Middletown Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middletown vacation rentals

Wednesday’s Lair - Lincoln, Il

Wednesday’s Lair - Lincoln, Il
Lincoln
10.0 out of 10, Exceptional, (11 reviews)
"Had a blast!"
United States
Abby R.
The price is CA $216
CA $473 total
includes taxes & fees
May 18 - May 19
Wednesday’s Lair - Lincoln, Il

Lincoln’s Loft - Speakeasy Suite

Lincoln’s Loft - Speakeasy Suite
Lincoln
10.0 out of 10, Exceptional, (54 reviews)
"Host was great evereas as it said. Unique place to stay not alot to day in town but thus was a family trip we had a great time with the board games and cute little creamery within walking distance."
United States
melissa l.
The price is CA $189
CA $290 total
includes taxes & fees
May 28 - May 29
Lincoln’s Loft - Speakeasy Suite

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

"Living on the Wedge" A 3-bedroom house in Lincoln on Historic Route 66.
Lincoln
The price is CA $308
CA $488 total
includes taxes & fees
May 17 - May 18
"Living on the Wedge" A 3-bedroom house in Lincoln on Historic Route 66.

Charming Springfield Home: 2 Mi to Downtown

Charming Springfield Home: 2 Mi to Downtown
3.0 star property
Springfield
10.0 out of 10, Exceptional, (2 reviews)
"The cottage was nicely renovated and decorated. It had a good supply of necessities and very comfortable!"
United States
Amie
The price is CA $95
CA $337 total
includes taxes & fees
May 25 - May 26
Charming Springfield Home: 2 Mi to Downtown

Modern Bungalow Home with Mid-Century Flair

Modern Bungalow Home with Mid-Century Flair
Springfield
8.4 out of 10, Very good, (55 reviews)
"Second year using this house while in town. Great accommodations for the price. The only thing this time were the smoke detectors needed some attention. "
United States
Shannon E.
The price is CA $144
CA $305 total
includes taxes & fees
May 17 - May 18
Modern Bungalow Home with Mid-Century Flair

Historic Luxury Stay | Downtown Springfield | Step-Free Access

Historic Luxury Stay | Downtown Springfield | Step-Free Access
Springfield
10.0 out of 10, Exceptional, (9 reviews)
"Great place to stay ! Close to all things Lincoln. "
United States
Patricia J.
The price is CA $228
CA $260 total
includes taxes & fees
May 17 - May 18
Historic Luxury Stay | Downtown Springfield | Step-Free Access

Spacious Carriage House | Private Entrance | Historic & Stylish

Spacious Carriage House | Private Entrance | Historic & Stylish
Springfield
9.8 out of 10, Exceptional, (45 reviews)
"All of the above!The location and setting of the Carriage House are perfect, and I love the feel with the antiques - as if I had stepped back in time! Of course, it also had all of the necessary modern amenities!"
United States
Brenda B.
The price is CA $282
CA $325 total
includes taxes & fees
May 17 - May 18
Spacious Carriage House | Private Entrance | Historic & Stylish

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Springfield
9.6 out of 10, Exceptional, (23 reviews)
"Had a wonderful time with friends and family it was a very lovely place "
United States
Ava A.
The price is CA $301
CA $347 total
includes taxes & fees
May 20 - May 21
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

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

Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
Springfield
9.2 out of 10, Wonderful, (9 reviews)
"George is an awesome host! Our group of high schoolers love this place! Plenty to keep them busy and engaged!"
United States
Ann P.
The price is CA $1,302
CA $1,811 total
includes taxes & fees
May 15 - May 16
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!

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

Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort
Springfield
10.0 out of 10, Exceptional, (15 reviews)
"Great stay, everything was clean and plenty of space. "
United States
Lindsay S.
The price is CA $252
CA $288 total
includes taxes & fees
Jun 1 - Jun 2
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

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

Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Springfield
10.0 out of 10, Exceptional, (58 reviews)
"Great property"
United States
Lynn
The price is CA $308
CA $354 total
includes taxes & fees
Jun 7 - Jun 8
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

Charming Downtown Stay | Victorian Beauty & Modern Comfort

Charming Downtown Stay | Victorian Beauty & Modern Comfort
Springfield
9.6 out of 10, Exceptional, (22 reviews)
"It was very nice. Very friendly host. Location was perfect. "
United States
Dianne H.
The price is CA $295
CA $340 total
includes taxes & fees
Jun 7 - Jun 8
Charming Downtown Stay | Victorian Beauty & Modern Comfort

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Springfield
9.8 out of 10, Exceptional, (6 reviews)
"Our third year visiting the Bressner House and everything was again perfect "
United States
Diane
The price is CA $583
CA $1,292 total
includes taxes & fees
May 20 - May 21
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

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

Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance
Springfield
8.0 out of 10, Very good, (5 reviews)
"Plenty of room for a large group!"
United States
Amy V.
The price is CA $822
CA $947 total
includes taxes & fees
Jun 7 - Jun 8
Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance

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

Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
Springfield
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful house and charming details throughout the two floors. Easy access to the downtown sites. Really nice stay!"
United States
Mark J.
The price is CA $496
CA $572 total
includes taxes & fees
Jun 1 - Jun 2
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Find out more about Middletown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Middletown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 Lincoln Speedway, Lincoln's New Salem State Historic Site, and Camp Butler National Cemetery. 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.