Holiday Rentals in Montgomery County

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Featured Holiday Rentals in Montgomery County

Jackson House; Pets Welcome
Fridge, microwave, oven, stovetop

Jackson House; Pets Welcome

10.0 out of 10, Exceptional, (15)
"Overflow holiday guests stayed at this cute, clean, comfortable home. A wonderful experience with exceptionally kind, engaged, owners! "
The price is €157
includes taxes & fees
30 Sept - 1 Oct
Jackson House; Pets Welcome
Route 66 house; Litchfield IL; Pets welcome
Fridge, microwave, oven, stovetop

Route 66 house; Litchfield IL; Pets welcome

10.0 out of 10, Exceptional, (16)
"Cute little place we were visiting our grandchildren who live in the area and we all had a great time the house is well decorated so cute and everything you need is there. We will check to see if this place is available every time we visit the grandchildren."
The price is €147
includes taxes & fees
28 Sept - 29 Sept
Route 66 house; Litchfield IL; Pets welcome
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks
Exterior

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

9.6 out of 10, Exceptional, (13)
"Very relaxing fun place to stay!"
The price is €343
includes taxes & fees
28 Sept - 29 Sept
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks
State Street House; 3-br house; PETS WELCOME; Litchfield
Private kitchen

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

9.8 out of 10, Exceptional, (10)
"Great house with a really great layout. Great location for accessing the parts of Litchfield we wanted to find. Super responsive host. "
The price is €193
includes taxes & fees
28 Sept - 29 Sept
State Street House; 3-br house; PETS WELCOME; Litchfield
Private country setting with large indoor pool
A heated pool

Private country setting with large indoor pool

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"
Private country setting with large indoor pool
Edwards House; Litchfield, IL; Pets welcome
1 bedroom, iron/ironing board, WiFi, bed sheets

Edwards House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (21)
"Mike and Amy have a beautiful cozy place to stay. My partner and I had a wonderful time and were super comfy during our stay!"
The price is €147
includes taxes & fees
1 Oct - 2 Oct
Edwards House; Litchfield, IL; Pets welcome
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving
Smart TV, fireplace, table football

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

10.0 out of 10, Exceptional, (3)
"This was our second time staying here and it didn't dissapoint. "
The price is €343
includes taxes & fees
29 Sept - 30 Sept
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving
Harrison House; Litchfield, IL; Pets welcome
Property grounds

Harrison House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (13)
"Everything was in excellent shape and the fenced yard was great for the pups."
The price is €161
includes taxes & fees
28 Sept - 29 Sept
Harrison House; Litchfield, IL; Pets welcome
Charming Springfield Stunner: a relaxing escape in peaceful Jerome Village
Fridge, microwave, oven, stovetop

Charming Springfield Stunner: a relaxing escape in peaceful Jerome Village

10.0 out of 10, Exceptional, (3)
"Love this place. "
Charming Springfield Stunner: a relaxing escape in peaceful Jerome Village
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Exterior

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

10.0 out of 10, Exceptional, (28)
"Beautiful property. Couldn’t be better. "
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds
Property grounds

Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds

9.6 out of 10, Exceptional, (4)
"Stayed here before...always nice "
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
Exterior

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

9.6 out of 10, Exceptional, (25)
"This cabin is so snug and comfortable. It is expertly decorated and furnished so that you only need to bring a change of clothes and you’re set. It was good vibes only. "
The price is €162
includes taxes & fees
26 Sept - 27 Sept
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
Craftsman styled home in the heart of downtown Highland
Fridge, microwave, oven, stovetop

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (63)
"We had a wonderful stay! Plenty of room and Jennifer did a fantastic job of communicating with us! "
Craftsman styled home in the heart of downtown Highland
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood
5 bedrooms, iron/ironing board, WiFi, bed sheets

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

8.6 out of 10, Excellent, (4)
"The house was very clean "
The price is €547
includes taxes & fees
22 Oct - 23 Oct
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood
The Carlinville Cottage
Fridge, microwave, oven, stovetop

The Carlinville Cottage

10.0 out of 10, Exceptional, (13)
"This was a fantastic stay in a wonderfully clean space! We really enjoyed Carlinville cottage ans would stay again!"
The price is €441
includes taxes & fees
29 Sept - 30 Sept
The Carlinville Cottage
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Exterior

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

10.0 out of 10, Exceptional, (50)
"Great hosts and accommodations!"
The price is €219
includes taxes & fees
28 Sept - 29 Sept
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Beach-themed rental with many activities within walking distance.
Microwave

Beach-themed rental with many activities within walking distance.

10.0 out of 10, Exceptional, (2)
"Very Clean and comfortable!"
The price is €184
includes taxes & fees
26 Oct - 27 Oct
Beach-themed rental with many activities within walking distance.
Capital Suite on 6th Street - King Bed / Downtown!
Fridge, microwave, oven, stovetop

Capital Suite on 6th Street - King Bed / Downtown!

8.4 out of 10, Very good, (11)
"It was great! We loved everything about it and the owners instructions were well said and clear making the check in and check out process very easy"
The price is €147
includes taxes & fees
28 Sept - 29 Sept
Capital Suite on 6th Street - King Bed / Downtown!
Home is on the original 1926-1930 Route 66 alignment
Terrace/patio

Home is on the original 1926-1930 Route 66 alignment

10.0 out of 10, Exceptional, (90)
"Great Stay with family a couple of blocks away"
The price is €149
includes taxes & fees
30 Sept - 1 Oct
Home is on the original 1926-1930 Route 66 alignment
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
4 bedrooms, iron/ironing board, free WiFi, bed sheets

Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks

2.0 star property
10.0 out of 10, Exceptional, (3)
"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."
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Montgomery County Hotel Reviews

Route 66 Hotel, Springfield, Illinois

Route 66 Hotel, Springfield, Illinois

10/10 Excellent
"Was a great stay. Rooms were beautiful. However the tub water smelled like dog water and had tiny hair in it. The curtain also appeared to had spots of dryed blood on it. Overall was a great 5 star stay and would stay again."
Siera 1-night trip
Posted 3 days ago
Route 66 Hotel, Springfield, Illinois

Find out more about Montgomery County

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: 

  • View our selection of featured holiday homes in Montgomery County
  • Use the map to find apartments and other holiday rentals in the Montgomery County neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday homes in Montgomery County while they last

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