Middletown Vacation Rentals from ￥28,541: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Middletown?

Modern Bungalow Home with Mid-Century Flair : Visitors like this Middletown vacation home rental. It offers a garden, a barbecue grill, 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 you can cook with friends or family.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Middletown vacation rentals

A cozy interior with a staircase, leather sofas, a chandelier, and bookshelves filled with books and decorative items.

1. Lincoln’s Loft - Speakeasy Suite

Lincoln

Kyle O.

￥35,633 total

includes taxes & fees

Oct 5 - Oct 6

A living room with a brown leather sofa, a city-themed pillow, a kitchen with modern appliances, and a loft-style ceiling.

2. Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL

Lincoln

Sean W.

￥38,159 total

includes taxes & fees

Oct 5 - Oct 6

A carpeted staircase with a handrail, a door with a number plate, and a light fixture on the ceiling.

3. "Living on the Wedge" A 3-bedroom house in Lincoln on Historic Route 66.

Lincoln

"The place was very clean and spacious. It is decorated Mid Century Modern. 2nd floor is the main floor.We loved the 3rd floor media room where many channels were available to watch/stream. Paddington Bear was watching atop his suit case. There is a half bath on 3rd floor if the need arises while watching shows.The bathrooms were cute. I meant to take pictures. The master bedrooms bathroom had a blue tub and cute pattern wall paper.We slept well.We were in town for our grandson's soccer...

Carol S.

￥58,217 total

includes taxes & fees

Oct 6 - Oct 7

A kitchen with wooden cabinets, a dining area with a table and chairs, and a television in the background.

4. Modern Bungalow Home with Mid-Century Flair

Springfield

Diane

￥35,800 total

includes taxes & fees

Oct 12 - Oct 13

A two-story Victorian-style house with a wrap-around porch, a prominent tower with a conical roof, and a well-maintained front yard with flowering plants.

5. Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

Springfield

Joseph

￥28,541 total

includes taxes & fees

Oct 5 - Oct 6

A large, historic brick building with a prominent tower and arched windows, surrounded by well-maintained lawns and trees.

6. Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

Springfield

Lynn

￥36,495 total

includes taxes & fees

Oct 25 - Oct 26

7. Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Springfield

Rebecca k.

￥36,585 total

includes taxes & fees

Oct 7 - Oct 8

A large, historic brick building with a turret and multiple windows, surrounded by a well-maintained lawn and a metal fence.

8. Spacious Carriage House | Private Entrance | Historic & Stylish

Springfield

Christine

￥35,690 total

includes taxes & fees

Oct 5 - Oct 6

View all properties

Find vacation rentals that suit your style

Apartments

Condos

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Middletown Hotel Reviews

Inn at 835 Boutique Hotel

10/10 Excellent

"It’s a wonderful historical property with lots of charm. Staff is very friendly and helpful. The breakfast is more than the average hotel breakfast being served individually. The room was clean and had everything I needed. It even had a shared balcony."

Microtel Inn & Suites by Wyndham Springfield

8/10 Good

"The room was nice. The only thing was there was a strange smell. It wasn’t anything unbearable but just a little different. The staff was helpful and helped us get out of a jam with our previous hotel, so all things considered we really enjoyed our stay."

Americas Best Value Inn Springfield - Mansion View

10/10 Excellent

"This is a fantastically located downtown motel that is very much a work in progress. If you think its location across the street from the governor’s mansion (yes, literally) means a high end or expensive hotel, keep dreaming. It’s old, fell into disrepair along with other parts of the neighborhood, and yet still has so much to offer. The (newer, 1 to 3 years??) owners not only care about their business and customers but also their neighbors and neighborhood. They don’t publicize their charitable activities but if you directly ask the owner you can learn more. Renovations are a huge and complicated task so expect old flooring, peeling paint, etc. Everything is working and if you have an issue it’ll be dealt with promptly but the lower rates are because they are doing the work themselves & not just bringing in contractors to do the upgrades quickly so they can double or triple their rates. The location is walkable to everything in downtown Springfield - all tourist / Lincoln stuff, all government buildings, entertainment, restaurants, etc. I have felt safe in the area whether it’s noon or midnight (bear in mind I am male!). Parking is good, the rooms and property are clean but old, and you WILL ABSOLUTELY hear the trains at night when they past the backside of the building. I’m a very sound sleeper & have no noise complaints but if you’re a light sleeper you may need to stay elsewhere. Double the quiet, double the $$. Just be aware, & ask questions, they’re honest and upfront"

Find out more about Middletown

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

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

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

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we offer vacation rentals close to well known sights in Middletown, or you can choose a more secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Middletown?

Modern Bungalow Home with Mid-Century Flair: Visitors like this Middletown vacation home rental. It offers a garden, a barbecue grill, 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 you can cook with friends or family.

What’s there to see and do in Middletown?

While exploring the area, visit the sights like World's Largest Railsplitter Covered Wagon, Lincoln Speedway, and Lincoln's New Salem State Historic Site. In the larger area, you’ll find Illinois State Fairgrounds and Lincoln's Tomb.

What are vacation rentals like in Middletown?

Vacation rentals are private properties you can reserve for a couple days or more in Middletown. Vacation rentals offer amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middletown vacation rentals

1. Lincoln’s Loft - Speakeasy Suite

2. Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL

3. "Living on the Wedge" A 3-bedroom house in Lincoln on Historic Route 66.

4. Modern Bungalow Home with Mid-Century Flair

5. Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

6. Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

7. Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

8. Spacious Carriage House | Private Entrance | Historic & Stylish

9. The coolest most fun house with pool hot tub pool table air hockey and much more

10. Historic Luxury Stay | Downtown Springfield | Step-Free Access

11. Charming Downtown Stay | Victorian Beauty & Modern Comfort

12. Top-Rated Premier Modern Getaway

13. Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!

14. Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance

15. Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks

16. Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

Find vacation rentals that suit your style

Top Middletown Hotel Reviews

Inn at 835 Boutique Hotel

Northfield Inn, Suites & Conference Center

Travelodge by Wyndham Atlanta, Illinois

Riverbank Lodge

Days Inn by Wyndham Lincoln, IL/Route 66

Microtel Inn & Suites by Wyndham Springfield

Ramada by Wyndham Springfield North

Super 8 by Wyndham Lincoln

Americas Best Value Inn Springfield - Mansion View

Find out more about Middletown

Frequently asked questions

Go further with the Expedia app