Middletown, IL Holiday Rentals

Middletown Holiday Homes

Apartment

Lincoln’s Loft - Speakeasy Suite

10.0

Exceptional

(48 Reviews)

2 Bedrooms 1 Bath 6 Guests 1300 ft²

US $206/Night 7 Nights - US $1,439

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House

Livin on The Wedge

1 Bedroom 3 Baths 8 Guests 1205.56 ft²

US $270/Night 7 Nights - US $1,890

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Days Inn by Wyndham Lincoln, IL/Route 66

Highly Rated

Hotel

Days Inn by Wyndham Lincoln, IL/Route 66

9.0

Exceptional

(73 Reviews)

1 Bath

US $64/Night 7 Nights - US $448

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Apartment

Lincoln’s Loft - Hawthorne Suite Downtown Lincoln, IL

10.0

Exceptional

(28 Reviews)

3 Bedrooms 1 Bath 8 Guests

US $206/Night 7 Nights - US $1,439

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Other

Leah Bungalow

1 Bedroom 1 Bath 5 Guests

US $60/Night 7 Nights - US $420

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Hotel

Hampton Inn by Hilton Lincoln

8.8

Fabulous

(638 Reviews)

1 Bath

US $92/Night 7 Nights - US $643

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Price Dropped

House

Wednesday’s Lair - Lincoln, Il

10.0

Exceptional

(11 Reviews)

2 Bedrooms 2 Baths 6 Guests 1500 ft²

US $224/Night 7 Nights - US $1,565

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Hotel

Days Inn by Wyndham Lincoln, IL Route 66

9.5

Exceptional

(31 Reviews)

4 Baths

US $378/Night 7 Nights - US $2,648

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Hotel

Comfort Inn & Suites near Route 66

8.0

Excellent

(536 Reviews)

1 Bath

US $76/Night 7 Nights - US $534

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Apartment

Safe, No Cleaning Fee, Fully Furnished Detached Garage Guesthouse

10.0

Exceptional

(5 Reviews)

1 Bedroom 1 Bath 4 Guests

US $154/Night 7 Nights - US $1,076

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Hotel

Hampton By Hilton Lincoln

7.7

Very Good

(61 Reviews)

1 Bath

US $120/Night 7 Nights - US $843

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Price Dropped

Hotel

Edn Hotel Lincoln

7.4

Very Good

(31 Reviews)

1 Bath

US $71/Night 7 Nights - US $495

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More Top-Rated Holiday Homes in Middletown Area

Why Choose Rent By Owner for your Middletown Holiday Homes?

What makes our Holiday Homes special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Middletown

How to Book Your Middletown Holiday Homes

What's our booking process?

Our platform allows you to browse a curated selection of holiday homes. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

Search Properties

Use our filters to find the right property that fits your needs.

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Middletown

More Top-Rated Holiday Homes in Middletown Area

Common Holiday Homes Amenities

What amenities can you expect?

Our Holiday Homes are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

Fully-equipped kitchens with modern appliances
Comfortable living areas with flat-screen TVs
Free Wi-Fi for staying connected
Air conditioning and heating for year-round comfort
In-unit washers and dryers for convenience
Luxurious bedrooms with premium bedding
Spa-like bathrooms with soaking tubs or walk-in showers

Middletown Holiday Homes Frequently Asked Questions

1. How many Holiday Homes are available in Middletown?

Currently, the total number of properties listed by RBO in 2026 is over 24 in the Middletown area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Middletown. 