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Milton Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Milton vacation rentals

A kitchen with wooden cabinets, a stainless steel stove, and a refrigerator.

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

New Hagerstown Apartment - Self Check-in. Sleeps 4+
Hagerstown
9.4 out of 10, Exceptional, (28 reviews)
"Great location and just what we needed for a relaxing weekend in Hagerstown."
United States
Emily E.
The price is CA $86
CA $185 total
includes taxes & fees
Nov 17 - Nov 18
New Hagerstown Apartment - Self Check-in. Sleeps 4+
A modern kitchen with stainless steel appliances, wooden cabinets, and a white tiled backsplash.

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 CA $111
CA $229 total
includes taxes & fees
Dec 1 - Dec 2
Charming small town experience in Hagerstown, Indiana, self check-in, sleeps 5+
A living room with a blue sofa, a small round table, a floor lamp, a potted plant, and a patterned rug.

3. 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 CA $150
CA $261 total
includes taxes & fees
Nov 10 - Nov 11
Cozy 1 Bedroom Apartment
A hotel lobby with a reception desk, a dining area with round tables and chairs, a kitchen area, and a window with a view.

4. King Bed Non-Smoking

King Bed Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (154 reviews)
"The staff were friendly and helpful throughout our stay. It felt welcoming right away."
United States
Anonymous traveller
The price is CA $74
CA $96 total
includes taxes & fees
Nov 7 - Nov 8
King Bed Non-Smoking
A modern kitchen with dark cabinetry, a wooden countertop, and a built-in stove. There is a seating area with a green sofa and a small table.

5. 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, (12 reviews)
"Very nice property. Will stay again."
United States
Jason M.
The price is CA $133
CA $231 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom apartment in a 160 year old historic downtown location.
A hotel room with two beds, a small table, a mirror, and a bathroom with a sink and toilet.

6. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richmond IN
9.8 out of 10, Exceptional, (119 reviews)
"Loved how cozy and inviting this place felt!"
United States
Anonymous traveller
The price is CA $81
CA $105 total
includes taxes & fees
Nov 7 - Nov 8
2 Queen Beds Non-Smoking
Interior

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
3.0 star property
Economy
The price is CA $151
CA $457 total
includes taxes & fees
Nov 14 - Nov 15
Pets Welcome! Quiet Economy Home w/ Spacious Yard
Living area

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

Pets Welcome! Quiet Economy Home w/ Spacious Yard
Economy
6.0 out of 10, (2 reviews)
"Our second stay for a family cemetery project.Nice safety improvements since we visited - a railing on the steps to the second floor, a grab bar and mat for the tub.The atmosphere feels homey despite some quirks as a result of the home’s age.Easy stay."
United States
Robert Toy
The price is CA $108
CA $442 total
includes taxes & fees
Nov 14 - Nov 15
Pets Welcome! Quiet Economy Home w/ Spacious Yard
A living room with a flat-screen TV mounted on the wall, a dark console table with decorative items, a wicker basket with a book, and a large potted plant.

9. Entire Home with Modern Conveniences - New Castle

Entire Home with Modern Conveniences - New Castle
New Castle
10.0 out of 10, Exceptional, (28 reviews)
"Had everything we needed. Well kept and clean. Great place for a stay!"
United States
Tricia V.
The price is CA $178
CA $318 total
includes taxes & fees
Dec 5 - Dec 6
Entire Home with Modern Conveniences - New Castle
A large indoor swimming pool with multiple lounge chairs and a changing room.

10. 2 Queen Beds | Non-Smoking

2 Queen Beds | Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $84
CA $93 total
includes taxes & fees
Nov 5 - Nov 6
2 Queen Beds | Non-Smoking
A modern living room with a grey sectional sofa, a small wooden coffee table, and a dining area with a bar.

11. 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 CA $151
CA $301 total
includes taxes & fees
Nov 10 - Nov 11
Downtown New Castle Indiana Condo for short-and long-term stays. Very popular.
A modern living room with a sofa, armchair, and a white spiral staircase.

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

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Richmond
9.2 out of 10, Wonderful, (39 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 CA $161
CA $296 total
includes taxes & fees
Nov 16 - Nov 17
Quaker Hill Cottage on gated estate with fire pit & hiking trails
A rustic kitchen with wooden beams, a sink, a refrigerator, and a window with curtains.

13. Hannah's Creek Farm Cottage

Hannah's Creek Farm Cottage
Liberty
9.8 out of 10, Exceptional, (9 reviews)
"Lovely host, and beautiful location. We enjoyed the quiet away from town a lot."
United States
Melissa H.
The price is CA $175
CA $230 total
includes taxes & fees
Nov 7 - Nov 8
Hannah's Creek Farm Cottage
A bedroom with a bed, a bench, a rug, and a wall-mounted painting.

14. Spacious 3 Bedroom Home - New Castle

Spacious 3 Bedroom Home - New Castle
New Castle
9.8 out of 10, Exceptional, (17 reviews)
"The hosts were very accommodating. We enjoyed our stay and highly recommend to others."
United States
Nathaniel P.
The price is CA $206
CA $364 total
includes taxes & fees
Nov 17 - Nov 18
Spacious 3 Bedroom Home - New Castle
A wooden swing set in a grassy area with houses in the background.

15. Enter As Strangers Leave As Friends

Enter As Strangers Leave As Friends
Lewisville
10.0 out of 10, Exceptional, (51 reviews)
"Great communication. Great place to stay.I would stay there again."
United States
Shawn J.
The price is CA $315
CA $384 total
includes taxes & fees
Nov 10 - Nov 11
Enter As Strangers Leave As Friends
A grand staircase with ornate wooden railings and a decorative balustrade, leading to a room with large stained glass windows and a chandelier.

16. Westcott Mansion with Pickleball Court & Huge Gazebo

Westcott Mansion with Pickleball Court & Huge Gazebo
Richmond
9.8 out of 10, Exceptional, (41 reviews)
"We had the best time. House was gorgeous and unique. Perfect place for our group as everyone had their own room and their own bed! Would absolutely stay here again. "
United States
Megan H.
The price is CA $231
CA $439 total
includes taxes & fees
Nov 16 - Nov 17
Westcott Mansion with Pickleball Court & Huge Gazebo
A two-story house with a steeply pitched roof, a yellow front door, and a number '405' on the side.

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

Charming Home! Prime Location! Dog-Friendly!
Richmond
9.8 out of 10, Exceptional, (22 reviews)
"Great house in beautiful neighborhood."
United States
Chad H.
The price is CA $190
CA $408 total
includes taxes & fees
Nov 9 - Nov 10
Charming Home! Prime Location! Dog-Friendly!
A large indoor swimming pool with multiple lounge chairs and a tiled floor.

18. 1 QUEEN BED | BUSINESS, NON-SMOKING

1 QUEEN BED | BUSINESS, NON-SMOKING
Richmond IN
10.0 out of 10, Exceptional, (4 reviews)
"Would book again without hesitation if passing through Charlotte. Easy access, comfy bed, quick snack options kept it simple and good."
United States
Anonymous traveller
The price is CA $84
CA $93 total
includes taxes & fees
Nov 5 - Nov 6
1 QUEEN BED | BUSINESS, NON-SMOKING
A large indoor swimming pool with multiple lounge chairs and a changing room.

19. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Richmond IN
10.0 out of 10, Exceptional, (2 reviews)
"Evenings spent by the pool were very relaxing, perfect way to unwind after busy days."
United States
Anonymous traveller
The price is CA $84
CA $93 total
includes taxes & fees
Nov 5 - Nov 6
1 King Bed | Non-Smoking
A wooden bar area with a pool table, a mirror, and a sink.

20. The Hidden Gem in downtown Connersville

The Hidden Gem in downtown Connersville
Connersville
10.0 out of 10, Exceptional, (27 reviews)
"The house was fantastic. Very clean, lots of beautiful Nick nacks and such a great host!"
United States
Daniel P.
The price is CA $629
CA $935 total
includes taxes & fees
Nov 10 - Nov 11
The Hidden Gem in downtown Connersville
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

Fairfield Inn by Marriott Richmond

Fairfield Inn by Marriott Richmond

10/10 Excellent
"Nice property"
Richard 1-night trip
Posted 2 hours ago
Fairfield Inn by Marriott Richmond

Find out more about Milton

Everything you need to know about Milton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Milton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Milton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Milton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Milton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Milton vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Milton vacation rentals we have selected for you start as low as CA $105 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Milton rentals

At Expedia, we put the best Milton vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Milton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Milton vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Milton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a vacation rental in Milton?

Yes, you can find vacation rentals close to top sights in Milton, or you can select a more secluded option if you'd like a relaxing place to stay.

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

Secluded lake house on 6 acres, with trails and easy access to Brookville Lake.: Visitors like this Milton vacation home rental. It is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Milton?

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

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 Middlefork Reservoir Park. Whitewater Valley Railroad and Wayne County Fairgrounds are a couple of places you'll find in the larger area.

What are vacation rentals like in Milton?

Vacation rentals are private properties you can book for a couple days or more in Milton. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.