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Top Holiday Rentals in Milton

Cozy Cabin Madison Indiana

10.0 out of 10, Exceptional, (16)
"The cabin was just as described online it's very quiet and was the perfect getaway "
Cozy Cabin Madison Indiana

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

10.0 out of 10, Exceptional, (194)
"This was the second time we stayed at the cabin. Very peaceful, wonderful views, and only 25 minutes from downtown Madison. Highly recommend! "
1800’s restored log cabin on 26 private rolling wooded acres with sunset views

Relaxing Country Getaway

9.4 out of 10, Exceptional, (35)
"Wonderful stay, very private. Cozy place perfect for couples looking to unwind. Would stay again."
Relaxing Country Getaway

The Artist’s A-Frame

10.0 out of 10, Exceptional, (17)
"Stayed for the weekend to hike at Clifty Falls. Great location to the state park and downtown restaurants. Really pretty house with everything you’d need for a stay. Host was super nice to interact with as well. Thanks again! "
The price is £170
includes taxes & fees
19 Aug - 20 Aug
The Artist’s A-Frame

Stoney Creek - Sit back and unwind

10.0 out of 10, Exceptional, (91)
"Perfect setting. Beautiful cabin. "
Stoney Creek - Sit back and unwind

Hardy lake house. Ideal for relax fishing and spending quality time on lake.

2.0 star property
9.8 out of 10, Exceptional, (20)
"Home was exactly as described, very well kept and host was great! "
Hardy lake house. Ideal for relax fishing and spending quality time on lake.

The Wee House is a shotgun house that is remodeled with a view of the Ohio river

9.6 out of 10, Exceptional, (50)
"Fantastic location-Ohio River View; walkable to Madison’s downtown, river walk, and bridge."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river

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

9.8 out of 10, Exceptional, (36)
"We enjoyed the space. Had everything we needed. Great proximity to downtown shopping and entertainment. "
The price is £169
includes taxes & fees
18 Aug - 19 Aug
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!

Sunset over the city Suite 201, Sunset over the city Suite 201

9.6 out of 10, Exceptional, (8)
"Was just what i needed to stay the week after my dads passing. Safe,.comfortable and affordable "
The price is £103
includes taxes & fees
25 Aug - 26 Aug
Sunset over the city Suite 201, Sunset over the city Suite 201

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

10.0 out of 10, Exceptional, (47)
"Everything was really great...the property is beautiful...the amenities were amazing...and the owners so sweet and caring...the would answer a text message pronto...will stay again!"
Best downtown location! Stablemaster’s Quarters. Awarded winning! Come see why…

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

9.8 out of 10, Exceptional, (9)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS

The Blue Door Place

9.8 out of 10, Exceptional, (12)
"Location was close to highway, river and Casino."
The price is £123
includes taxes & fees
19 Aug - 20 Aug
The Blue Door Place

Rustic cabin just outside of Madison!

10.0 out of 10, Exceptional, (41)
"This was a very nice property. The cabin was so cozy and the property was beautiful. We all enjoyed our stay."
Rustic cabin just outside of Madison!

Madison's Only YURT Experience

9.4 out of 10, Exceptional, (8)
"This place is adorable and has so much potential. The beds were comfortable and the Yurt was cozy. "
Madison's Only YURT Experience

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

10.0 out of 10, Exceptional, (306)
"My family and I truly enjoyed our stay. We love coming here it has all the amenities that added to our comfort. Hosts were very accommodating which was really appreciated. "
Sonshine Cabin is your own private park. With wildlife or a hike to the creek.

KY log home close to The Ark Encounter on private 14 acres private seasonal pool

9.2 out of 10, Wonderful, (29)
"We enjoyed the space the cabin had to offer and had a great time."
KY log home close to The Ark Encounter on private 14 acres private seasonal pool

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

10.0 out of 10, Exceptional, (149)
"A beautiful place and just what we were looking for to get a bunch of people together for our DnD game. Host was responsive an accommodating to ensure our stay was enjoyable. Would stay again! "
The price is £291
includes taxes & fees
18 Aug - 19 Aug
Close to Louisville,Hot Tub,Fire Pit,Game Room, and 4 Bedrooms 3 Baths

Carol’s Cabin in the Woods in Historic Hoosier Hills

10.0 out of 10, Exceptional, (36)
"My small group wanted to relax in a quiet setting and Carol’s cabin was perfect. Extremely clean, well-provisioned, quiet and private with a beautiful property to stroll around. Would definitely come back!"
Carol’s Cabin in the Woods in Historic Hoosier Hills

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (52)
"Wonderful VRBO steps away from the Ohio River and historic Madison in a very quiet setting. The home is comfortable, clean and very well-equipped, and the seating at the rear of the house is a nice bonus! The owners are great people, and have anticipated every need for a short or long stay. Highly recommend this property!"
The Wadsworth in National Historic District of Madison, Indiana.

Bungalow on Main!!

9.8 out of 10, Exceptional, (16)
"Wonderful accommodations, beautifully decorated and very clean! We will be back!"
Bungalow on Main!!
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

Frequently asked questions

Can I find holiday rentals in Milton?

Yes, there are holiday rentals close to the most popular sights in Milton, or you can select a more secluded option if you're looking for a relaxing stay.

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

The Artist’s A-Frame: This holiday home rental outside of Milton offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a garden.

What’s there to see and do in Milton?

Explore the area and family-friendly sights such as Madison Railroad Station Museum, or get out into nature at a spot like Ohio River. In the wider area, you’ll find Historic District and Lanier Mansion.

What are holiday rentals like in Milton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Milton. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for small groups.