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Middletown Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Middletown vacation rentals

A cozy interior with a staircase, leather sofas, a chandelier, and bookshelves filled with books and decorative items.

1. Lincoln’s Loft - Speakeasy Suite

Lincoln’s Loft - Speakeasy Suite
Lincoln
10.0 out of 10, Exceptional, (57 reviews)
"Great place to stay!"
United States
Kyle O.
$245 nightly
The price is $260
Nov 5 - Nov 6
Total with taxes and fees
Lincoln’s Loft - Speakeasy Suite
A living room with a brown leather sofa, a city-themed pillow, a kitchen with modern appliances, and a loft-style ceiling.

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

Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
Lincoln
10.0 out of 10, Exceptional, (33 reviews)
"This property is perfect for our family, allowing us all to stay in the same place and relax!"
United States
Sean W.
$228 nightly
The price is $242
Oct 19 - Oct 20
Total with taxes and fees
Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
A carpeted staircase with a handrail, a door with a number plate, and a light fixture on the ceiling.

3. "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
10.0 out of 10, Exceptional, (1 review)
"The place was very clean and spacious. It is decorated Mid Century Modern. 2nd floor is the main floor.We loved the 3rd floor media room where many channels were available to watch/stream. Paddington Bear was watching atop his suit case. There is a half bath on 3rd floor if the need arises while watching shows.The bathrooms were cute. I meant to take pictures. The master bedrooms bathroom had a blue tub and cute pattern wall paper.We slept well.We were in town for our grandson's soccer...
United States
Carol S.
$348 nightly
The price is $369
Oct 21 - Oct 22
Total with taxes and fees
"Living on the Wedge" A 3-bedroom house in Lincoln on Historic Route 66.
A modern kitchen with a large island, pendant lights, and a black and white color scheme.

4. Top-Rated Premier Modern Getaway

Top-Rated Premier Modern Getaway
Petersburg
10.0 out of 10, Exceptional, (3 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.
$452 nightly
The price is $497
Oct 19 - Oct 20
Total with taxes and fees
Top-Rated Premier Modern Getaway
A kitchen with wooden cabinets, a dining area with a table and chairs, and a television in the background.

5. Modern Bungalow Home with Mid-Century Flair

Modern Bungalow Home with Mid-Century Flair
Springfield
8.2 out of 10, Very good, (74 reviews)
"Nice place"
United States
Diane
$199 nightly
The price is $211
Oct 19 - Oct 20
Total with taxes and fees
Modern Bungalow Home with Mid-Century Flair
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.

6. 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, (20 reviews)
"It was a very nicely located and clean property large enough for a family to stay in as they visit the sites in Springfield."
United States
Joseph
$182 nightly
The price is $184
Oct 21 - Oct 22
Total with taxes and fees
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.

7. 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, (65 reviews)
"The Rowland Suite was perfect for our stay in Springfield!"
United States
Robert S.
$227 nightly
The price is $228
Oct 21 - Oct 22
Total with taxes and fees
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
A large, historic brick building with a turret and multiple windows, surrounded by a well-maintained lawn and a metal fence.

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

Spacious Carriage House | Private Entrance | Historic & Stylish
Springfield
9.8 out of 10, Exceptional, (46 reviews)
"A very spacious lodging that was very clean and very comfortable. Will stay here again when in Springfield."
United States
Christine
$226 nightly
The price is $227
Oct 21 - Oct 22
Total with taxes and fees
Spacious Carriage House | Private Entrance | Historic & Stylish
A grand staircase with ornate woodwork and a large mirror.

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

Historic Luxury Stay | Downtown Springfield | Step-Free Access
Springfield
10.0 out of 10, Exceptional, (17 reviews)
"Great place to stay ! Close to all things Lincoln. "
United States
Patricia J.
$182 nightly
The price is $184
Oct 21 - Oct 22
Total with taxes and fees
Historic Luxury Stay | Downtown Springfield | Step-Free Access
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, (25 reviews)
"It was very nice. Very friendly host. Location was perfect. "
United States
Dianne H.
$244 nightly
The price is $246
Oct 27 - Oct 28
Total with taxes and fees
Charming Downtown Stay | Victorian Beauty & Modern Comfort
A large, historic brick building with a prominent tower and arched windows, surrounded by well-maintained lawns and trees.

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

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Springfield
9.4 out of 10, Exceptional, (31 reviews)
"Beautiful property and a great location!"
United States
Rebecca k.
$232 nightly
The price is $234
Oct 21 - Oct 22
Total with taxes and fees
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
A spacious bedroom with a large bed, a television, and a view of the outdoors.

12. 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, (8 reviews)
"Beautiful house and charming details throughout the two floors. Easy access to the downtown sites. Really nice stay!"
United States
Mark J.
$363 nightly
The price is $366
Oct 19 - Oct 20
Total with taxes and fees
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
A spa room with a wooden hot tub, a glass partition, and a painting on the wall.

13. 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.
$1,250 nightly
The price is $1,325
Oct 19 - Oct 20
Total with taxes and fees
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
A grand staircase with ornate woodwork and a large mirror.

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

Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance
Springfield
8.4 out of 10, Very good, (6 reviews)
"Plenty of room for a large group!"
United States
Amy V.
$602 nightly
The price is $607
Oct 25 - Oct 26
Total with taxes and fees
Grand Historic Retreat | Walk to Capitol & Attractions | Timeless Elegance
A large, two-story brick house with a prominent corner turret and multiple windows.

15. 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.
$990 nightly
The price is $998
Oct 28 - Oct 29
Total with taxes and fees
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Private kitchen

16. The coolest most fun house with pool hot tub pool table air hockey and much more

The coolest most fun house with pool hot tub pool table air hockey and much more
Springfield
$477 nightly
The price is $506
Oct 21 - Oct 22
Total with taxes and fees
The coolest most fun house with pool hot tub pool table air hockey and much more
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

Days Inn by Wyndham Lincoln, IL/Route 66

Days Inn by Wyndham Lincoln, IL/Route 66

8/10 Good
"Overall it is a great value for the price. Shower curtain needed to be replaced and refrigerator froze everything even when set on 1. Otherwise, very comfortable bed and quiet area of town. Staff were friendly and helpful."
Cary 2-night trip
Posted 1 hour ago
Days Inn by Wyndham Lincoln, IL/Route 66

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $24 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.