Montgomery County Vacation Rentals

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Featured Vacation Homes in Montgomery County

Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds
Property grounds

Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay! The place is so clean and cute and cozy! We definitely felt right at home! Can’t wait to stay again soon! Thank you! "
Lake Shelbyville Corn Crib is a Charming 2-bedroom house with fishing ponds
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Stately Victorian house with a corner turret and ornate front porch, surrounded by a well-maintained lawn and metal fence.

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

10.0 out of 10, Exceptional, (48)
"Great hosts and accommodations!"
The price is CA $300
CA $344 total
includes taxes & fees
Aug 20 - Aug 21
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Home is on the original 1926-1930 Route 66 alignment
Stroll through the beautifully maintained garden, surrounded by a variety of flowering plants and lush greenery.

Home is on the original 1926-1930 Route 66 alignment

10.0 out of 10, Exceptional, (90)
"Great Stay with family a couple of blocks away"
The price is CA $99
CA $237 total
includes taxes & fees
Aug 9 - Aug 10
Home is on the original 1926-1930 Route 66 alignment
Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood
Stroll through the serene garden, surrounded by lush greenery and vibrant plants.

Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood

10.0 out of 10, Exceptional, (1)
"Great place to stay ! The home was clean, cozy, and had everything you could need from the multiple charging cubes to bathroom and kitchen essentials. If you appreciate antique furnishings this home has it. The backyard was nice and had cute pathways between the many trees and garden. Our dog loved all the smells too ! The host is quick to respond and easy going. Highly recommend ! "
Whitt’s End -- a spacious private lodging in a historic Springfield neighborhood
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood
Cozy retreat with a large bed, featuring a white headboard and plush pillows, and a unique art piece above.

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

8.0 out of 10, Very good, (1)
"Our stay was very good…. Had plenty of entertainment at your beautiful home. "
The price is CA $425
CA $765 total
includes taxes & fees
Aug 20 - Aug 21
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Relax in a cozy corner with a round table and two comfortable chairs, enjoying a view of the city.

Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

10.0 out of 10, Exceptional, (2)
"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."
The price is CA $931
CA $1,650 total
includes taxes & fees
Aug 14 - Aug 15
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Craftsman styled home in the heart of downtown Highland
Enjoy cooking in this well-equipped kitchen with a central island, stove, and ample counter space.

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (59)
"We had a wonderful stay! Plenty of room and Jennifer did a fantastic job of communicating with us! "
Craftsman styled home in the heart of downtown Highland
Jackson House; Pets Welcome
Kitchen features a central island with a stove and oven, flanked by cabinetry with gold handles.

Jackson House; Pets Welcome

10.0 out of 10, Exceptional, (13)
"Overflow holiday guests stayed at this cute, clean, comfortable home. A wonderful experience with exceptionally kind, engaged, owners! "
The price is CA $158
CA $247 total
includes taxes & fees
Aug 21 - Aug 22
Jackson House; Pets Welcome
Plainview Vineyard Retreat by StayLage
Welcome to the charming Fasting Room of Plainview Vineyard, featuring a traditional design with a cozy porch and a unique wine bottle sculpture.

Plainview Vineyard Retreat by StayLage

2.0 star property
10.0 out of 10, Exceptional, (1)
"Quiet place to relax after a long day. Clean and will rent again if given the choice. "
The price is CA $140
CA $594 total
includes taxes & fees
Aug 13 - Aug 14
Plainview Vineyard Retreat by StayLage
State Street House; 3-br house; PETS WELCOME; Litchfield
Enjoy cooking in this well-equipped kitchen with a stainless steel refrigerator, wooden countertop, and dark backsplash.

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

10.0 out of 10, Exceptional, (7)
"Even cuter in person! It was the perfect stay for 4 girls traveling from various states. The house was clean, owners were communicative, and check out process was easy. We would stay here again. "
The price is CA $191
CA $306 total
includes taxes & fees
Aug 21 - Aug 22
State Street House; 3-br house; PETS WELCOME; Litchfield
Victorian Carlinville home on Rt. 66
Relax on the classic porch with two comfortable chairs and a small table, surrounded by lush greenery and a charming door.

Victorian Carlinville home on Rt. 66

10.0 out of 10, Exceptional, (8)
"We will stay there again if we're in the area."
Victorian Carlinville home on Rt. 66
The Conkling House in the Old Aristocracy Hill Neighborhood
Classic two-story lodging with a central pediment and double doors, set amidst a well-manicured lawn.

The Conkling House in the Old Aristocracy Hill Neighborhood

8.0 out of 10, Very good, (6)
"We enjoyed our stay. This is a beautiful house, and it is lovely to have seven bedrooms for 11. There is not a conventional stovetop or oven. people. Note th We would stay here again."
The Conkling House in the Old Aristocracy Hill Neighborhood
Charming Springfield Stunner: a relaxing escape in peaceful Jerome Village
Enjoy cooking in this well-equipped kitchen with a gas stove, microwave, and ample countertop space.

Charming Springfield Stunner: a relaxing escape in peaceful Jerome Village

10.0 out of 10, Exceptional, (1)
"This home was beautiful! Absolutely stunning and completely clean. There was nothing out of place and everhything in the description was true with no exaggeration. The owner was very responsive and compassionate...beyond words! This was probably the best stay I've experienced. "
Charming Springfield Stunner: a relaxing escape in peaceful Jerome Village
Rainbow Retreat ~ 3-bedroom fun loving home full of color!
Cozy retreat with a large bed, potted plant, and framed artwork.

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

9.8 out of 10, Exceptional, (6)
"Perfect place to stay with little ones. They have a toy box and room to play. Had a good stay."
Rainbow Retreat ~ 3-bedroom fun loving home full of color!
Gold Room at the Feitshans House
Stately Victorian house with a prominent gabled roof and symmetrical facade, featuring multiple windows and a central bay window.

Gold Room at the Feitshans House

8.8 out of 10, Excellent, (3)
"The home was relaxing and very pleasant. Also accessible to so many Springfield sites. We would definitely stay again."
Gold Room at the Feitshans House
Edwards House; Litchfield, IL; Pets welcome
Cozy retreat with a neatly made bed, two bedside tables, and a light-colored rug.

Edwards House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (18)
"Mike and Amy have a beautiful cozy place to stay. My partner and I had a wonderful time and were super comfy during our stay!"
The price is CA $143
CA $231 total
includes taxes & fees
Aug 21 - Aug 22
Edwards House; Litchfield, IL; Pets welcome
Private country setting with large indoor pool
Relax by the indoor pool surrounded by comfortable seating and natural light.

Private country setting with large indoor pool

9.4 out of 10, Exceptional, (16)
"Greatly enjoyed the property for our holiday get together for family from different directions. The kids especially enjoyed the pool and game room (also the sound system)!One mention would be that the kitchen could use new cooking items, particularly pans and cookie sheets. The bedrooms and bathrooms were quite satisfactory. Overall, it was a great place for our family! Thank you"
Private country setting with large indoor pool
Blue Room at the Feitshans House
Stately Victorian house with a central entrance, flanked by two smaller windows, and a decorative archway.

Blue Room at the Feitshans House

10.0 out of 10, Exceptional, (1)
"The Blue Room at the Feitshans House was beautiful, elegant and very accomodating for our weekend stay in Springfield. It is centrally located to all the downtown historic activities and eateries are just a short drive in all directions. The home is tastefully decorated and has all the amenities one needs for a short or long term stay. We enjoyed the historical books and antiques throughout the home. It was easy to get in and out and parking is more than adequate. We had a wonderful stay in the...
The price is CA $80
CA $217 total
includes taxes & fees
Sep 8 - Sep 9
Blue Room at the Feitshans House
THE NEST getaways&gatherings, beach/lake sleeps 20+
Relax on the elevated deck with benches, taking in the serene views of the surrounding trees and water.

THE NEST getaways&gatherings, beach/lake sleeps 20+

10.0 out of 10, Exceptional, (37)
"The house was wonderful and the beach a lot of fun. It was the perfect family vacation spot!"
THE NEST getaways&gatherings, beach/lake sleeps 20+
Charming Springfield Home: 2 Mi to Downtown
Step out onto the covered porch and enjoy the view of the surrounding neighborhood.

Charming Springfield Home: 2 Mi to Downtown

10.0 out of 10, Exceptional, (18)
"We were in town for a couple days and really enjoyed our stay there. The house was nice and clean and convenient for downtown visits. "
The price is CA $84
CA $328 total
includes taxes & fees
Aug 14 - Aug 15
Charming Springfield Home: 2 Mi to Downtown
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

Sleep Inn Springfield West

Sleep Inn Springfield West

10/10 Excellent
"The staff seem to anticipate our needs. Very thoughtful."
petrick 1-night trip
Posted 1 day ago
Sleep Inn Springfield West