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Vacation Rentals in Montgomery County

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Top Vacation Rentals in Montgomery County

Vacation Home in Raymond

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

Vacation Home in Litchfield

10.0 out of 10, Exceptional, (17)
"Overflow holiday guests stayed at this cute, clean, comfortable home. A wonderful experience with exceptionally kind, engaged, owners! "
United States
Anonymous traveler
$170 nightly
The price is $180
Dec 7 - Dec 8
Total with taxes and fees
Jackson House; Pets Welcome

Vacation Home in 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.
$175 nightly
The price is $185
Jan 3 - Jan 4, 2026
Total with taxes and fees
Harrison House; Litchfield, IL; Pets welcome

Vacation Home in 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

Vacation Home in 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

Vacation Home in 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

Apartment in 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

Cabin in 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

Vacation Home in 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

Cabin in Irving

10.0 out of 10, Exceptional, (5)
"This was our second time staying here and it didn't dissapoint. "
United States
Kimberly D.
$372 nightly
The price is $394
Dec 11 - Dec 12
Total with taxes and fees
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving

Vacation Home in Litchfield

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

Vacation Home in Springfield

9.8 out of 10, Exceptional, (14)
"Beautiful property with everything we needed for a perfect stay. Very spacious!"
United States
Amy E.
$253 nightly
The price is $255
Dec 7 - Dec 8
Total with taxes and fees
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

Apartment in Carlinville

2.0 star property
$230 nightly
The price is $244
Dec 7 - Dec 8
Total with taxes and fees
Light Filled Loft on Town Square

Vacation Home in Springfield

8.8 out of 10, Excellent, (5)
"The house was very clean "
United States
Lance C.
$490 nightly
The price is $520
Dec 14 - Dec 15
Total with taxes and fees
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood

Vacation Home in 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.

Vacation Home in Springfield

10.0 out of 10, Exceptional, (6)
"Great roomy kitchen with large breakfast bar/counter eating space. Large wonderful shower with two shower heads. Washer & dryer in unit which is so convenient. Beds were very comfortable, - forgot to check what brand mattresses they were as we slept so well! Neighborhood is charming & walkable! "
United States
Rodney P.
Charming Springfield Stunner: a relaxing escape in peaceful Jerome Village

Cabin in Mulberry Grove

9.6 out of 10, Exceptional, (28)
"Perfect place for shinrin-yoku (forest bathing)!"
United States
Lori M.
$197 nightly
The price is $209
Dec 22 - Dec 23
Total with taxes and fees
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!

Vacation Home in 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.
$246 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

Vacation Home in 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.

Vacation Home in Springfield

9.6 out of 10, Exceptional, (21)
"This home is absolutely gorgeous. "
United States
Pamela B.
$253 nightly
The price is $255
Dec 7 - Dec 8
Total with taxes and fees
Charming Downtown Stay | Victorian Beauty & Modern Comfort
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

Discover your perfect Montgomery County vacation rental with Expedia

How many vacation rentals are available in Montgomery County?


Expedia has plenty of vacation rentals to choose from in and around  Montgomery County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Montgomery County?


The selection of Montgomery County vacation rentals we have selected for you start as low as $169 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Montgomery County?


Vacation rentals in Montgomery County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Montgomery County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Montgomery County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Montgomery County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Montgomery County?


Find vacation rentals in Montgomery County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Montgomery County.  


What amenities are available in a vacation rental in Montgomery County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Montgomery County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Montgomery County?   


Everytime is a great time to head to Montgomery County! Staying in a Montgomery County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Montgomery County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Montgomery County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Montgomery County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Montgomery County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.