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Holiday Rentals in Montgomery County
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Our top choices for Montgomery County holiday rentals
Holiday Home in Litchfield
Edwards House; Litchfield, IL; Pets welcome10.0 out of 10, Exceptional, (21)
"Perfect place to stop on road trip to Arkansas. Had everything I needed. "
Jon L.
The price is €147
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Home in Litchfield
Route 66 house; Litchfield IL; Pets welcome9.8 out of 10, Exceptional, (19)
"Nice little place, check in and communication excellent. Perfect for us when visiting my Dad who lives near by."
Mike O.
The price is €147
includes taxes & fees
2 Jan - 3 Jan 2026
Holiday Home in Litchfield
Harrison House; Litchfield, IL; Pets welcome10.0 out of 10, Exceptional, (16)
"Cozy house, great amenities, and the hosts responded to questions quickly. Definitely will be staying again!"
Jennifer G.
The price is €151
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Home in Litchfield
Jackson House; Pets Welcome10.0 out of 10, Exceptional, (20)
"The home was clean, in a central location of Litchfield, spacious, and we appreciated that the host allowed pets! would recommend this VRBO to anyone visiting the Litchfield area."
Shelby B.
The price is €157
includes taxes & fees
19 Jan - 20 Jan 2026
Holiday Home in Litchfield
State Street House; 3-br house; PETS WELCOME; Litchfield10.0 out of 10, Exceptional, (14)
"Great location. Wonderful owner"
David E.
The price is €194
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Home in Raymond
The Relaxing House - Quiet 2 Bedroom HomeThe price is €170
includes taxes & fees
5 Jan - 6 Jan 2026
10.0 out of 10, Exceptional, (5)
"This was our second time staying here and it didn't dissapoint. "
Kimberly D.
The price is €370
includes taxes & fees
15 Jan - 16 Jan 2026
Apartment in Vandalia
Unique apartment in historic downtown10.0 out of 10, Exceptional, (18)
"My colleague and I were attending a fundraiser and this was perfect for our short stay!"
Leah W.
The price is €118
includes taxes & fees
28 Jan - 29 Jan 2026
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 Montgomery County Hotel Reviews
Quality Inn and Suites Springfield Southwest near I-72
10/10 Excellent
Find out more about Montgomery County
Holiday Homes in Montgomery County
Search for holiday homes in Montgomery County on Expedia.ie! You can easily find your home rentals, villas, holiday apartments in Montgomery County using one of the methods below:
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Look no further and take a look at our great range of rental properties in Montgomery County!