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Top Holiday Rentals in Middletown

Lovely 2-Bedroom Unit in Springfield

10.0 out of 10, Exceptional, (16)
"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, (49)
"Great hosts and accommodations!"
The price is £191
includes taxes & fees
20 Aug - 21 Aug
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

Beautiful Country Setting with Heated Inground Pool and Stocked Pond

10.0 out of 10, Exceptional, (97)
"Great place, pond and fishing was great. Big pool, nice hot tub with many things to do. We will rent again. Thanks"
Beautiful Country Setting with Heated Inground Pool and Stocked Pond

Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

10.0 out of 10, Exceptional, (24)
"Tons of character, wonderfully taken care of, great hosts, Aubrey is super easy to work with and very accommodating. Loved the flexibility to host our wedding in a unique way that fit us!"
Three Pines Petersburg - Luxurious 10 Bedroom Home in Historic Petersburg

Modern Bungalow Home with Mid-Century Flair

9.0 out of 10, Wonderful, (34)
"Great location. Close to downtown, restaurants, and the state fair and pet friendly too."
The price is £188
includes taxes & fees
17 Aug - 18 Aug
Modern Bungalow Home with Mid-Century Flair

New remodel three bedroom house in pleasant Springfield

7.4 out of 10, Good, (11)
"Clean placeLet us grill outsideSpacious and comfy for what we needed"
The price is £201
includes taxes & fees
14 Aug - 15 Aug
New remodel three bedroom house in pleasant Springfield

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."
The price is £768
includes taxes & fees
17 Aug - 18 Aug
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

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

Wednesday’s Lair - Lincoln, Il

10.0 out of 10, Exceptional, (9)
"Lincoln has some great local shops and cafes. This house is conveniently located and has wonderful decor. "
The price is £250
includes taxes & fees
19 Aug - 20 Aug
Wednesday’s Lair - Lincoln, Il

Cozy retreat

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"
Cozy retreat

The Cozy Suite near all Attractions in downtown

8.8 out of 10, Excellent, (5)
"Really great apartment close to so many things. Easy to get to. Very clean. Awesome neighborhood. "
The Cozy Suite near all Attractions in downtown

Very Cozy and Secluded. Completely remodeled beautiful back apartment

10.0 out of 10, Exceptional, (56)
"This would be a great place for an extended stay! Great people and the place was very comfortable!"
The price is £110
includes taxes & fees
18 Aug - 19 Aug
Very Cozy and Secluded. Completely remodeled beautiful back apartment

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!"
The price is £165
includes taxes & fees
14 Aug - 15 Aug
Charming Springfield Home: 2 Mi to Downtown

Lincoln’s Loft - Speakeasy Suite

10.0 out of 10, Exceptional, (43)
"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 £169
includes taxes & fees
28 Aug - 29 Aug
Lincoln’s Loft - Speakeasy Suite

Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks

2.0 star property
10.0 out of 10, Exceptional, (2)
"5 senior ladies on a girl trip and we couldn't have picked a better place to stay, everything was PERFECT. The home was beautiful and sooo comfortable, the location was just right. Would absolutely stay there again."
The price is £278
includes taxes & fees
7 Sept - 8 Sept
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Everything was really nice and as described. Would stay there again!"
The price is £149
includes taxes & fees
19 Aug - 20 Aug
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

Western Barn

9.6 out of 10, Exceptional, (7)
"As advertised."
Western Barn

Capital Suite on 6th Street - King Bed / Downtown!

9.2 out of 10, Wonderful, (9)
"It was great! We loved everything about it and the owners instructions were well said and clear making the check in and check out process very easy"
The price is £129
includes taxes & fees
18 Aug - 19 Aug
Capital Suite on 6th Street - King Bed / Downtown!

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

10.0 out of 10, Exceptional, (2)
"Great place to stay ! The home was clean, cozy, and had everything you could need from the multiple charging cubes to bathroom and kitchen essentials. If you appreciate antique furnishings this home has it. The backyard was nice and had cute pathways between the many trees and garden. Our dog loved all the smells too ! The host is quick to respond and easy going. Highly recommend ! "
Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood

Blue Room at the Feitshans House

10.0 out of 10, Exceptional, (1)
"The Blue Room at the Feitshans House was beautiful, elegant and very accomodating for our weekend stay in Springfield. It is centrally located to all the downtown historic activities and eateries are just a short drive in all directions. The home is tastefully decorated and has all the amenities one needs for a short or long term stay. We enjoyed the historical books and antiques throughout the home. It was easy to get in and out and parking is more than adequate. We had a wonderful stay in the...
The price is £129
includes taxes & fees
19 Aug - 20 Aug
Blue Room at the Feitshans House
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

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?

Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm: This holiday home rental outside of Middletown is located in the city centre, and has a fireplace, a garden and air conditioning to put you at ease 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. Make the most of books 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.