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Middletown Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
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 holiday rentals

A spacious living area with a staircase, leather sofas, and a chandelier.

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 HK$1,153
HK$1,778 total
includes taxes & fees
23 Aug - 24 Aug
Lincoln’s Loft - Speakeasy Suite
A living room with a brown leather couch, a cityscape pillow, a kitchen with modern appliances, and a loft area above.

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 HK$1,193
HK$1,920 total
includes taxes & fees
30 Aug - 31 Aug
Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
A modern kitchen with a large island, pendant lights, and a black and white color scheme.

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 HK$1,239
HK$3,571 total
includes taxes & fees
23 Aug - 24 Aug
Top-Rated Premier Modern Getaway
A modern kitchen with white cabinets, a dining area with blue chairs, and a small trash bin.

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 HK$1,035
HK$2,202 total
includes taxes & fees
24 Aug - 25 Aug
Tranquil 3-bedroom house with a massage chair
A grand staircase with ornate woodwork and a large mirror.

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 HK$1,243
HK$1,409 total
includes taxes & fees
25 Aug - 26 Aug
Historic Luxury Stay | Downtown Springfield | Step-Free Access
A large, historic brick building with a turret and multiple windows, surrounded by a well-maintained lawn and a metal fence.

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 HK$1,557
HK$1,757 total
includes taxes & fees
25 Aug - 26 Aug
Spacious Carriage House | Private Entrance | Historic & Stylish
A large, historic brick building with a prominent tower and arched windows, surrounded by well-maintained lawns and trees.

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 HK$1,601
HK$1,842 total
includes taxes & fees
25 Aug - 26 Aug
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
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.

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 HK$1,243
HK$1,409 total
includes taxes & fees
25 Aug - 26 Aug
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort
A large, historic brick building with a prominent tower and arched windows, surrounded by well-maintained lawns and trees.

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 HK$1,564
HK$1,755 total
includes taxes & fees
26 Aug - 27 Aug
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
A large, two-story brick house with a prominent corner turret and multiple windows.

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 HK$1,602
HK$1,843 total
includes taxes & fees
24 Aug - 25 Aug
Charming Downtown Stay | Victorian Beauty & Modern Comfort
A grand staircase with ornate woodwork and a large mirror.

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 HK$4,134
HK$4,758 total
includes taxes & fees
25 Aug - 26 Aug
Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance
A spa room with a wooden hot tub, a glass partition, and a painting on the wall.

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 HK$7,448
HK$10,387 total
includes taxes & fees
24 Aug - 25 Aug
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
A spacious bedroom with a large bed, a television, and a view of the outdoors.

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 HK$2,503
HK$2,885 total
includes taxes & fees
24 Aug - 25 Aug
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
A large, two-story brick house with a prominent corner turret and multiple windows.

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 HK$3,705
HK$7,822 total
includes taxes & fees
7 Sept - 8 Sept
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

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

Travelodge by Wyndham Atlanta, Illinois

Travelodge by Wyndham Atlanta, Illinois

10/10 Excellent
"Last minute booking, decent place to stay."
Richard 1-night trip
Posted 8 hours ago
Travelodge by Wyndham Atlanta, Illinois

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:

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

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Middletown has to offer?

Modern Bungalow Home with Mid-Century Flair: This holiday home rental outside of Middletown offers a garden, a BBQ 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 that 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 wider area, you’ll find Illinois State Fairgrounds and Lincoln's Tomb.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.