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Montgomery County Vacation Rentals

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Our top choices for Montgomery County vacation 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, (29 reviews)
"Very cozy, cute house!"
United States
Star
The price is CA $170
CA $264 total
includes taxes & fees
Oct 16 - Oct 17
Edwards House; Litchfield, IL; Pets welcome
A single-story house with a front door, two windows, a small porch, and a paved driveway.

2. The Relaxing House - Quiet 2 Bedroom Home

The Relaxing House - Quiet 2 Bedroom Home
Raymond
10.0 out of 10, Exceptional, (2 reviews)
"This brand new home was perfect for our holiday vacation. Kristin and Terry were wonderful hosts, and there were many lovely personal touches throughout the home. The space was comfortable and we had everything we needed during our stay. Check-in was easy and the entire experience was stress free. We highly recommend this property! "
United States
Janelle P.
The price is CA $178
CA $284 total
includes taxes & fees
Oct 21 - Oct 22
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.

3. 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 CA $173
CA $267 total
includes taxes & fees
Oct 13 - Oct 14
Route 66 house; Litchfield IL; Pets welcome
A two-story house with a front porch, a green door, and the number 408 on the right side.

4. Harrison House; Litchfield, IL; Pets welcome

Harrison House; Litchfield, IL; Pets welcome
Litchfield
10.0 out of 10, Exceptional, (21 reviews)
"Loved this property. Will def be staying again. "
United States
Amanda G.
The price is CA $181
CA $285 total
includes taxes & fees
Oct 13 - Oct 14
Harrison House; Litchfield, IL; Pets welcome
A living room with a black leather couch, a wooden coffee table, and a bookshelf. There is a dining area visible through an archway with a wooden table and chairs.

5. 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, (20 reviews)
"Great place in a quiet charming town."
United States
William
The price is CA $264
CA $405 total
includes taxes & fees
Oct 13 - Oct 14
State Street House; 3-br house; PETS WELCOME; Litchfield
A modern kitchen with granite countertops, stainless steel appliances, and decorative wall shelves.

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, (36 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 CA $152
CA $294 total
includes taxes & fees
Oct 19 - Oct 20
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
A garden with a bench, various plants, and a house in the background.

7. 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, (111 reviews)
"absolutely delightful, love it every time, will be back"
United States
connie b.
The price is CA $114
CA $257 total
includes taxes & fees
Oct 14 - Oct 15
Home is on the original 1926-1930 Route 66 alignment
A spacious room with a brick wall, a large bed, a ceiling fan, and two wicker lamps.

8. Unique loft in historic downtown

Unique loft in historic downtown
Vandalia
9.8 out of 10, Exceptional, (27 reviews)
"Excellent place to stay, have stayed multiple times."
United States
Derek L.
The price is CA $113
CA $195 total
includes taxes & fees
Oct 13 - Oct 14
Unique loft in historic downtown
A patio area with wicker furniture, a striped umbrella, and potted plants.

9. 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, (20 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 CA $103
CA $177 total
includes taxes & fees
Oct 16 - Oct 17
Cozy studio located in small town America, Bunker Hill, IL.
A spacious room with a large island kitchen, a cozy seating area with a sofa and armchairs, and a bed with a view of the city through arched windows.

10. Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.

Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
Carlinville
10.0 out of 10, Exceptional, (18 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is CA $321
CA $470 total
includes taxes & fees
Oct 13 - Oct 14
Light Filled Loft on Town Square, formerly Karla’s Jewelry bldg.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island with bar stools.

11. The Carlinville Cottage

The Carlinville Cottage
Carlinville
10.0 out of 10, Exceptional, (22 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 CA $314
CA $716 total
includes taxes & fees
Oct 30 - Oct 31
The Carlinville Cottage
Private kitchen

12. Newly Renovated Unit in Central Spfld! #301

Newly Renovated Unit in Central Spfld! #301
Springfield
The price is CA $114
CA $354 total
includes taxes & fees
Oct 13 - Oct 14
Newly Renovated Unit in Central Spfld! #301
A room with a bed, a TV, a desk, and a chair.

13. 2-bedroom house in Springfield

2-bedroom house in Springfield
Springfield
4.6 out of 10, (7 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 CA $96
CA $193 total
includes taxes & fees
Oct 13 - Oct 14
2-bedroom house in Springfield
Private kitchen

14. Newly Renovated Unit in Central Spfld! #303

Newly Renovated Unit in Central Spfld! #303
Springfield
The price is CA $114
CA $354 total
includes taxes & fees
Oct 13 - Oct 14
Newly Renovated Unit in Central Spfld! #303
Private kitchen

15. Newly Renovated Unit in Central Spfld! #304

Newly Renovated Unit in Central Spfld! #304
Springfield
The price is CA $114
CA $354 total
includes taxes & fees
Oct 13 - Oct 14
Newly Renovated Unit in Central Spfld! #304
Private kitchen

16. Newly Renovated Unit in Central Spfld! #201

Newly Renovated Unit in Central Spfld! #201
Springfield
6.0 out of 10, (1 review)
"This unit was not clean. The shower and one of the beds had hair, floors were sticky throughout, and dishes were left in the dishwasher. The fees charged added up to a full nights stay! I tried to inquire about these and received no response. The building was also very loud. For the money I paid, I expected much better!"
United States
Kelli F.
The price is CA $114
CA $347 total
includes taxes & fees
Oct 13 - Oct 14
Newly Renovated Unit in Central Spfld! #201
A two-story house with a wrap-around porch, a central entrance with a door, and a chimney.

17. 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 CA $549
CA $961 total
includes taxes & fees
Oct 18 - Oct 19
Grand Victorian Carlinville home on Rt. 66.
A modern living room with a flat-screen TV, grey upholstered sofas, a coffee table, and a kitchen area with wooden cabinets.

18. Newly Renovated Unit in Central Spfld! #101

Newly Renovated Unit in Central Spfld! #101
Springfield
The price is CA $104
CA $341 total
includes taxes & fees
Oct 13 - Oct 14
Newly Renovated Unit in Central Spfld! #101
Private kitchen

19. Newly Renovated Unit in Central Spfld! #202

Newly Renovated Unit in Central Spfld! #202
Springfield
The price is CA $134
CA $382 total
includes taxes & fees
Nov 2 - Nov 3
Newly Renovated Unit in Central Spfld! #202
A living room with a gray sofa, round coffee table, and two armchairs. There is a round mirror on the wall and a window with blinds.

20. Newly Renovated Unit in Central Spfld! #203

Newly Renovated Unit in Central Spfld! #203
Springfield
The price is CA $134
CA $382 total
includes taxes & fees
Nov 2 - Nov 3
Newly Renovated Unit in Central Spfld! #203
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

Crowne Plaza Springfield by IHG

Crowne Plaza Springfield by IHG

10/10 Excellent
"The staff were all friendly and helpful"
Diana 1-night trip
Posted 5 hours ago
Crowne Plaza Springfield by IHG

Find out more about Montgomery County

Everything you need to know about Montgomery County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Montgomery County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Montgomery County vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. 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.  The selection of Montgomery County vacation rentals we have selected for you start as low as CA $193 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 vacation 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 vacation.

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.