Middletown Vacation Rentals

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Vacation Rentals in Middletown

Lovely 2-Bedroom Unit in Springfield

10.0 out of 10, Exceptional, (15)
"Property owner is very responsive. The apartment is complete. You basically need to bring yourself and enjoy the stay."
Lovely 2-Bedroom Unit in Springfield

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

10.0 out of 10, Exceptional, (47)
"Great hosts and accommodations!"
The price is CA $301
CA $333 total
includes taxes & fees
Sep 2 - Sep 3
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

8.8 out of 10, Excellent, (33)
"Great location. Close to downtown, restaurants, and the state fair and pet friendly too."
The price is CA $174
CA $334 total
includes taxes & fees
Aug 10 - Aug 11
Modern Bungalow Home with Mid-Century Flair

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 CA $241
CA $453 total
includes taxes & fees
Aug 13 - Aug 14
Wednesday’s Lair - Lincoln, Il

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 CA $149
CA $342 total
includes taxes & fees
Aug 14 - Aug 15
New remodel three bedroom house in pleasant Springfield

Modern Like New LUXURY 3,200 SQ FT Home In An Awesome Location! Sleeps 12!

9.8 out of 10, Exceptional, (101)
"Wayne was a great host and his property is in a great location and neighborhood. Would definitely look to stay again if we’re back in the area!"
Modern Like New LUXURY 3,200 SQ FT Home In An Awesome Location! Sleeps 12!

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 CA $118
CA $198 total
includes taxes & fees
Aug 18 - Aug 19
Very Cozy and Secluded. Completely remodeled beautiful back apartment

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 CA $972
CA $1,702 total
includes taxes & fees
Aug 14 - Aug 15
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

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 CA $205
CA $305 total
includes taxes & fees
Aug 28 - Aug 29
Lincoln’s Loft - Speakeasy Suite

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 CA $242
CA $273 total
includes taxes & fees
Aug 20 - Aug 21
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

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 CA $465
CA $535 total
includes taxes & fees
Aug 19 - Aug 20
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks

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)
"Very good value for a basic apartment in a good location."
The price is CA $116
CA $232 total
includes taxes & fees
Sep 1 - Sep 2
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, (1)
"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

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 CA $105
CA $306 total
includes taxes & fees
Aug 14 - Aug 15
Charming Springfield Home: 2 Mi to Downtown
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 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?

Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm: Visitors like this Middletown vacation home rental. It is located in the city center 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 you can cook with friends or family. Make the most of the 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 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.