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Montgomery County Holiday Rentals

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Our top choices for Montgomery County holiday rentals

A modern kitchen with white cabinets, a gas stove, and a microwave. There is a dining area with a wooden table and two chairs.

1. Edwards House; Litchfield, IL; Pets welcome

Edwards House; Litchfield, IL; Pets welcome
Litchfield
10.0 out of 10, Exceptional, (30 reviews)
"Very cozy, cute house!"
United States
Star
The price is AU$324
includes taxes & fees
13 Dec - 14 Dec
Edwards House; Litchfield, IL; Pets welcome
A room with a wooden floor, a sliding glass door leading to an outdoor patio with a table and chairs, and a broom leaning against the wall.

2. Harrison House; Litchfield, IL; Pets welcome

Harrison House; Litchfield, IL; Pets welcome
Litchfield
9.8 out of 10, Exceptional, (22 reviews)
"Loved this property. Will def be staying again. "
United States
Amanda G.
The price is AU$361
includes taxes & fees
13 Dec - 14 Dec
Harrison House; Litchfield, IL; Pets welcome
A modern kitchen with white cabinets, a dark wooden countertop, and a stainless steel sink.

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

State Street House; 3-br house; PETS WELCOME; Litchfield
Litchfield
9.6 out of 10, Exceptional, (21 reviews)
"Great place in a quiet charming town."
United States
William
The price is AU$435
includes taxes & fees
13 Dec - 14 Dec
State Street House; 3-br house; PETS WELCOME; Litchfield
A white door with a small window, two black chairs on a concrete porch, a black awning, and a black lantern on the wall.

4. The Relaxing House - Quiet 2 Bedroom Home

The Relaxing House - Quiet 2 Bedroom Home
Raymond
10.0 out of 10, Exceptional, (3 reviews)
"Lovely house, clean, good location, and very comfortable for our stay"
United States
Trudy K M.
The price is AU$287
includes taxes & fees
22 Nov - 23 Nov
The Relaxing House - Quiet 2 Bedroom Home
A modern kitchen with a dark wood floor, a white cabinet, a black bar stool, and a wooden table.

5. Route 66 house; Litchfield IL; Pets welcome

Route 66 house; Litchfield IL; Pets welcome
Litchfield
10.0 out of 10, Exceptional, (23 reviews)
"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 AU$322
includes taxes & fees
13 Dec - 14 Dec
Route 66 house; Litchfield IL; Pets welcome
A fire pit with four Adirondack chairs around it, set in a forested area.

6. 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
9.8 out of 10, Exceptional, (37 reviews)
"Went to visit kids who live in the area. Normally we get a hotel but decided to try doing something different. This was so much better than hotels and plan to go back next time we are down."
United States
Julie
The price is AU$311
includes taxes & fees
1 Dec - 2 Dec
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
A spacious room with a large bed, a dining table, and a television.

7. Light Filled Loft on Town Square.

Light Filled Loft on Town Square.
Carlinville
10.0 out of 10, Exceptional, (20 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is AU$459
includes taxes & fees
23 Nov - 24 Nov
Light Filled Loft on Town Square.
A porch with white wicker chairs, a small table, and a potted plant.

8. Grand Victorian Carlinville home on Rt. 66.

Grand Victorian Carlinville home on Rt. 66.
Carlinville
10.0 out of 10, Exceptional, (13 reviews)
"Great place to stay"
United States
Adam M.
The price is AU$915
includes taxes & fees
30 Nov - 1 Dec
Grand Victorian Carlinville home on Rt. 66.
A spacious room with a brick wall, a large bed, a ceiling fan, and two wicker lamps.

9. Unique loft in historic downtown

Unique loft in historic downtown
Vandalia
9.8 out of 10, Exceptional, (29 reviews)
"Beautiful loft, great place to stay!!"
United States
Sara
The price is AU$186
includes taxes & fees
15 Nov - 16 Nov
Unique loft in historic downtown
A garden with a bench, various plants, and a house in the background.

10. Home is on the original 1926-1930 Route 66 alignment

Home is on the original 1926-1930 Route 66 alignment
Girard
9.8 out of 10, Exceptional, (114 reviews)
"The house is very well maintained and cared for, the story and its relation to preserving R66 history is wonderful. The hosts were flexible with check-in timing, there is plenty of space for parking and the front porch swing adds a great vibe. Overall, a reasonably priced and comfortable stay! Would definitely recommend."
United States
Cory
The price is AU$252
includes taxes & fees
30 Nov - 1 Dec
Home is on the original 1926-1930 Route 66 alignment
A covered porch with a wooden floor, a white door, and two potted plants.

11. The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful house, our home away from home. We have stayed here many times and we will be back!"
United States
Janell M.
The price is AU$667
includes taxes & fees
22 Nov - 23 Nov
The Carlinville Cottage
A patio area with wicker furniture, a striped umbrella, and potted plants.

12. Cozy studio located in small town America, Bunker Hill, IL.

Cozy studio located in small town America, Bunker Hill, IL.
Bunker Hill
10.0 out of 10, Exceptional, (22 reviews)
"The apartment was very comfortable and cozy. We slept great and it was very nice to have a place to stay in Bunker Hill. "
United States
Erica L.
The price is AU$158
includes taxes & fees
16 Nov - 17 Nov
Cozy studio located in small town America, Bunker Hill, IL.
A two-story Victorian-style house with a wrap-around porch, a prominent tower with a conical roof, and a well-maintained front yard with flowering plants.

13. Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort
Springfield
10.0 out of 10, Exceptional, (23 reviews)
"It was a very nicely located and clean property large enough for a family to stay in as they visit the sites in Springfield."
United States
Joseph
The price is AU$245
includes taxes & fees
15 Nov - 16 Nov
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort
A room with a wooden floor, a cow-print armchair, a white door, and a hallway leading to a kitchen.

14. Beaver Inn - Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.

Beaver Inn - Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
Plainview
10.0 out of 10, Exceptional, (2 reviews)
"We were able to return to stay a few more days, and the cabin work perfectly for us. The kitchen has everything you need and all of the cookware was cleaned in great condition. The fridge, oven and dishwasher looked like they were brand new and everything worked exactly as expected. The bathroom has a tub which has a large "rain" type of shower head and there is plenty of hot water. The proximity to Beaver Dam is probably one of my favorite things about the house because my family loves to...
United States
Toni G.
The price is AU$266
includes taxes & fees
15 Nov - 16 Nov
Beaver Inn - Cozy 2-bedroom cabin at the entrance of Beaver Dam State Park.
A large, historic brick building with a prominent tower and arched windows, surrounded by well-maintained lawns and trees.

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

Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Springfield
10.0 out of 10, Exceptional, (65 reviews)
"The Rowland Suite was perfect for our stay in Springfield!"
United States
Robert S.
The price is AU$319
includes taxes & fees
15 Nov - 16 Nov
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
A wooden picnic table with a bench and a potted plant on top.

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

Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood
Springfield
9.6 out of 10, Exceptional, (24 reviews)
"Nice area and roomy fun house."
United States
Cheryl M.
The price is AU$729
includes taxes & fees
9 Dec - 10 Dec
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood
A pool table in a room with red walls, wooden cabinets, and a television.

17. Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!

Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
Springfield
9.2 out of 10, Wonderful, (9 reviews)
"Hosted our second bachelor here and it’s still one of the coolest places we’ve ever stayed! George is an awesome host!"
United States
Tyler B.
The price is AU$1,796
includes taxes & fees
21 Nov - 22 Nov
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
A large, historic brick building with a turret and multiple windows, surrounded by a well-maintained lawn and a metal fence.

18. Spacious Carriage House | Private Entrance | Historic & Stylish

Spacious Carriage House | Private Entrance | Historic & Stylish
Springfield
9.8 out of 10, Exceptional, (50 reviews)
"A very spacious lodging that was very clean and very comfortable. Will stay here again when in Springfield."
United States
Christine
The price is AU$310
includes taxes & fees
16 Nov - 17 Nov
Spacious Carriage House | Private Entrance | Historic & Stylish
A modern kitchen with a central island, stainless steel appliances, and a chandelier.

19. Peaceful Spaulding Orchard Home

Peaceful Spaulding Orchard Home
Springfield
9.6 out of 10, Exceptional, (8 reviews)
"The host was very helpful when we lost power during a storm."
United States
Kellie N.
The price is AU$525
includes taxes & fees
6 Dec - 7 Dec
Peaceful Spaulding Orchard Home
A kitchen with white cabinets, a stainless steel sink, a microwave, and a stove.

20. 2-bedroom house in Springfield

2-bedroom house in Springfield
Springfield
4.6 out of 10, (8 reviews)
"The bedrooms were a little smaller than I thought they wood be, but still great overall. Also, when we arrived it was raining and I parked in the driveway near the back door. I triedto go in through the back door, but the code for the front door didn't work for the back door."
United States
David V.
The price is AU$187
includes taxes & fees
16 Nov - 17 Nov
2-bedroom house in Springfield
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

Motel 6 Springfield, IL

Motel 6 Springfield, IL

10/10 Excellent
"Exelente servicio viejo en moto y me dejaron estacionarme a un lado de la puerta"
Ivan 1-night trip
Posted 1 hour ago
Motel 6 Springfield, IL

Find out more about Montgomery County

Everything you need to know about Montgomery County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Montgomery County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montgomery County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montgomery County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montgomery County holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Montgomery County holiday rentals we have chosen for you start as low as AU$245 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Montgomery County rentals

At Expedia, we put the best Montgomery County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Montgomery County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Montgomery County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Montgomery County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.