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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, (29 reviews)
"Very cozy, cute house!"
United States
Star
The price is HK$934
HK$1,546 total
includes taxes & fees
4 Nov - 5 Nov
Edwards House; Litchfield, IL; Pets welcome
A two-story house with a front porch, a green door, and the number 408 on the right side.

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 HK$1,302
HK$2,012 total
includes taxes & fees
6 Nov - 7 Nov
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.

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 HK$1,687
HK$2,577 total
includes taxes & fees
1 Nov - 2 Nov
State Street House; 3-br house; PETS WELCOME; Litchfield
A single-story house with a front door, two windows, a small porch, and a paved driveway.

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 HK$1,020
HK$1,596 total
includes taxes & fees
1 Nov - 2 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 HK$1,137
HK$1,812 total
includes taxes & fees
14 Nov - 15 Nov
Route 66 house; Litchfield IL; Pets welcome
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, (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 HK$1,010
HK$1,819 total
includes taxes & fees
18 Nov - 19 Nov
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
A patio area with wicker furniture, a striped umbrella, and potted plants.

7. 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, (21 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 HK$565
HK$973 total
includes taxes & fees
1 Nov - 2 Nov
Cozy studio located in small town America, Bunker Hill, IL.
A garden with a bench, various plants, and a house in the background.

8. 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, (113 reviews)
"Great,quiet,lovely"
United States
Patti H.
The price is HK$628
HK$1,430 total
includes taxes & fees
13 Nov - 14 Nov
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.

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 HK$621
HK$1,074 total
includes taxes & fees
29 Oct - 30 Oct
Unique loft in historic downtown
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island with bar stools.

10. 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 HK$1,726
HK$3,957 total
includes taxes & fees
30 Oct - 31 Oct
The Carlinville Cottage
A spacious room with a large bed, a dining table, and a television.

11. Light Filled Loft on Town Square.

Light Filled Loft on Town Square.
Carlinville
10.0 out of 10, Exceptional, (19 reviews)
"Very clean, nice location. Would stay here again. "
United States
Regina S.
The price is HK$1,765
HK$2,619 total
includes taxes & fees
29 Oct - 30 Oct
Light Filled Loft on Town Square.
A two-story house with a wrap-around porch, a central entrance with a door, and a chimney.

12. 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 HK$3,020
HK$5,289 total
includes taxes & fees
11 Nov - 12 Nov
Grand Victorian Carlinville home on Rt. 66.
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, (22 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 HK$1,244
HK$1,427 total
includes taxes & fees
2 Nov - 3 Nov
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort
A large, historic brick building with a prominent tower and arched windows, surrounded by well-maintained lawns and trees.

14. 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 HK$1,565
HK$1,781 total
includes taxes & fees
1 Nov - 2 Nov
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
A modern kitchen with a central island, stainless steel appliances, and a chandelier.

15. 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 HK$1,185
HK$2,827 total
includes taxes & fees
29 Oct - 30 Oct
Peaceful Spaulding Orchard Home
A room with a bed, a TV, a desk, and a chair.

16. 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 HK$530
HK$1,060 total
includes taxes & fees
2 Nov - 3 Nov
2-bedroom house in Springfield
A modern living room with a sofa, armchair, coffee table, and a dining area with a kitchen in the background.

17. Newly Renovated Unit in Central Spfld! #204

Newly Renovated Unit in Central Spfld! #204
Springfield
6.0 out of 10, (1 review)
"Unfortunately in today’s world, it’s hard to function, especially meetings & contracts without WiFi. I stayed Wednesday - Wednesday , 7 nights. I only had WiFi for 1 night. The TV would not turn on, the maintenance man ( who was very nice) brought a new remote. After he left the WiFi was not working, he came the next day & reset the router. By the next morning it was down again. Very delayed communication at that point, they were tired of me. Then I was ghosted. I rarely like to give a...
United States
Elizabeth G.
Newly Renovated Unit in Central Spfld! #204
A spacious kitchen with wooden cabinets, a dining area with chairs, and a staircase leading to another level.

18. 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, (21 reviews)
"Nice area and roomy fun house."
United States
Cheryl M.
The price is HK$2,192
HK$4,027 total
includes taxes & fees
1 Nov - 2 Nov
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood
A white building with a number '308' and a logo on the door.

19. Unique apartment in historic downtown

Unique apartment in historic downtown
Vandalia
9.8 out of 10, Exceptional, (26 reviews)
"This is a cute little apartment in the cutest little town. It is such a quiet spot to stay. We enjoyed how close it was to everything. We enjoyed our stay in Vandalia!"
United States
Shauney S.
The price is HK$682
HK$1,056 total
includes taxes & fees
15 Nov - 16 Nov
Unique apartment in historic downtown
A spa room with a wooden hot tub, a glass partition, and a painting on the wall.

20. 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 HK$7,453
HK$10,393 total
includes taxes & fees
3 Nov - 4 Nov
Sports complex w/ Hot Tub located near Scheels Sports Park and Lincolns home!
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

La Quinta Inn & Suites by Wyndham Springfield IL

La Quinta Inn & Suites by Wyndham Springfield IL

10/10 Excellent
"The room was spotless. The staff was very nice."
Pamela 1-night trip
Posted 15 hours ago
La Quinta Inn & Suites by Wyndham Springfield IL