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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Middletown vacation rentals

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1. Lincoln’s Loft - Speakeasy Suite

Lincoln’s Loft - Speakeasy Suite
Lincoln
10.0 out of 10, Exceptional, (56 reviews)
"Stand outs: host, shower pressure, cleanliness, decor. Would stay again!"
United States
Kim C.
The price is ￥23,435
￥36,155 total
includes taxes & fees
Aug 23 - Aug 24
Lincoln’s Loft - Speakeasy Suite
Interior

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

Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
Lincoln
10.0 out of 10, Exceptional, (29 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 ￥24,272
￥39,084 total
includes taxes & fees
Aug 30 - Aug 31
Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
Interior

3. Top-Rated Premier Modern Getaway

Top-Rated Premier Modern Getaway
Petersburg
10.0 out of 10, Exceptional, (1 review)
"property has been renovated inside. Pictures accurately depict the property which was a great place to stay for our trip."
United States
Jared D.
The price is ￥25,188
￥72,601 total
includes taxes & fees
Sep 1 - Sep 2
Top-Rated Premier Modern Getaway
Coffee/tea maker, fridge, microwave, oven

4. Tranquil 3-bedroom house with a massage chair

Tranquil 3-bedroom house with a massage chair
Springfield
9.8 out of 10, Exceptional, (23 reviews)
"Host was easy to work with and property was nice! "
United States
Nicole W.
The price is ￥21,073
￥44,826 total
includes taxes & fees
Aug 24 - Aug 25
Tranquil 3-bedroom house with a massage chair
Interior

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

Historic Luxury Stay | Downtown Springfield | Step-Free Access
Springfield
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay ! Close to all things Lincoln. "
United States
Patricia J.
The price is ￥25,301
￥28,684 total
includes taxes & fees
Aug 24 - Aug 25
Historic Luxury Stay | Downtown Springfield | Step-Free Access
Exterior

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

Spacious Carriage House | Private Entrance | Historic & Stylish
Springfield
9.8 out of 10, Exceptional, (45 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 ￥31,653
￥35,709 total
includes taxes & fees
Aug 24 - Aug 25
Spacious Carriage House | Private Entrance | Historic & Stylish
Exterior

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

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Springfield
9.4 out of 10, Exceptional, (28 reviews)
"Beautiful property and a great location!"
United States
Rebecca k.
The price is ￥32,589
￥37,493 total
includes taxes & fees
Aug 24 - Aug 25
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Exterior

8. 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, (18 reviews)
"Very nice and a very comfortable stay"
United States
Camille L.
The price is ￥25,301
￥28,684 total
includes taxes & fees
Aug 24 - Aug 25
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort
Exterior

9. 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, (62 reviews)
"Exceptional historic property. Hosts were very responsive, prompt, extremely helpful. Lovely home was perfect for our stay. Excellent location, great parking, close to sites on our to-do list. Hoping we can return soon. Highly recommend!"
United States
Valerie S.
The price is ￥31,986
￥36,721 total
includes taxes & fees
Aug 26 - Aug 27
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Exterior

10. Charming Downtown Stay | Victorian Beauty & Modern Comfort

Charming Downtown Stay | Victorian Beauty & Modern Comfort
Springfield
9.6 out of 10, Exceptional, (23 reviews)
"We loved the home and had a wonderful time. I would suggest that the kitchen would be a bit better stocked. (no coffee filters, no salt & pepper)I would also suggest the staff checks the light bulbs periodically for being burned out (we had several) "
United States
Claudia G.
The price is ￥32,557
￥37,456 total
includes taxes & fees
Aug 24 - Aug 25
Charming Downtown Stay | Victorian Beauty & Modern Comfort
Interior

11. 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 ￥84,115
￥96,800 total
includes taxes & fees
Aug 25 - Aug 26
Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance
Interior

12. 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)
"Hosted our second bachelor here and it’s still one of the coolest places we’ve ever stayed! George is an awesome host!"
United States
Tyler B.
The price is ￥151,449
￥211,192 total
includes taxes & fees
Aug 25 - Aug 26
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
4 bedrooms, iron/ironing board, WiFi (free), bed sheets

13. 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)
"We rented the 2nd and 3rd floors and were very pleased with the place. It definitely had the historic charm, was very clean, and very close to all of the historical attractions. Would definitely recommend. "
United States
Chelsea T.
The price is ￥50,920
￥58,700 total
includes taxes & fees
Aug 25 - Aug 26
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
Exterior

14. 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, (8 reviews)
"Great home for large family gatherings."
United States
Eric H.
The price is ￥75,326
￥159,049 total
includes taxes & fees
Sep 7 - Sep 8
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Coffee/tea maker, fridge, microwave, oven

15. Charming 2-bedroom house with AC in Springfield

Charming 2-bedroom house with AC in Springfield
Springfield
The price is ￥28,724
￥47,184 total
includes taxes & fees
Aug 20 - Aug 21
Charming 2-bedroom house with AC in Springfield
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

President Abraham Lincoln Springfield - DoubleTree by Hilton

President Abraham Lincoln Springfield - DoubleTree by Hilton

10/10 Excellent
"Staff, especially Kyle at front desk amazing. Hilton Honors never worked, never updated my password, was basically a no go."
Nancy 3-night trip
Posted 16 hours ago
President Abraham Lincoln Springfield - DoubleTree by Hilton

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 Lincoln Speedway, Rail Golf Course, 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.