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Montgomery County Holiday Rentals

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Featured Montgomery County Holiday Rentals

Microwave, oven, stovetop
The Relaxing House - Quiet 2 Bedroom Home

The Relaxing House - Quiet 2 Bedroom Home

Raymond
The price is HK$973
HK$1,526 total
includes taxes & fees
10 Dec - 11 Dec
The Relaxing House - Quiet 2 Bedroom Home
Fridge, microwave, oven, stovetop
Jackson House; Pets Welcome

Jackson House; Pets Welcome

Litchfield
10.0 out of 10, Exceptional, (17)
"Good communication, easy process, quiet neighborhood, comfortable house and an overall good value."
United States
Terry R.
The price is HK$895
HK$1,403 total
includes taxes & fees
8 Dec - 9 Dec
Jackson House; Pets Welcome
Property grounds
Harrison House; Litchfield, IL; Pets welcome

Harrison House; Litchfield, IL; Pets welcome

Litchfield
10.0 out of 10, Exceptional, (15)
"Cozy house, great amenities, and the hosts responded to questions quickly. Definitely will be staying again!"
United States
Jennifer G.
The price is HK$926
HK$1,444 total
includes taxes & fees
3 Jan - 4 Jan 2026
Harrison House; Litchfield, IL; Pets welcome
Fridge, microwave, oven, stovetop
Route 66 house; Litchfield IL; Pets welcome

Route 66 house; Litchfield IL; Pets welcome

Litchfield
9.8 out of 10, Exceptional, (18)
"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 HK$810
HK$1,312 total
includes taxes & fees
14 Dec - 15 Dec
Route 66 house; Litchfield IL; Pets welcome
A heated pool
Private country setting with large indoor pool

Private country setting with large indoor pool

Virden
9.4 out of 10, Exceptional, (16)
"It’s nothing fancy but a great place for families to get a way with things to do right in the building"
United States
Drew W.
Private country setting with large indoor pool
1 bedroom, iron/ironing board, WiFi, bed sheets
Edwards House; Litchfield, IL; Pets welcome

Edwards House; Litchfield, IL; Pets welcome

Litchfield
10.0 out of 10, Exceptional, (21)
"Nice stay as our stopover point between Texas and Northern Wisconsin."
United States
Robert N.
The price is HK$810
HK$1,312 total
includes taxes & fees
12 Dec - 13 Dec
Edwards House; Litchfield, IL; Pets welcome
Private kitchen
State Street House; 3-br house; PETS WELCOME; Litchfield

State Street House; 3-br house; PETS WELCOME; Litchfield

Litchfield
10.0 out of 10, Exceptional, (13)
"Great location. Wonderful owner"
United States
David E.
The price is HK$1,082
HK$1,724 total
includes taxes & fees
1 Jan - 2 Jan 2026
State Street House; 3-br house; PETS WELCOME; Litchfield
Smart TV, fireplace
Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield

Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield

Litchfield
10.0 out of 10, Exceptional, (2)
"Very clean and beds were extremely comfortable. Very nice space"
United States
Catherine M.
Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield
Exterior
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks

Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks

Irving
9.6 out of 10, Exceptional, (14)
"The BEST time ever! 2 years running! Love the property!"
United States
Ben H.
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks
Smart TV, fireplace, table football
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving

New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving

Irving
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 HK$1,752
HK$3,069 total
includes taxes & fees
11 Dec - 12 Dec
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving
Exterior
Home < 3 Mi to Rte 66 & Lake Lou Yaeger!

Home < 3 Mi to Rte 66 & Lake Lou Yaeger!

Litchfield
Home < 3 Mi to Rte 66 & Lake Lou Yaeger!
Iron/ironing board, free WiFi, bed sheets
Light Filled Loft on Town Square

Light Filled Loft on Town Square

2.0 star property
Carlinville
The price is HK$1,183
HK$1,906 total
includes taxes & fees
8 Dec - 9 Dec
Light Filled Loft on Town Square
View from property
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Springfield
9.8 out of 10, Exceptional, (14)
"Beautiful property with everything we needed for a perfect stay. Very spacious!"
United States
Amy E.
The price is HK$1,743
HK$1,998 total
includes taxes & fees
8 Dec - 9 Dec
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Outdoor dining
Pet friendly remodeled bungalow home just two blocks from Washington Park.

Pet friendly remodeled bungalow home just two blocks from Washington Park.

Springfield
9.8 out of 10, Exceptional, (18)
"Perfect spot for our stay"
United States
Caleb H.
Pet friendly remodeled bungalow home just two blocks from Washington Park.
5 bedrooms, iron/ironing board, WiFi, bed sheets
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood

Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood

Springfield
8.8 out of 10, Excellent, (5)
"The house was very clean "
United States
Lance C.
The price is HK$2,175
HK$4,046 total
includes taxes & fees
14 Dec - 15 Dec
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood
Exterior
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!

Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!

Mulberry Grove
9.6 out of 10, Exceptional, (28)
"Perfect place for shinrin-yoku (forest bathing)!"
United States
Lori M.
The price is HK$842
HK$1,627 total
includes taxes & fees
22 Dec - 23 Dec
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
Terrace/patio
Grand Victorian Carlinville home on Rt. 66.

Grand Victorian Carlinville home on Rt. 66.

Carlinville
10.0 out of 10, Exceptional, (11)
"We will stay there again if we're in the area."
United States
Scott C.
Grand Victorian Carlinville home on Rt. 66.
Exterior
Charming Downtown Stay | Victorian Beauty & Modern Comfort

Charming Downtown Stay | Victorian Beauty & Modern Comfort

Springfield
9.6 out of 10, Exceptional, (21)
"This home is absolutely gorgeous. "
United States
Pamela B.
The price is HK$1,743
HK$1,998 total
includes taxes & fees
8 Dec - 9 Dec
Charming Downtown Stay | Victorian Beauty & Modern Comfort
Exterior
Spacious Carriage House | Private Entrance | Historic & Stylish

Spacious Carriage House | Private Entrance | Historic & Stylish

Springfield
10.0 out of 10, Exceptional, (41)
"Great location, walking distance to most locations. Enjoyed having the space the house provided. Check in and out was smooth, everything was as described. Staying in a historic house like this is a cool thing to do."
United States
Anthony P.
The price is HK$1,692
HK$1,939 total
includes taxes & fees
8 Dec - 9 Dec
Spacious Carriage House | Private Entrance | Historic & Stylish
Terrace/patio
Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment

Girard
10.0 out of 10, Exceptional, (96)
"The historic house was perfect for our vacation. "
United States
Kelly F.
The price is HK$561
HK$1,337 total
includes taxes & fees
8 Dec - 9 Dec
Home is on the original 1926-1930 Route 66 alignment
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

Quality Inn and Suites Springfield Southwest near I-72

10/10 Excellent
"Very well located "
Jose and Nereida 1-night trip
Posted 4 days ago
Quality Inn and Suites Springfield Southwest near I-72