Middletown Vacation Rentals

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Our top choices for Middletown vacation rentals

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 ¥10,998
¥39,148 total
includes taxes & fees
Mar 29 - Mar 30
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, (49 reviews)
"Property was clean, pet friendly, good location, ample room, easily accessible, coffee available overall nice place would rent again "
United States
Michele N.
The price is ¥15,233
¥33,574 total
includes taxes & fees
Mar 29 - Mar 30
Modern Bungalow Home with Mid-Century Flair

Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL

Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
Lincoln
10.0 out of 10, Exceptional, (28 reviews)
"This property is perfect for our family, allowing us all to stay in the same place and relax!"
United States
Sean W.
The price is ¥20,657
¥33,886 total
includes taxes & fees
Mar 31 - Apr 1
Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL

Lincoln’s Loft - Speakeasy Suite

Lincoln’s Loft - Speakeasy Suite
Lincoln
10.0 out of 10, Exceptional, (54 reviews)
"Very interesting place. Extremely nice and comfortable. Quaint and friendly little community!"
United States
Diane R.
The price is ¥21,396
¥32,999 total
includes taxes & fees
Mar 29 - Mar 30
Lincoln’s Loft - Speakeasy Suite

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 ¥27,893
¥57,602 total
includes taxes & fees
Apr 7 - Apr 8
Wednesday’s Lair - Lincoln, Il

Safe, No Cleaning Fee, Fully Furnished Detached Garage Guesthouse

Safe, No Cleaning Fee, Fully Furnished Detached Garage Guesthouse
Lincoln
10.0 out of 10, Exceptional, (4 reviews)
"Really enjoyed it. Couldwalk downtown. Very pet friendly. Had everything we needed!"
United States
Janice B.
The price is ¥19,924
¥24,495 total
includes taxes & fees
Mar 30 - Mar 31
Safe, No Cleaning Fee, Fully Furnished Detached Garage Guesthouse

Historic Luxury Stay | Downtown Springfield | Step-Free Access

Historic Luxury Stay | Downtown Springfield | Step-Free Access
Springfield
10.0 out of 10, Exceptional, (8 reviews)
"Great place to stay ! Close to all things Lincoln. "
United States
Patricia J.
The price is ¥27,739
¥31,632 total
includes taxes & fees
Mar 31 - Apr 1
Historic Luxury Stay | Downtown Springfield | Step-Free Access

one-bedroom apartment 1,500 square feet of inviting comfort and practical style.

one-bedroom apartment 1,500 square feet of inviting comfort and practical style.
Springfield
8.0 out of 10, Very Good, (1 review)
"The apartment was clean, we enjoyed our stay. It was in the right location for what we wanted to do."
United States
Karla P.
The price is ¥11,656
¥23,353 total
includes taxes & fees
Mar 30 - Mar 31
one-bedroom apartment 1,500 square feet of inviting comfort and practical style.

Spacious Carriage House | Private Entrance | Historic & Stylish

Spacious Carriage House | Private Entrance | Historic & Stylish
Springfield
10.0 out of 10, Exceptional, (43 reviews)
"A very spacious lodging that was very clean and very comfortable. Will stay here again when in Springfield."
United States
Christine
The price is ¥35,855
¥39,403 total
includes taxes & fees
Apr 20 - Apr 21
Spacious Carriage House | Private Entrance | Historic & Stylish

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Springfield
9.8 out of 10, Exceptional, (18 reviews)
"Had a wonderful time with friends and family it was a very lovely place "
United States
Ava A.
The price is ¥37,422
¥42,320 total
includes taxes & fees
Apr 6 - Apr 7
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

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, (12 reviews)
"Great stay, everything was clean and plenty of space. "
United States
Lindsay S.
The price is ¥27,691
¥31,577 total
includes taxes & fees
Mar 31 - Apr 1
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

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
9.0 out of 10, Wonderful, (8 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 ¥151,421
¥211,152 total
includes taxes & fees
Mar 28 - Mar 29
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!

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, (56 reviews)
"Great property"
United States
Lynn
The price is ¥36,616
¥40,509 total
includes taxes & fees
Apr 27 - Apr 28
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, (21 reviews)
"This home is absolutely gorgeous. "
United States
Pamela B.
The price is ¥35,681
¥40,410 total
includes taxes & fees
Apr 13 - Apr 14
Charming Downtown Stay | Victorian Beauty & Modern Comfort

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)
"Amazing 1 night stay. Everything we needed. "
United States
Charles G.
The price is ¥90,350
¥104,032 total
includes taxes & fees
Mar 29 - Mar 30
Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Springfield
9.6 out of 10, Exceptional, (5 reviews)
"Our third year visiting the Bressner House and everything was again perfect "
United States
Diane
The price is ¥80,667
¥157,993 total
includes taxes & fees
Apr 6 - Apr 7
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

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, (6 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 ¥63,467
¥73,113 total
includes taxes & fees
Apr 27 - Apr 28
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.
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Top Middletown Hotel Reviews

Find out more about Middletown

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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.