Holiday Rentals in Middletown

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Holiday Rentals in Middletown

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

9.8 out of 10, Exceptional, (20)
"To stay in such a beautifully restored historic mansion was a real treat, and such a fun way to get our whole family together to celebrate a milestone birthday. The house has a lot of space to gather together, but with several individual parlors, it also made it easy to visit or play games in smaller groups. The kitchen is a good size and well stocked for preparing meals, and having 2 ovens, sinks, and dishwashers was helpful. The owners have created a very comfortable guest house with lovely...
Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

Modern Bungalow Home with Mid-Century Flair

9.0 out of 10, Wonderful, (25)
"We had a nice stay. The kitchen appliances were in great condition but there were NO extras. We would have had to buy all spices, oils, even baking trays etc.. if we wanted to cook there. That is my only complaint, as we like to save money and not have to eat out. The kitchen would have been lovely to use if there were just some basic supplies and cookware. Otherwise, the stay was nice the house was clean and we appreciated the use of a house instead of having to get a hotel room for our...
The price is €215
includes taxes & fees
19 Feb - 20 Feb
Modern Bungalow Home with Mid-Century Flair

Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

10.0 out of 10, Exceptional, (36)
"Our family had a great time going through family photos on the smart TV and celebrating with a birthday cake and dinner on the second floor!"
The price is €237
includes taxes & fees
23 Feb - 24 Feb
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

Historic Luxury Stay | Downtown Springfield | Step-Free Access

2.0 star property
10.0 out of 10, Exceptional, (4)
"Extremely well set up for a nice stay and had a wonderful kitchen and very comfy beds. Just minutes from the Lincoln home, museum and library. Hosts were very helpful by letting us rent an additional night. We only rented the first floor and were very happy. It is a beautiful house that is now a bit of a holdover on that part of 6th Street."
The price is €187
includes taxes & fees
22 Feb - 23 Feb
Historic Luxury Stay | Downtown Springfield | Step-Free Access

Charming 2-bedroom house with WiFi, AC in awesome Springfield

The price is €260
includes taxes & fees
19 Feb - 20 Feb
Charming 2-bedroom house with WiFi, AC in awesome Springfield

Pet friendly remodeled bungalow home just two blocks from Washington Park.

10.0 out of 10, Exceptional, (5)
"Perfect spot for our stay"
Pet friendly remodeled bungalow home just two blocks from Washington Park.

Lincoln’s Loft - Speakeasy Suite

10.0 out of 10, Exceptional, (37)
"If you are traveling to Lincoln, IL for any reason, I would highly recommend staying at the Lincoln Lofts. They are a hidden gem in downtown Lincoln right off the town square. The units are immaculate, thoughtfully decorated, and stocked with everything you will need and more for your stay. Megan was a wonderful host and very responsive. My family and I will definitely be back!"
The price is €225
includes taxes & fees
19 Mar - 20 Mar
Lincoln’s Loft - Speakeasy Suite

New remodel three bedroom house in pleasant Springfield

2.0 out of 10, (1)
"I paid for this house and the host messaged me and offered me the other house they had for the same price. When we got to the house it was only 55 degrees and took 8 hours for the living room to be comfortable. We didnt even stay in the rooms because it was so cold. There was a used bar of soap and razor top cover in the bath. One of the rooms didnt have a door knob there was toilet paper in the hole. The vent in the kitchen had dust and cob webs all in it. There was hair on the decorations. A...
The price is €269
includes taxes & fees
22 Feb - 23 Feb
New remodel three bedroom house in pleasant Springfield

Charming Springfield Home: 2 Mi to Downtown

10.0 out of 10, Exceptional, (8)
"Found this home while looking for somewhere to stay as we travelled to the Springfield area for a wedding. Couldn't have asked for a better fit for us. The home was just as advertised and shown in the photos. The home was very clean and had all the amenities we've come to expect during our travels. Communication concerning check-in and check-out instructions was great with no surprises. Would definitely recommend if you are in need of accommodations in the Springfield area. "
Charming Springfield Home: 2 Mi to Downtown

Historic Bungalow: For Groups & Families Sleeps 11

9.0 out of 10, Wonderful, (4)
"Was a wonderful property felt right at home host kept in contact to make sure everything was good would definitely stay here again "
Historic Bungalow: For Groups & Families Sleeps 11

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

9.2 out of 10, Wonderful, (5)
"This historical landmark is beautifully preserved. It was well appointed and super comfortable. The beds were incredible. We enjoyed our stay!"
The price is €240
includes taxes & fees
23 Feb - 24 Feb
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room

2.0 star property
10.0 out of 10, Exceptional, (4)
"I have nothing negative to say about our stay at Regina’s duplex! The bonus room on the basement was a great feature. The linens were top tier and plentiful. Regina was so thoughtful about asking what kind of snacks our kids like so she could leave some for them! She was so communicative! I am very grateful we got to experience this trip and stay! "
The price is €210
includes taxes & fees
19 Feb - 20 Feb
Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room

Beautiful Country Setting with Heated Inground Pool and Stocked Pond

10.0 out of 10, Exceptional, (96)
"This house and property is amazing, and the pictures do not do it justice. It’s beautiful on its own, however we also had the bonus of having it decorated for Christmas. Lori not only had a Christmas tree, but there were multiple other decorations hidden in corners of each room, several animated animals like Mickey Mouse that my grandkids loved, and there was even an Elf on a Shelf. The owners not only had everything we needed in a well stocked kitchen, coffee, spices, plenty of towels and...
Beautiful Country Setting with Heated Inground Pool and Stocked Pond

Spacious Carriage House | Private Entrance | Historic & Stylish

9.8 out of 10, Exceptional, (37)
"A very spacious lodging that was very clean and very comfortable. Will stay here again when in Springfield."
The price is €233
includes taxes & fees
19 Feb - 20 Feb
Spacious Carriage House | Private Entrance | Historic & Stylish

The Loft on the Square

9.8 out of 10, Exceptional, (80)
"This place was amazing, lots of amenities and the town of Petersburg is very charming. "
The Loft on the Square

Holly & Matt Suite @ Three Pines Petersburg

10.0 out of 10, Exceptional, (20)
"Beautiful place to stay. Aubrey was an excellent host."
Holly & Matt Suite @ Three Pines Petersburg

Hideaway in the Eaves | Historic Charm & Modern Comfort | Walkable Location

2.0 star property
10.0 out of 10, Exceptional, (1)
"A very nice property we really enjoyed our stay. "
The price is €187
includes taxes & fees
20 Feb - 21 Feb
Hideaway in the Eaves | Historic Charm & Modern Comfort | Walkable Location

The Pasfield House - Historic Mansion: The Nest

10.0 out of 10, Exceptional, (1)
"We were in town for my daughter’s senior pictures. We enjoyed our stay so much. Happy we chose to stay here instead of a hotel. We even took some of her photos on the beautiful front porch!"
The price is €180
includes taxes & fees
19 Feb - 20 Feb
The Pasfield House - Historic Mansion: The Nest

Historical Mid Century Modern Home Designed By Robert Lloyd Buckles

2.0 star property
10.0 out of 10, Exceptional, (1)
"My family and I truly enjoyed our stay. The historical townhouse was spacious and afforded us space to spread out but also spaces to gather. We loved the period details and appliances. The one drawback was the train noise at various hours, but the noise didn’t ruin our sleep. The access to Idle Hour and Guest House was particularly enjoyable. We would all gladly stay here again!"
Historical Mid Century Modern Home Designed By Robert Lloyd Buckles

The Conkling House in the Old Aristocracy Hill Neighborhood

7.6 out of 10, Good, (5)
"The house was beautiful, absolutely gorgeous. If you like historic properties, you will love this place. Our issue, however, was the bathroom situation. The house has 1 teeny-tiny shower and 3 powder rooms. The listing should better reflect that. shojld "
The price is €844
includes taxes & fees
23 Feb - 24 Feb
The Conkling House in the Old Aristocracy Hill Neighborhood
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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Other types of properties in Middletown you may be interested in

State House Inn

3.0 star property
6.8 out of 10, (1035)
"Location "
The price is €113
includes taxes & fees
1 Mar - 2 Mar
State House Inn

President Abraham Lincoln Springfield - DoubleTree by Hilton

4.0 star property
8.2 out of 10, Very good, (1000)
"excellent experience, staff was very pleasant to work with "
The price is €132
includes taxes & fees
2 Mar - 3 Mar
President Abraham Lincoln Springfield - DoubleTree by Hilton

Carpenter Street Hotel

2.5 star property
8.6 out of 10, Excellent, (1003)
"Brief stay but everything was good. Friendly staff, good parking situation. The breakfast was very good. No sign of recycling. Room was very clean, and plenty of hot water, would stay there again but bring your own pillow."
The price is €97
includes taxes & fees
24 Feb - 25 Feb
Carpenter Street Hotel
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.

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?

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg: This holiday home rental outside of Middletown offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

What’s there to see and do in Middletown?

While exploring the area, visit the sights like Lincoln Speedway, Lincoln's New Salem State Historic Site and Camp Butler National Cemetery. 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.