United States
Megan M.
$161 nightly
The price is $185
Dec 7 - Dec 8
Total with taxes and fees
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!

Vacation Home in Madison

9.8 out of 10, Exceptional, (51)
"It is a nice place. We were able to walk to the river and main street fairly easy. "
United States
Paul W.
$216 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Exterior
Cozy Tiny House in Scottsburg

Vacation Home in Scottsburg

9.4 out of 10, Exceptional, (3)
"Cute, clean, and comfortable stay! Great communication with host! "
United States
Teresa B.
$154 nightly
The price is $172
Dec 29 - Dec 30
Total with taxes and fees
Cozy Tiny House in Scottsburg
Exterior detail
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!

Vacation Home in Hanover

9.8 out of 10, Exceptional, (33)
"Great place to stay for Hanover college "
United States
Lindsey M.
$218 nightly
The price is $251
Dec 7 - Dec 8
Total with taxes and fees
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Dining
Madison's Only YURT Experience

Vacation Home in 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

Vacation Home in 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.
$224 nightly
The price is $228
Dec 8 - Dec 9
Total with taxes and fees
Sleeps 4, Rustic, Secluded
Exterior
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV

Apartment in Madison

2.0 star property
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.
$146 nightly
The price is $168
Dec 8 - Dec 9
Total with taxes and fees
Cozy 1-bedroom apartment in fabulous Madison with WiFi, AC, Smart TV
Smart TV, fireplace, video games, DVD player
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Cabin in 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.
$423 nightly
The price is $478
Dec 8 - Dec 9
Total with taxes and fees
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths
Interior
#207 King Suites, River Views, Deck, Downtown

Vacation Home in 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.
$369 nightly
The price is $434
Dec 7 - Dec 8
Total with taxes and fees
#207 King Suites, River Views, Deck, Downtown
Dining
Enchanting, energizing, and enjoyable!

Vacation Home in 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
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

Apartment in Madison

9.8 out of 10, Exceptional, (10)
"Super comfortable, clean little apartment in a quiet area off the main strip. We loved out stay!"
United States
Courtney G.
$126 nightly
The price is $129
Jan 4 - Jan 5, 2026
Total with taxes and fees
Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Property grounds
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Cabin in 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

Vacation Home in Madison

2.0 star property
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

Vacation Home in Madison

10.0 out of 10, Exceptional, (25)
"Wonderful place to stay "
United States
Susan H.
$212 nightly
The price is $244
Dec 18 - Dec 19
Total with taxes and fees
The Artist’s A-Frame
Exterior
Charming 3-bedroom house in lovely downtown Madison.

Vacation Home in Madison

2.0 star property
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.
Interior
Stoney Creek - Sit back and unwind

Cabin in 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
Fridge, microwave, oven, stovetop
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

Vacation Home in 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 4 days ago
Hillside Inn

Find out more about Milton

Everything you need to know about Milton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Milton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Milton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Milton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Milton. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Milton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Milton rentals

At Expedia, we put the best Milton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Milton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Milton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Milton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.