Book Holiday Homes in Milton

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Featured Holiday Homes in Milton

Entire Home with Modern Conveniences - New Castle

Entire Home with Modern Conveniences - New Castle

New Castle IN
The price is AU$362 per night from 14 Jan to 15 Jan
AU$362
14 Jan - 15 Jan 2026
includes taxes & fees
Located in New Castle, this vacation home is within a 5-minute drive of Indiana Basketball Hall of Fame and Trojan Woods Nature Preserve.
Opens in a new windowEntire Home with Modern Conveniences - New Castle
Secluded lake house on 6 acres, with trails and easy access to Brookville Lake.

Secluded lake house on 6 acres, with trails and easy access to Brookville Lake.

Brookville IN
Located in Brookville, this vacation home is on the waterfront, within a 5-minute drive of Mounds State Recreation Area and Brookville Lake.
Opens in a new windowSecluded lake house on 6 acres, with trails and easy access to Brookville Lake.
Hot Tub Arcadia - Relax and Play

Hot Tub Arcadia - Relax and Play

Greensboro IN
The price is AU$398 per night from 15 Jan to 16 Jan
AU$398
15 Jan - 16 Jan 2026
includes taxes & fees
Located in New Castle, this vacation home is in a rural location, within a 10-minute drive of Westwood Park Reservoir and Westwood Park.
Opens in a new windowHot Tub Arcadia - Relax and Play
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Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!

Richmond IN
The price is AU$501 per night from 5 Jan to 6 Jan
AU$501
5 Jan - 6 Jan 2026
includes taxes & fees
Located in Richmond, this vacation home is within a 5-minute drive of Glenn Miller Park and Rose Garden.
Opens in a new windowCharming Home! Prime Location! Dog-Friendly!
Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park

Richmond IN
The price is AU$270 per night from 25 Dec to 26 Dec
AU$270
25 Dec - 26 Dec
includes taxes & fees
With a stay at this vacation home in Richmond, you'll be a 1-minute walk from Glenn Miller Park and 8 minutes by foot from Rose Garden.
Opens in a new windowBoho Bungalow off Main-one block from Lovely Park
Recently remodeled Colonial-style home with room for the whole family!

Recently remodeled Colonial-style home with room for the whole family!

Richmond IN
Located in Richmond, this vacation home is within a 5-minute drive of Glenn Miller Park and Rose Garden.
Opens in a new windowRecently remodeled Colonial-style home with room for the whole family!
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

Greens Fork IN
A stay at this vacation home places you in the heart of Greens Fork, a 3-minute drive from Clay Township Historical Museum and 10 minutes from Warm Glow Candle ...
Opens in a new windowStunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Elegant 1BR, Workspace, Near Parks and Summit Lake

Elegant 1BR, Workspace, Near Parks and Summit Lake

New Castle IN
With a stay at this vacation home in New Castle, you'll be a 2-minute walk from Courthouse Square and 7 minutes by foot from Henery County Arts Park.
Opens in a new windowElegant 1BR, Workspace, Near Parks and Summit Lake
The Hidden Gem in downtown Connersville

The Hidden Gem in downtown Connersville

Connersville IN
The price is AU$1,054 per night from 26 Dec to 27 Dec
AU$1,054
26 Dec - 27 Dec
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Connersville, just a 3-minute walk from Whitewater Valley Railroad and 10 minutes by foot from ...
Opens in a new windowThe Hidden Gem in downtown Connersville
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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.

Milton Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Milton vacation homes are the perfect way for you to wing it.

Holiday houses in Milton let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Milton in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Milton adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Milton with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Milton vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Milton Holiday Homes essential information

Accommodation
27 Holiday Homes
Lowest Price
AU$86
Highest Price
AU$1,054
Popular accommodation
Entire Home with Modern Conveniences - New Castle, Secluded lake house on 6 acres, with trails and easy access to Brookville Lake., Hot Tub Arcadia - Relax and Play, Charming Home! Prime Location! Dog-Friendly!, Boho Bungalow off Main-one block from Lovely Park, Recently remodeled Colonial-style home with room for the whole family!, Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting., Elegant 1BR, Workspace, Near Parks and Summit Lake, The Hidden Gem in downtown Connersville

Top trending hotels in Milton

Family-friendly Milton Home on 14 Acres w/ Hot Tub

Family-friendly Milton Home on 14 Acres w/ Hot Tub

3 out of 5
Milton IN
With a stay at this cottage in Milton, you'll be 8.9 mi (14.3 km) from Scout Lake and 11 mi (17.7 km) from Abbott's Candy Shop.
Opens in a new windowFamily-friendly Milton Home on 14 Acres w/ Hot Tub
Baymont by Wyndham Richmond I-70

Baymont by Wyndham Richmond I-70

2.5 out of 5
912 Mendleson Dr Richmond IN
Fully refundableReserve now, pay when you stay
The price is AU$112 per night from 26 Dec to 27 Dec
AU$112
26 Dec - 27 Dec
includes taxes & fees
When you stay at Baymont by Wyndham Richmond I-70 in Richmond, you'll be near the airport, within a 15-minute walk of Indiana University East and Reid Hospital ...
Opens in a new windowBaymont by Wyndham Richmond I-70
Motel 6 Richmond, IN

Motel 6 Richmond, IN

2 out of 5
6030 National Road East Richmond IN
Fully refundableReserve now, pay when you stay
The price is AU$86 per night from 7 Jan to 8 Jan
AU$86
7 Jan - 8 Jan 2026
includes taxes & fees
With a stay at Motel 6 Richmond, IN in Richmond, you'll be within a 5-minute drive of Old National Road Welcome Center and Richmond Mall.
Opens in a new windowMotel 6 Richmond, IN
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Comfort Suites

Comfort Suites

2.5 out of 5
421 Commerce Road Richmond IN
Fully refundableReserve now, pay when you stay
The price is AU$158 per night from 11 Jan to 12 Jan
AU$158
11 Jan - 12 Jan 2026
includes taxes & fees
When you stay at Comfort Suites Richmond East in Richmond, you'll be in the historical district, within a 5-minute drive of Old National Road Welcome Center ...
Opens in a new windowComfort Suites
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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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^Subject to availability and chosen travel dates.