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Find Vacation Homes in Montgomery County, IL from $169

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Vacation Homes in Montgomery County

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

Springfield
9.4 out of 10, Exceptional, (3)
"Amazing property. Couldn’t have asked for anything better. Kitchen, living room, laundry and dining room on every floor. Luxurious bedrooms. A beautiful old mansion. In the heart of Springfield. Every amenity you could imagine. We had an amazingly wonderful weekend of sharing and church family time."
United States
Carol C.
$999 nightly
The price is $1,006
Dec 15 - Dec 16
Total with taxes and fees
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

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.
$490 nightly
The price is $520
Dec 10 - Dec 11
Total with taxes and fees
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood

The Relaxing House - Quiet 2 Bedroom Home

Raymond
$185 nightly
The price is $196
Dec 10 - Dec 11
Total with taxes and fees
The Relaxing House - Quiet 2 Bedroom Home

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.
$209 nightly
The price is $222
Jan 1 - Jan 2, 2026
Total with taxes and fees
State Street House; 3-br house; PETS WELCOME; Litchfield

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.
$159 nightly
The price is $169
Dec 14 - Dec 15
Total with taxes and fees
Route 66 house; Litchfield IL; Pets welcome

Charming Downtown Stay | Victorian Beauty & Modern Comfort

Springfield
9.6 out of 10, Exceptional, (21)
"This home is absolutely gorgeous. "
United States
Pamela B.
$255 nightly
The price is $257
Dec 8 - Dec 9
Total with taxes and fees
Charming Downtown Stay | Victorian Beauty & Modern Comfort

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.
$162 nightly
The price is $172
Dec 8 - Dec 9
Total with taxes and fees
Home is on the original 1926-1930 Route 66 alignment

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.
$247 nightly
The price is $249
Dec 8 - Dec 9
Total with taxes and fees
Spacious Carriage House | Private Entrance | Historic & Stylish

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.
$255 nightly
The price is $257
Dec 8 - Dec 9
Total with taxes and fees
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Plainview Vineyard Retreat by StayLage

2.0 star property
Shipman
10.0 out of 10, Exceptional, (1)
"Quiet place to relax after a long day. Clean and will rent again if given the choice. "
United States
Christopher B.
Plainview Vineyard Retreat by StayLage

Sunflower Cottage

Springfield
10.0 out of 10, Exceptional, (3)
"Clean home and worked out well for our trip "
United States
Caleb H.
Sunflower Cottage

Family Friendly Home Centrally Located with Private Yard

Springfield
10.0 out of 10, Exceptional, (11)
"This is a cute home in a very convenient location. The owners were very responsive. "
United States
Julie H.
Family Friendly Home Centrally Located with Private Yard

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.

Rainbow Retreat ~ 3-bedroom fun loving home full of color!

Springfield
9.8 out of 10, Exceptional, (6)
"Great location. Wonderful home. Lots of neighborhood roads to walk the dog on. "
United States
Linda F.
Rainbow Retreat ~ 3-bedroom fun loving home full of color!

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

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.
$170 nightly
The price is $180
Dec 8 - Dec 9
Total with taxes and fees
Jackson House; 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.
$159 nightly
The price is $169
Dec 12 - Dec 13
Total with taxes and fees
Edwards House; Litchfield, IL; Pets welcome

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

Springfield
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.
$248 nightly
The price is $250
Dec 8 - Dec 9
Total with taxes and fees
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

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.

Craftsman styled home in the heart of downtown Highland

Highland
10.0 out of 10, Exceptional, (68)
"Great place! We enjoyed the proximity to downtown. Visiting for a family wedding we all fit nicely in the house. We will rent again for our next family gathering. "
United States
Sharon B.
Craftsman styled home in the heart of downtown Highland
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

Find out more about Montgomery County

Booking Tips to Find the Best Montgomery County Vacation Homes


How much does it cost to rent a vacation home in Montgomery County?

You can find incredible Montgomery County vacation homes for all types of budgets: between $169 and $1,006 per night. The more amenities the rental has, and its proximity to popular places, the higher the price.


What is the best time to stay in a vacation home in Montgomery County?

If you are looking for a great deal on your vacation home in Montgomery County, consider visiting in , when prices are usually cheaper.


How many vacation homes are available for rent in Montgomery County?

There are 51 rental houses to choose from for your trip. You’ll find holiday homes located throughout the city, near sightseeing spots, and close to local nature areas.


How do I find the best deal for a vacation home in Montgomery County?

Begin by entering your trip dates to see what type of Montgomery County rental houses are available. Use the map to zoom closer into the areas or zoom out to include more locations. Use the filters on the left side of your search results to narrow down by star rating, price, number of bedrooms, amenities, and more—Expedia makes it easy to score the best deal for your budget.


Why should I rent a vacation home in Montgomery County?

Booking Montgomery County vacation home rentals is the perfect way to spend a vacation because of the privacy, variety of amenities, and comfort you’ll have in your own space.


What amenities are available in a private vacation home?

When thinking about what you want in your Montgomery County rental house, dream big! Depending on your budget and the area, you’ll find amenities like a private pool, hot tub, free parking, fully-equipped kitchen, in-home washer and dryer, Wi-Fi, and a beautiful view or easy access to local sightseeing spots. You can even filter your search results by accessibility to ensure that everyone in your party will be comfortable.


Why should I book a vacation home with Expedia?

Expedia has some of the best selection and deals on available vacation homes in the area—and all in one place. We reward you with members points back on every booking and ensure you get the right accommodation for the best price. And you’ll save big when you bundle your travel together, like booking a car rental in Montgomery County along with your vacation property, into a Montgomery County vacation package.


Can I cancel my vacation home with Expedia?

Some accommodations are free to cancel and refundable if done so by a specific date, while others may be non-refundable. To make sure that you can get your money back on cancellations, use the “free cancellation” filter during your search. Contact our customer service portal if you need help.

Montgomery County Vacation Homes information

Number of reviews
429
Accommodation
51 Vacation Homes
Lowest Price
$169
Highest Price
$1,006

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