Middletown Holiday Rentals

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Holiday Rentals in Middletown

COZY BUNGALO

9.4 out of 10, Exceptional, (70)
"Clean, well stocked. Close to fair. "
COZY BUNGALO

Modern Bungalow Home with Mid-Century Flair

8.6 out of 10, Excellent, (40)
"Tasteful and relaxed. Enjoyed our stay and visit with family in Springfield."
The price is NZ$365
includes taxes & fees
6 Oct - 7 Oct
Modern Bungalow Home with Mid-Century Flair

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

2.0 star property
9.8 out of 10, Exceptional, (21)
"Host was easy to work with and property was nice! "
The price is NZ$364
includes taxes & fees
8 Oct - 9 Oct
Tranquil 2-bedroom house with a massage chair and a multi-purpose 3rd room

Adorable house

7.4 out of 10, Good, (8)
"The host provided everything that we could possibly need! Very nice, clean, and updated home in a nice neighborhood. We were very happy with our stay!"
Adorable house

Lovely 2-Bedroom Unit in Springfield

9.8 out of 10, Exceptional, (21)
"Great location, close to the capital, shopping, dining and historical sites. The property is well kept and comfortable for a stay in Springfield."
Lovely 2-Bedroom Unit in Springfield

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

10.0 out of 10, Exceptional, (50)
"Great hosts and accommodations!"
The price is NZ$505
includes taxes & fees
29 Oct - 30 Oct
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

New remodel three bedroom house in pleasant Springfield

7.0 out of 10, Good, (15)
"Nice little house, convenient to fairgrounds. Upstairs front bedroom was a little warm. Vent fully open but not a lot of cold air flowing through. Bed in that bedroom was low, no problem for me but I could see it might be difficult for some. It was comfortable. Other bedrooms nice."
The price is NZ$423
includes taxes & fees
6 Oct - 7 Oct
New remodel three bedroom house in pleasant Springfield

Lincoln’s Loft - Speakeasy Suite

10.0 out of 10, Exceptional, (45)
"This is our second stay at this property.We love the location.This is a fun place to stay,we love the speakeasy theme "
The price is NZ$353
includes taxes & fees
9 Oct - 10 Oct
Lincoln’s Loft - Speakeasy Suite

Charming Springfield Home: 2 Mi to Downtown

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!"
Charming Springfield Home: 2 Mi to Downtown

The Loft on the Square

10.0 out of 10, Exceptional, (83)
"This place was amazing, lots of amenities and the town of Petersburg is very charming. "
The Loft on the Square

Beautiful Country Setting with Heated Inground Pool and Stocked Pond

10.0 out of 10, Exceptional, (97)
"Family stay with all the kids and grandkids. Just quality family time. "
Beautiful Country Setting with Heated Inground Pool and Stocked Pond

Historic Bungalow: For Groups & Families Sleeps 11

9.2 out of 10, Wonderful, (11)
"Lots of room for my multi-generational family of 7! Our host was super-responsive and helpful."
Historic Bungalow: For Groups & Families Sleeps 11

Property is not available

6.0 out of 10, (1)
The price is NZ$309
includes taxes & fees
6 Oct - 7 Oct
Property is not available

Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

2.0 star property
10.0 out of 10, Exceptional, (6)
"Everything was really nice and as described. Would stay there again!"
The price is NZ$336
includes taxes & fees
19 Oct - 20 Oct
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

Western Barn

9.6 out of 10, Exceptional, (8)
"As advertised."
Western Barn

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

10.0 out of 10, Exceptional, (25)
"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."
Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

10.0 out of 10, Exceptional, (2)
"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."
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

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

10.0 out of 10, Exceptional, (15)
"Perfect spot for our stay"
Pet friendly remodeled bungalow home just two blocks from Washington Park.

Wednesday’s Lair - Lincoln, Il

10.0 out of 10, Exceptional, (11)
"Lincoln has some great local shops and cafes. This house is conveniently located and has wonderful decor. "
The price is NZ$563
includes taxes & fees
3 Nov - 4 Nov
Wednesday’s Lair - Lincoln, Il

Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood

10.0 out of 10, Exceptional, (3)
"Nice property very happy with our stay"
Whitt’s End -- a spacious private lodging in a historic Springfield 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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Top Middletown Hotel Reviews

Find out more about Middletown

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Middletown holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as NZ$309 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday 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 holiday.

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 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?

COZY BUNGALO: This holiday home rental outside of Middletown is located in the city centre, and has a patio, a garden and a BBQ 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 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.