Middletown Vacation Rentals

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Dec 19 - Dec 21
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Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Middletown

Fridge, microwave, oven, stovetop
Modern Bungalow Home with Mid-Century Flair

Vacation Home in Springfield

8.4 out of 10, Very Good, (44)
"It worked out perfect for our family hoping to use it again soon"
United States
Stephanie R.
$204 nightly
The price is $216
Dec 7 - Dec 8
Total with taxes and fees
Modern Bungalow Home with Mid-Century Flair
Fridge, microwave, oven, stovetop
COZY BUNGALO

Vacation Home in Springfield

9.4 out of 10, Exceptional, (75)
"Nice and area is close to where we were visiting "
United States
Kelly O.
COZY BUNGALO
View from property
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Vacation Home in Springfield

9.8 out of 10, Exceptional, (14)
"Beautiful property with everything we needed for a perfect stay. Very spacious!"
United States
Amy E.
$253 nightly
The price is $255
Dec 7 - Dec 8
Total with taxes and fees
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Interior
Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

Vacation Home in Petersburg

10.0 out of 10, Exceptional, (27)
"Three Pines was a perfect venue for our needs. Very clean and charming. Aubrey was very accommodating, flexible, & quick to respond to all my questions."
United States
Carrie N.
Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg
Fridge, microwave, oven, stovetop
Lovely 2-Bedroom Unit in Springfriend

Apartment in Downtown Springfield

8.8 out of 10, Excellent, (22)
"Would stay again. Stairs! Underground parking- have to pay. Our trucks would not fit but street parking seemed good and close (no charge). "
United States
Stacy
Lovely 2-Bedroom Unit in Springfriend
Outdoor dining
Pet friendly remodeled bungalow home just two blocks from Washington Park.

Vacation Home in Springfield

9.8 out of 10, Exceptional, (18)
"Perfect spot for our stay"
United States
Caleb H.
Pet friendly remodeled bungalow home just two blocks from Washington Park.
Fridge, microwave, oven, stovetop
Spacious & Cozy ~ Mins to Downtown

Vacation Home in Springfield

8.4 out of 10, Very Good, (16)
"It was wonderful. Hopefully, we can get it next year."
United States
Beverly F.
Spacious & Cozy ~ Mins to Downtown
Fridge, microwave, oven, stovetop
Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room

Vacation Home in Springfield

2.0 star property
9.8 out of 10, Exceptional, (21)
"Great service, very clean, good location and has everything you need."
United States
Colleen R.
$215 nightly
The price is $228
Dec 7 - Dec 8
Total with taxes and fees
Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room
Exterior
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

Vacation Home in Springfield

10.0 out of 10, Exceptional, (52)
"The home was beautifully restored and it was a perfect place for our family to get her for an event in Springfield. Located close to many historical sites."
United States
A. L.
$246 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Exterior
Charming Downtown Stay | Victorian Beauty & Modern Comfort

Vacation Home in Springfield

9.6 out of 10, Exceptional, (21)
"This home is absolutely gorgeous. "
United States
Pamela B.
$253 nightly
The price is $255
Dec 7 - Dec 8
Total with taxes and fees
Charming Downtown Stay | Victorian Beauty & Modern Comfort
Exterior
Spacious Carriage House | Private Entrance | Historic & Stylish

Vacation Home in Springfield

10.0 out of 10, Exceptional, (41)
"Great location, walking distance to most locations. Enjoyed having the space the house provided. Check in and out was smooth, everything was as described. Staying in a historic house like this is a cool thing to do."
United States
Anthony P.
$245 nightly
The price is $247
Dec 7 - Dec 8
Total with taxes and fees
Spacious Carriage House | Private Entrance | Historic & Stylish
Exterior
Charming 2-bedroom apartment in Springfield with AC

Apartment in Springfield

2.0 star property
10.0 out of 10, Exceptional, (3)
"Very nice worked great for my needs"
United States
Dennis S.
Charming 2-bedroom apartment in Springfield with AC
Fridge, microwave, oven, stovetop
Lovely 2-Bedroom Unit in Springfield

Apartment in Downtown Springfield

9.4 out of 10, Exceptional, (30)
"Great location, close to the capital, shopping, dining and historical sites. The property is well kept and comfortable for a stay in Springfield."
United States
scott
Lovely 2-Bedroom Unit in Springfield
Dining
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

Vacation Home in Springfield

9.4 out of 10, Exceptional, (3)
"Amazing property. Couldn’t have asked for anything better. Kitchen, living room, laundry and dining room on every floor. Luxurious bedrooms. A beautiful old mansion. In the heart of Springfield. Every amenity you could imagine. We had an amazingly wonderful weekend of sharing and church family time."
United States
Carol C.
$999 nightly
The price is $1,006
Dec 15 - Dec 16
Total with taxes and fees
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Dining
Holly & Matt Suite @ Three Pines Petersburg

Cottage in Petersburg

10.0 out of 10, Exceptional, (23)
"The additional space worked great for our guests.Very clean, comfortable, and charming."
United States
Carrie N.
Holly & Matt Suite @ Three Pines Petersburg
House (2 Bedrooms) | Interior
Charming Springfield Home: 2 Mi to Downtown

Cottage in Springfield

3.0 star property
10.0 out of 10, Exceptional, (2)
"The cottage was nicely renovated and decorated. It had a good supply of necessities and very comfortable!"
United States
Amie
Charming Springfield Home: 2 Mi to Downtown
Fridge, microwave, oven, stovetop
Beautiful Country Setting with Heated Inground Pool and Stocked Pond

Vacation Home in Dawson

10.0 out of 10, Exceptional, (98)
"Family stay with all the kids and grandkids. Just quality family time. "
United States
Michael H.
Beautiful Country Setting with Heated Inground Pool and Stocked Pond
Fridge, microwave, oven, stovetop
Cozy retreat

Apartment in Springfield

10.0 out of 10, Exceptional, (1)
"The outcome was better than photos. Didn't spend much time their throughout the afternoon but over all experience was great. Really appreciated the extra condiments and kitchen items I didn't have to go out and buy extra things. Easy and fast contact response"
United States
Toni C.
Cozy retreat
Property grounds
Property is not available

Cabin in Petersburg

6.0 out of 10, (1)
$171 nightly
The price is $181
Dec 6 - Dec 7
Total with taxes and fees
Property is not available
Fridge, microwave, oven, stovetop
Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL

Apartment in Lincoln

10.0 out of 10, Exceptional, (26)
"This property is perfect for our family, allowing us all to stay in the same place and relax!"
United States
Sean W.
$199 nightly
The price is $211
Dec 8 - Dec 9
Total with taxes and fees
Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL
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

Comfort Suites near Route 66

Comfort Suites near Route 66

10/10 Excellent
"Room was clean and spacious. Beds were comfortable and the breakfast was wonderful. I always stay here when I visit."
Ronniece 2-night trip
Posted 2 days ago
Comfort Suites near 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 $181 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.

Explore a world of travel with Expedia

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?

COZY BUNGALO: Visitors like this Middletown vacation home rental. It is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Middletown?

While exploring the area, visit the sights like 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.