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Milton Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Milton holiday rentals

Games room

1. The Hidden Gem in downtown Connersville

The Hidden Gem in downtown Connersville
Connersville
10.0 out of 10, Exceptional, (27 reviews)
"Great place for friends to gather. "
United States
Leslie P.
The price is HK$3,530
HK$5,527 total
includes taxes & fees
20 Sept - 21 Sept
The Hidden Gem in downtown Connersville
Coffee/tea maker, fridge, microwave, oven

2. Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+

Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Hagerstown
10.0 out of 10, Exceptional, (18 reviews)
"This is a darling place in a wonderful town. It met all of our needs and we'll definitely stay here again."
United States
Tamera
The price is HK$558
HK$1,284 total
includes taxes & fees
29 Sept - 30 Sept
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
Coffee/tea maker, fridge, microwave, oven

3. New Hagerstown Apartment - Self Check-in. Sleeps 4+

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.4 out of 10, Exceptional, (27 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
United States
Emily E.
The price is HK$551
HK$1,188 total
includes taxes & fees
23 Sept - 24 Sept
New Hagerstown Apartment - Self Check-in. Sleeps 4+
Interior

4. Woodland Retreat w/ Game Room, Fire Pit & King Suite

Woodland Retreat w/ Game Room, Fire Pit & King Suite
Greens Fork
8.8 out of 10, Excellent, (18 reviews)
"Great location for Hwy 127 garage sale "
United States
Margaret G.
The price is HK$2,745
HK$5,236 total
includes taxes & fees
21 Sept - 22 Sept
Woodland Retreat w/ Game Room, Fire Pit & King Suite
3 bedrooms, desk, iron/ironing board, free WiFi

5. Spacious 3 Bedroom Home - New Castle

Spacious 3 Bedroom Home - New Castle
New Castle
9.8 out of 10, Exceptional, (17 reviews)
"Host were very helpful. The house was clean and well stocked."
United States
Lodi R.
The price is HK$1,153
HK$2,132 total
includes taxes & fees
20 Sept - 21 Sept
Spacious 3 Bedroom Home - New Castle
Property grounds

6. Enter As Strangers Leave As Friends

Enter As Strangers Leave As Friends
Lewisville
10.0 out of 10, Exceptional, (48 reviews)
"The house was adorable with a lot of games, books and movies. The host was very friendly and helpful. "
United States
SUZANN S.
The price is HK$1,765
HK$2,214 total
includes taxes & fees
27 Sept - 28 Sept
Enter As Strangers Leave As Friends
TV

7. Cozy 1 Bedroom Apartment

Cozy 1 Bedroom Apartment
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"We absolutely enjoyed our stay!!"
United States
Auren
The price is HK$839
HK$1,543 total
includes taxes & fees
21 Sept - 22 Sept
Cozy 1 Bedroom Apartment
Exterior

8. Charming Home! Prime Location! Dog-Friendly!

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (20 reviews)
"The host was awesome and completely goes the extra mile! "
United States
Rondaq C.
The price is HK$1,236
HK$2,588 total
includes taxes & fees
1 Oct - 2 Oct
Charming Home! Prime Location! Dog-Friendly!
Interior

9. Entire Home with Modern Conveniences - New Castle

Entire Home with Modern Conveniences - New Castle
New Castle
10.0 out of 10, Exceptional, (26 reviews)
"Had everything we needed. Well kept and clean. Great place for a stay!"
United States
Tricia V.
The price is HK$996
HK$1,879 total
includes taxes & fees
25 Sept - 26 Sept
Entire Home with Modern Conveniences - New Castle
Interior

10. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (41 reviews)
"This is a wonderful historic property if you're into a vintage stay. We were. The home is lovely. The only disadvantages are not having a host on-site and having to get luggage up the stairs without an elevator or bellhop assitance; there are no bedrooms on the ground floor. And being vintage, it takes quite a while to adjust the temperature to where you want it. Also, it would be helpful to have television instructions; we were never able to figure out how to get anything on the TV."
United States
Debbie
The price is HK$1,294
HK$2,601 total
includes taxes & fees
21 Sept - 22 Sept
Westcott Mansion with Pickleball Court & Huge Gazebo
Smart TV, books

11. Quaker Hill Cottage on gated estate with fire pit & hiking trails

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.4 out of 10, Exceptional, (36 reviews)
"Very nice place to spend the night while passing through on Route 70. The Thistlethwaite Falls are only minutes away and were a perfect evening activity after driving all day."
United States
Jon and Keri C.
The price is HK$902
HK$1,748 total
includes taxes & fees
21 Sept - 22 Sept
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Interior

12. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is HK$800
HK$2,508 total
includes taxes & fees
20 Sept - 21 Sept
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Smart TV, books

13. Downtown New Castle Indiana Condo for short-and long-term stays. Very popular.

Downtown New Castle Indiana Condo for short-and long-term stays. Very popular.
New Castle
10.0 out of 10, Exceptional, (41 reviews)
"Great stay "
United States
Craig Z.
The price is HK$812
HK$1,674 total
includes taxes & fees
24 Sept - 25 Sept
Downtown New Castle Indiana Condo for short-and long-term stays. Very popular.
TV

14. Pets Welcome! Quiet Economy Home w/ Spacious Yard

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
2.0 out of 10, (1 review)
"Bed bugs in upstairs bedroom!!!Unfortunately we had a terrible experience both during and following our stay. During the stay the air conditioning was not functioning properly and we were forced to use portable AC units that didn’t get the temperature below 78 in the house.Three people sleeping upstairs had bed bug bites and upon searching the two beds we found numerous bugs. We promptly made the property owner aware of the situation and requested our stay be refunded due to the inconvenience...
United States
Payton L.
The price is HK$565
HK$2,583 total
includes taxes & fees
20 Sept - 21 Sept
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Interior

15. 18 Acre Farm - Pickleball, Pond, Outdoor Kitchen

18 Acre Farm - Pickleball, Pond, Outdoor Kitchen
Wayne Township
10.0 out of 10, Exceptional, (11 reviews)
"Super week stay a very unique well equipped house - From the inside kitchen to the outdoor kitchen and grilling area plus wildlife galore, nothing is better then eating breakfast and deers show up and pose outside the windows The house is fitted in a retro style with modern amenities. Would definitely stay there again"
United States
Robin A.
The price is HK$3,146
HK$6,369 total
includes taxes & fees
20 Sept - 21 Sept
18 Acre Farm - Pickleball, Pond, Outdoor Kitchen
Private kitchen

16. Hannah's Creek Farm Cottage

Hannah's Creek Farm Cottage
Liberty
9.8 out of 10, Exceptional, (8 reviews)
"Lovely host, and beautiful location. We enjoyed the quiet away from town a lot."
United States
Melissa H.
The price is HK$981
HK$1,362 total
includes taxes & fees
24 Sept - 25 Sept
Hannah's Creek Farm Cottage
1 bedroom

17. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (115 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveller
The price is HK$514
HK$656 total
includes taxes & fees
20 Sept - 21 Sept
2 Queen Beds Non-Smoking
Dining

18. King Bed Non-Smoking

King Bed Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (152 reviews)
"The staff were friendly and helpful throughout our stay. It felt welcoming right away."
United States
Anonymous traveller
The price is HK$480
HK$611 total
includes taxes & fees
20 Sept - 21 Sept
King Bed Non-Smoking
Interior

19. Cozy 1-bedroom apartment in a 160 year old historic downtown location.

Cozy 1-bedroom apartment in a 160 year old historic downtown location.
New Castle
9.8 out of 10, Exceptional, (9 reviews)
"As a veteran, I was excited to discover that it was veteran owned!"
United States
Robin
The price is HK$745
HK$1,300 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 1-bedroom apartment in a 160 year old historic downtown location.
Living area

20. Boho Bungalow off Main-one block from Lovely Park

Boho Bungalow off Main-one block from Lovely Park
Richmond
9.0 out of 10, Wonderful, (19 reviews)
"The house is very clean and nicely appointed. Owner is quick to respond to messages. We would definitely stay here again."
United States
Joanne K.
Boho Bungalow off Main-one block from Lovely Park
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

Motel 6 Richmond, IN

Motel 6 Richmond, IN

8/10 Good
"Staff was very kind. Room was clean and met our needs. Only suggestion is better blankets, only a very thin bedspread was provided."
Fawn 1-night trip
Posted 13 hours ago
Motel 6 Richmond, IN

Find out more about Milton

Search for holiday rentals in Milton on Expedia! You can easily find your home rentals, villas, holiday apartments in Milton using one of the methods below:

  • View our selection of featured holiday rentals in Milton
  • Use the map to find apartments and other holiday homes in the Milton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Milton while they last

Look no further and take a look at our great range of rental properties in Milton!

Frequently asked questions

Can I find a holiday rental 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?

Woodland Retreat w/ Game Room, Fire Pit & King Suite: This holiday home rental outside of Milton offers a pool table, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Milton?

Choose from 3 Expedia holiday rentals in Milton for a memorable holiday.

What’s there to see and do in Milton?

Explore the area and family-friendly sights such as Warm Glow Candle Company, or get out into nature at a spot like Glenn Miller Park. Whitewater Valley Railroad and Wayne County Fairgrounds are a couple of places you'll find in the wider area.

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 extras such as WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a small group gathering.