Holiday Homes in Milton

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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Holiday Homes in Milton

River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Modern kitchen with stainless steel appliances, light grey cabinetry, and a black and white patterned rug.

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

10.0 out of 10, Exceptional, (5)
"Great location and wonderful house!"
River Living - One Story - 2 bd/2ba - On the River - 2Blks to Main St - VIEWS
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Enjoy cooking and socializing in this kitchen with a central island and bar stools, featuring stainless steel appliances and a pendant light fixture.

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

9.8 out of 10, Exceptional, (35)
"Clean, comfortable home with everything needed for our stay. "
The price is AU$390
includes taxes & fees
10 Aug - 11 Aug
Glenda’s Overlook..everything you need to make visiting Madison a great getaway!
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
Stylish home with a small front porch and sheltered entryway.

Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River

9.8 out of 10, Exceptional, (39)
"House was clean and cozy, great weekend getaway place. "
Historic Home! Walking Distance to Shops, Restaurants, Events, & Ohio River
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
Compact kitchen with modern design, featuring an oven, microwave, and window.

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

9.6 out of 10, Exceptional, (50)
"We loved the Wee House. It was great at the end of the day to sit on the porch, listen to the birds, and watch the barges on the river. The kitchen had everything we needed. We especially liked the quilts on the beds--so cheerful and colorful. And the location was perfect--just two short blocks from Main Street so we could walk everywhere."
The Wee House is a shotgun house that is remodeled with a view of the Ohio river
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
Set within a brick wall, this charming entrance features a decorative wreath and a welcoming doormat.

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

10.0 out of 10, Exceptional, (24)
"The house was clean, great location. Would stay again"
The price is AU$394
includes taxes & fees
4 Aug - 5 Aug
The Hanover Hideaway! Minutes from Hanover College, 5 Miles to Downtown Madison!
East End River Retreat: Dogs Welcome!
Enjoy cooking and dining in this classic kitchen with a central island, sink, and countertop, connected to a dining area with a table and chairs.

East End River Retreat: Dogs Welcome!

10.0 out of 10, Exceptional, (8)
"We had a lovely time. Great property with easy access to everything. Our kids loved the golf cart and we appreciated the extra touches from the owners. Great little house for a stay in a great little town."
East End River Retreat: Dogs Welcome!
Relaxing Country Getaway
Cozy space with a fireplace, leather sofa, and wooden panel walls, perfect for relaxing.

Relaxing Country Getaway

9.4 out of 10, Exceptional, (34)
"Wonderful stay, very private. Cozy place perfect for couples looking to unwind. Would stay again."
Relaxing Country Getaway
The Wadsworth in National Historic District of Madison, Indiana.
Enjoy cooking in this well-equipped kitchen with an oven and stovetop.

The Wadsworth in National Historic District of Madison, Indiana.

10.0 out of 10, Exceptional, (51)
"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!!
Traditional home with a symmetrical facade, featuring a decorative front door and a small porch area.

Bungalow on Main!!

9.8 out of 10, Exceptional, (15)
"This place was great. The wife and I need a little getaway to relax and recharge. Our stay here was perfect for that. Nice amenities and the private hottub was really relaxing. Will definitely book here again. "
Bungalow on Main!!
Modern Nature Cabin | Private Escape in the Forest
Fridge, microwave, oven, stovetop

Modern Nature Cabin | Private Escape in the Forest

10.0 out of 10, Exceptional, (1)
"Very nice place, the hike to the falls was pretty neat as well. Close to everything, yet still secluded. "
The price is AU$365
includes taxes & fees
14 Aug - 15 Aug
Modern Nature Cabin | Private Escape in the Forest
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Enjoy cooking in this well-equipped kitchen with a stove, oven, and microwave.

Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown

10.0 out of 10, Exceptional, (47)
"Awesome home in a great location! Very well done inside with unique features and lots of room. "
Luxurious 4 Bedroom Home in Heart of Historic Madison's Downtown
Secluded Country Home in Historic Hoosier Hills
Enjoy a meal al fresco in this serene outdoor dining area, complete with a beautifully set table and lush surroundings.

Secluded Country Home in Historic Hoosier Hills

10.0 out of 10, Exceptional, (118)
"Great property, very peaceful. "
Secluded Country Home in Historic Hoosier Hills
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!
Kitchen features stainless steel appliances, a wooden cutting board, and ample counter space for food preparation.

Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!

10.0 out of 10, Exceptional, (24)
"Great place. "
Grand Fireplace at the Heart of the Home! Updates Galore, but lots of Old Charm!
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Fully equipped kitchen with microwave, stove, sink, and refrigerator.

Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St

10.0 out of 10, Exceptional, (5)
"My husband and I came to celebrate our anniversary and his retirement and to go hiking- our favorite activity together! This place was perfect! Location! Location! Location! Near everything- walked downtown to shops and restaurants! The place itself was clean, nicely decorated, and very welcoming We will e back! "
Riverside Retreat ~ One Story ~ 3bd/2ba ~ Steps to the River & Main St
Emerald Lake Retreat Charlestown
Property grounds

Emerald Lake Retreat Charlestown

10.0 out of 10, Exceptional, (1)
"Excellent communication, fast responses, very accommodating. The layout is fantastic with lots of open space, comfortable bedrooms, and excellent amenities. The backyard is absolutely huge, probably 3 acres or so. Would stay again for sure."
Emerald Lake Retreat Charlestown
The Artist’s A-Frame
Enjoy a view of the surrounding greenery from the large window.

The Artist’s A-Frame

10.0 out of 10, Exceptional, (14)
"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 AU$361
includes taxes & fees
6 Aug - 7 Aug
The Artist’s A-Frame
Madison's Only YURT Experience
Exposed wooden beams and a rustic wooden table set the tone in this cozy space with a ladder leading to a higher level.

Madison's Only YURT Experience

9.4 out of 10, Exceptional, (8)
"Better than we expected! Lots of land for the kids to explore. The goats were so fun to watch. Fishing at the pond was a nice surprise. We loved the bottle of wine waiting for us! It was such a unique getaway! Great family trip!"
Madison's Only YURT Experience
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
Kitchen features a stainless steel range, microwave, and small sink with a countertop.

Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!

10.0 out of 10, Exceptional, (6)
"This was such a nice place, very quiet and peaceful. The property was everything we had hoped for and the host was so nice and helpful."
Candlelit Comfort: Hot Tub, Firepit, Massage Chair-Romantic Getaway!
Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
Relax by the fire pit in a serene backyard setting with a seating area and pathway.

Beautiful and spacious 3BR historic home centrally located in downtown, Madison.

10.0 out of 10, Exceptional, (44)
"We had a great stay and the communication was terrific. Thanks SW"
Beautiful and spacious 3BR historic home centrally located in downtown, Madison.
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
Enjoy al fresco dining on the patio with a grill and scenic views.

The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!

10.0 out of 10, Exceptional, (42)
"Prefect accommodations for a weekend getaway. A beautiful space, friendly owners, and a private setting."
The Cypress Grove Inn ~Madison, IN!<br>*5 Star hosts!
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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