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Middletown Vacation Rentals

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Check prices for these dates

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

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 SAR 552
SAR 851 total
includes taxes & fees
23 Aug - 24 Aug
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 SAR 571
SAR 920 total
includes taxes & fees
31 Aug - 1 Sep
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, (2 reviews)
"It was super clean, very nicely decorated, and a perfect space for our family of 5. The host is very friendly and communicative."
United States
Hayley P.
The price is SAR 593
SAR 1,710 total
includes taxes & fees
9 Sep - 10 Sep
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 SAR 496
SAR 1,055 total
includes taxes & fees
24 Aug - 25 Aug
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 SAR 595
SAR 675 total
includes taxes & fees
25 Aug - 26 Aug
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 SAR 745
SAR 841 total
includes taxes & fees
25 Aug - 26 Aug
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 SAR 767
SAR 882 total
includes taxes & fees
25 Aug - 26 Aug
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 SAR 595
SAR 675 total
includes taxes & fees
25 Aug - 26 Aug
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 SAR 749
SAR 841 total
includes taxes & fees
26 Aug - 27 Aug
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, (24 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 SAR 767
SAR 882 total
includes taxes & fees
24 Aug - 25 Aug
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 SAR 1,979
SAR 2,278 total
includes taxes & fees
25 Aug - 26 Aug
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 SAR 3,567
SAR 4,974 total
includes taxes & fees
24 Aug - 25 Aug
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 SAR 1,198
SAR 1,381 total
includes taxes & fees
24 Aug - 25 Aug
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 SAR 1,774
SAR 3,746 total
includes taxes & fees
7 Sep - 8 Sep
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
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

Inn at 835 Boutique Hotel

Inn at 835 Boutique Hotel

10/10 Excellent
"Beautiful room, friendly staff, delicious breakfast. I don’t have cause to travel to Springfield often, but if I do, I will definitely consider staying here again."
Adam J. 1-night trip
Posted 2 hours ago
Inn at 835 Boutique Hotel

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.