Milton Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Milton holiday rentals

A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

1. The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101

The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
Madison Historic District
9.2 out of 10, Wonderful, (15 reviews)
"Very easy check in and nice location. Very comfortable stay. "
United Kingdom
Michael S.
The price is HK$485
HK$862 total
includes taxes & fees
16 Nov - 17 Nov
The Madison Inn, Charolotte's Corner Overlook, Suite 101, Hometown on Main Street Suite 101
A wooden cabin with a porch, a ceiling fan, and a view of a forest.

2. Sassafras Woodland Cabin at Lost Trails

Sassafras Woodland Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (21 reviews)
"Perfect little weekend getaway "
United Kingdom
Carrie M.
The price is HK$667
HK$1,133 total
includes taxes & fees
16 Nov - 17 Nov
Sassafras Woodland Cabin at Lost Trails
A building with a brick facade, a black door, and a window with a small American flag.

3. 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, (53 reviews)
"Had a very nice stay"
United States
Brad P.
The price is HK$953
HK$1,737 total
includes taxes & fees
16 Nov - 17 Nov
The Main St. Oasis - Heart of Downtown Madison - Steps from Shopping & Dining
An outdoor patio with Adirondack chairs, a concrete pathway, and a forested backdrop.

4. Modern cabin very close to scenic riverfront walks

Modern cabin very close to scenic riverfront walks
Hanover
9.4 out of 10, Exceptional, (20 reviews)
"The space was very clean and had everything we needed! It was so close to everything but in its own secluded spot at the same time. We loved our stay "
United States
MaKayla Q.
The price is HK$364
HK$1,827 total
includes taxes & fees
3 Dec - 4 Dec
Modern cabin very close to scenic riverfront walks
A wooden deck with a metal handrail, surrounded by trees and a planter with flowers.

5. Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison

Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
Madison
9.4 out of 10, Exceptional, (20 reviews)
"Clean and cozy"
United States
Julie
The price is HK$699
HK$1,273 total
includes taxes & fees
16 Nov - 17 Nov
Cute Cottage/Pet Friendly/Clean/Trails/ Nature and Historic Madison
A wooden cabin with a covered porch, a ceiling fan, and a window overlooking a forest.

6. Maple Cozy Cabin at Lost Trails

Maple Cozy Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (17 reviews)
"The overall stay was perfect for just the two of us and we loved how everything was a close drive but still felt far enough away. "
United States
Shyanne D.
The price is HK$785
HK$1,277 total
includes taxes & fees
16 Nov - 17 Nov
Maple Cozy Cabin at Lost Trails
A living room with a round mirror, two chairs, a coffee table, a microwave, and a refrigerator.

7. Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison

Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
Madison Historic District
9.6 out of 10, Exceptional, (9 reviews)
"Excellent location, nice deck and spa. Comfy bed large space."
United States
Zoey S.
The price is HK$840
HK$1,381 total
includes taxes & fees
1 Dec - 2 Dec
Enchanting Historic Spa Loft. 3rd story private deck/jetted tub/Heart of Madison
A wooden deck with two black rocking chairs and a small table, surrounded by a wooden railing.

8. Walnut Secluded Cabin at Lost Trails

Walnut Secluded Cabin at Lost Trails
Madison Township
10.0 out of 10, Exceptional, (12 reviews)
"It was a beautiful property, very clean, new amenities, enjoyable, quiet"
United States
Jason H.
The price is HK$785
HK$1,277 total
includes taxes & fees
16 Nov - 17 Nov
Walnut Secluded Cabin at Lost Trails
A wooden deck with two rocking chairs and a small table, surrounded by a wooden railing and a forested background.

9. Mulberry Secluded Cabin at Lost Trails

Mulberry Secluded Cabin at Lost Trails
Madison Township
9.8 out of 10, Exceptional, (8 reviews)
"Overall great stay and will be back!"
United States
Christina J.
The price is HK$785
HK$1,295 total
includes taxes & fees
23 Nov - 24 Nov
Mulberry Secluded Cabin at Lost Trails
A wooden log cabin with a dark brown door featuring a metal latch and a glass panel.

10. Cedar Rustic Cabin at Lost Trails

Cedar Rustic Cabin at Lost Trails
Madison
10.0 out of 10, Exceptional, (32 reviews)
"Charming, cozy cabin! Perfect for a weekend getaway!"
United States
Mollie B.
The price is HK$863
HK$1,384 total
includes taxes & fees
17 Nov - 18 Nov
Cedar Rustic Cabin at Lost Trails
A two-story house with a dark blue exterior, a front porch, and a gravel driveway.

11. 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, (80 reviews)
"The place is very clean, also convenient and close to down town. Check in and everything was very smooth! I recommend this cute little place especially for young families."
United States
Kyle A.
The price is HK$847
HK$1,624 total
includes taxes & fees
16 Nov - 17 Nov
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

12. The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201

The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
Madison Historic District
9.6 out of 10, Exceptional, (23 reviews)
"Our room was so cute and perfect for a couple. We loved it! The location was perfect as well!"
United States
Stee
The price is HK$510
HK$880 total
includes taxes & fees
14 Dec - 15 Dec
The Madison Inn, Sunset over the city Suite 201, Sunset over the city Suite 201
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

13. The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102

The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
Madison Historic District
9.8 out of 10, Exceptional, (13 reviews)
"We enjoyed our visit and would recommend to others looking for a convenient location and comfortable stay."
United States
Renee M.
The price is HK$486
HK$830 total
includes taxes & fees
7 Dec - 8 Dec
The Madison Inn, Hometown on Main Street, Suite 102, Charlottes corner overlook, Suite 102
A covered porch with a wooden door, potted plants, and a metal railing.

14. The Artist’s A-Frame

The Artist’s A-Frame
Madison
10.0 out of 10, Exceptional, (42 reviews)
"Lovely! We really enjoyed this amazing house!"
United States
Roxann W.
The price is HK$1,075
HK$1,854 total
includes taxes & fees
18 Nov - 19 Nov
The Artist’s A-Frame
A covered wooden deck with rustic wooden chairs and a rope barrier.

15. Stoney Creek - Sit back and unwind

Stoney Creek - Sit back and unwind
Madison
10.0 out of 10, Exceptional, (135 reviews)
"Our family enjoyed our stay."
United States
Shanna S.
The price is HK$981
HK$1,950 total
includes taxes & fees
24 Nov - 25 Nov
Stoney Creek - Sit back and unwind
A wooden door with a glass panel and a welcome mat at the entrance.

16. 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
9.6 out of 10, Exceptional, (55 reviews)
"Great place to stay for touring in historic Madison Indiana!"
United States
Linda G.
The price is HK$1,024
HK$2,017 total
includes taxes & fees
18 Nov - 19 Nov
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
A residential property with a red door, a small front yard with grass and shrubs, and a neighboring church with a steeple.

17. Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River

Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
Madison Historic District
9.0 out of 10, Wonderful, (2 reviews)
"Good location, well stocked with essentials."
United States
Leslie W.
The price is HK$1,024
HK$1,917 total
includes taxes & fees
16 Nov - 17 Nov
Historic Hideaway - Steps to Main St, Shopping, Dining, & the Ohio River
A stone wall with a metal gate and a sign that reads "The Madison Inn Circa 1925."

18. The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205

The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205
Madison Historic District
10.0 out of 10, Exceptional, (11 reviews)
"Cozy, peaceful, wonderful with great location. "
United Kingdom
Ed E.
The price is HK$471
HK$847 total
includes taxes & fees
7 Dec - 8 Dec
The Madison Inn, Historic woodside view suite 205, Historic woodside view suite 205
An outdoor patio with wicker furniture, a fire pit, and a table with candles and fruit.

19. Romantic 1 BR Retreat on the edge of woods with private hot tub

Romantic 1 BR Retreat on the edge of woods with private hot tub
Madison
10.0 out of 10, Exceptional, (1 review)
"This was a relaxing & romantic way to celebrate our 57th wedding anniversary. Everything was clean & the host very cordial. We enjoyed the rear deck with its fireplace & hot tube as as the comfortable bed & romantic tent interior."
United States
jon h.
The price is HK$1,255
HK$1,967 total
includes taxes & fees
16 Nov - 17 Nov
Romantic 1 BR Retreat on the edge of woods with private hot tub
An outdoor patio with a hot tub, a fire pit, and string lights.

20. "Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8

"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
Madison Historic District
10.0 out of 10, Exceptional, (22 reviews)
"This was perfect for our family of 6, the house was super clean and within walking distance to the river and many restaurants and shopping. We will definitely be staying again."
United States
George S.
"Madison Manor II” | Hot Tub, Game Room, Movie Theater | 2 BR, 2½ Bath, Sleeps 8
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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Find out more about Milton

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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?

Red comfy cottage : This holiday home rental outside of Milton offers an indoor pool, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 wider area, you’ll find Schofield House and Historic District.

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.