Photo by Wesley Blackwell

Holiday Rentals in Montgomery County

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Our top choices for Montgomery County holiday rentals

10.0 out of 10, Exceptional, (21)
"Perfect place to stop on road trip to Arkansas. Had everything I needed. "
United States
Jon L.
The price is €147
includes taxes & fees
3 Jan - 4 Jan 2026
Edwards House; Litchfield, IL; Pets welcome
9.8 out of 10, Exceptional, (19)
"Nice little place, check in and communication excellent. Perfect for us when visiting my Dad who lives near by."
United States
Mike O.
The price is €147
includes taxes & fees
2 Jan - 3 Jan 2026
Route 66 house; Litchfield IL; Pets welcome
10.0 out of 10, Exceptional, (16)
"Cozy house, great amenities, and the hosts responded to questions quickly. Definitely will be staying again!"
United States
Jennifer G.
The price is €151
includes taxes & fees
3 Jan - 4 Jan 2026
Harrison House; Litchfield, IL; Pets welcome

Holiday Home in Litchfield

Jackson House; Pets Welcome
10.0 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."
United States
Shelby B.
The price is €157
includes taxes & fees
19 Jan - 20 Jan 2026
Jackson House; Pets Welcome
10.0 out of 10, Exceptional, (14)
"Great location. Wonderful owner"
United States
David E.
The price is €194
includes taxes & fees
1 Jan - 2 Jan 2026
State Street House; 3-br house; PETS WELCOME; Litchfield
The price is €170
includes taxes & fees
5 Jan - 6 Jan 2026
The Relaxing House - Quiet 2 Bedroom Home
10.0 out of 10, Exceptional, (5)
"This was our second time staying here and it didn't dissapoint. "
United States
Kimberly D.
The price is €370
includes taxes & fees
15 Jan - 16 Jan 2026
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving
10.0 out of 10, Exceptional, (18)
"My colleague and I were attending a fundraiser and this was perfect for our short stay!"
United States
Leah W.
The price is €118
includes taxes & fees
28 Jan - 29 Jan 2026
Unique apartment in historic downtown
10.0 out of 10, Exceptional, (2)
"Very Clean and comfortable!"
United States
Cade W.
The price is €173
includes taxes & fees
30 Dec - 31 Dec
Beach-themed rental with many activities within walking distance.
9.6 out of 10, Exceptional, (28)
"Great little cabin to relax in while on the road :)"
United States
Ashlee S.
The price is €178
includes taxes & fees
31 Dec - 1 Jan 2026
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
10.0 out of 10, Exceptional, (23)
"Clean, quaint, and conveniently located. Perfect for a weekend retreat!"
United States
Curtis T.
The price is €119
includes taxes & fees
4 Jan - 5 Jan 2026
Unique loft in historic downtown
10.0 out of 10, Exceptional, (97)
"We love staying in this house. This is our 3rd stay and it never disappoints! Perfect location in town close to our favorite ice cream shop. Highly recommend. "
United States
Cindy T.
The price is €150
includes taxes & fees
3 Jan - 4 Jan 2026
Home is on the original 1926-1930 Route 66 alignment
10.0 out of 10, Exceptional, (14)
"Very comfortable, cozy, and quaint decor. Lovely gardens. Made to feel welcome by host."
United States
Rayma P.
The price is €109
includes taxes & fees
30 Dec - 31 Dec
Cozy studio located in small town America, Bunker Hill, IL.
10.0 out of 10, Exceptional, (8)
"Great place to stay ! Close to all things Lincoln. "
United States
Patricia J.
The price is €170
includes taxes & fees
30 Dec - 31 Dec
Historic Luxury Stay | Downtown Springfield | Step-Free Access
9.8 out of 10, Exceptional, (19)
"Perfect spot for our stay"
United States
Caleb H.
Pet friendly remodeled bungalow home just two blocks from Washington Park.
10.0 out of 10, Exceptional, (41)
"A very spacious lodging that was very clean and very comfortable. Will stay here again when in Springfield."
United States
Christine
The price is €215
includes taxes & fees
31 Dec - 1 Jan 2026
Spacious Carriage House | Private Entrance | Historic & Stylish

Apartment in Carlinville

Light Filled Loft on Town Square
2.0 star property
10.0 out of 10, Exceptional, (2)
"The loft was amazing as well as the views looking out to the town square!"
United States
Gerry G.
The price is €214
includes taxes & fees
2 Jan - 3 Jan 2026
Light Filled Loft on Town Square
10.0 out of 10, Exceptional, (52)
"The home was beautifully restored and it was a perfect place for our family to get her for an event in Springfield. Located close to many historical sites."
United States
A. L.
The price is €210
includes taxes & fees
25 Jan - 26 Jan 2026
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

Holiday Home in Carlinville

The Carlinville Cottage
10.0 out of 10, Exceptional, (17)
"Our stay was perfect and convenient. We will definitely be back. Thank you!"
United States
Gary D.
The price is €437
includes taxes & fees
30 Dec - 31 Dec
The Carlinville Cottage
9.0 out of 10, Wonderful, (8)
"George is an awesome host! Our group of high schoolers love this place! Plenty to keep them busy and engaged!"
United States
Ann P.
The price is €332
includes taxes & fees
1 Jan - 2 Jan 2026
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
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

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Holiday Homes in Montgomery County

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Look no further and take a look at our great range of rental properties in Montgomery County!