Vacation rentals in Montgomery County

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Top-rated vacation rentals in Montgomery County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Fillmore

4.94 out of 5 average rating, 66 reviews

Pheasant Valley Farms

Enjoy your stay in your very own farmhouse. Nestled in rolling hills, with views of the flowing creek and fields. Just 6 miles East of Hillsboro, IL & 45 minutes from Springfield, IL Enjoy hiking, fishing, golf, boating and relaxing on the porch. The farmhouse has 1 bedroom with a queen bed and comfortable sofa sleeper (double) in the living room. There is also a bed/futon in the summer kitchen (separate structure, no bathroom). Best used in cooler weather, no A/C. It is more of a man cave

Guest favorite

Barn in Bingham

4.98 out of 5 average rating, 40 reviews

Down on the Farm

Remote area that's about 15 min from Interstate 70. Quiet & peaceful w/minimal road traffic. When it's warm, you can fish at our pond or visit nearby Ramsey Lake State Park to fish. During the farming season you may hear tractors & combines. There are Amish in the area & a local Amish market. Go for walks in our wooded area. Relax on a private deck in the evening. Queen bed, full bed, as well as a couch w/matching loveseat. One small pet under 15 pounds allowed: Please read our strict pet rules

Guest favorite

Home in Hillsboro

4.94 out of 5 average rating, 36 reviews

Historic Blackman-Evans Home

Centrally located on Main Street close to downtown Hillsboro. Step back in time where past meets present when you visit this historic home. You are surrounded by period furniture, while enjoying modern amenities such as A/C, WiFi, TVs, and luxury bedding. Built in the southern style, this creole-inspired cottage with a local stone foundation and original black walnut floors, stair case and wood work transports you to another time. Not suitable for small children, workgroups or pets. NO PETS.

Guest favorite

Home in Litchfield

4.96 out of 5 average rating, 216 reviews

Harrison House; PETS WELCOME; FENCED YARD

Find all of our Litchfield homes by searching "softstays" on the internet. The Harrison House is a beautifully decorated 2-bedroom house that is in a safe neighborhood. WE ARE PET FRIENDLY. The beds are 12” queen memory foam. All the furnishings are new or nearly new. It has a fenced in backyard. KIDS ARE WELCOME. There is a back deck. There is no cable. There is 100 meg wireless internet. There is a ring camera on the porch. You will hear trains. Two tracks run thru middle of town

Guest favorite

Home in Litchfield

4.94 out of 5 average rating, 357 reviews

Rt 66 House; PETS WELCOME; FENCED YARD

Find all of our Litchfield homes by searching "softstays" on the internet. The Rt 66 house is on Historic Rt 66. It is 50 miles North of St. Louis; Right off I-55: PET FRIENDLY; FENCED BACK YARD. There is plenty of room to park a large U-Haul trailer. It is loaded with warm and updated furnishings. It has LOTS of 5* reviews. It has a thick memory foam queen bed. It has a coffee bar. You will hear trains. Two tracks run thru middle of town. 100 meg internet.

Guest favorite

Rental unit in Hillsboro

4.97 out of 5 average rating, 92 reviews

Lakehouse Studio Unit - The Historic Red Rooster Inn

The building has been renovated and two very special overnight accommodations have been created. The location is close to 4th of July Point, Sherwood Forest Campground, Glenn Shoals Lake South Marina, Hillsboro Country Club Golf Course, and is just a few miles from downtown Hillsboro. The tranquil lake setting will prove to be a peaceful retreat from hectic life and a wonderful place to unwind while visiting local family and friends

Guest favorite

Home in Fillmore

4.95 out of 5 average rating, 37 reviews

Private Getaway House w/ Pond & Trails on 10 Acres

Our place includes a recently remodeled home on 10 Acres in the middle of a country setting. There is a large patio area overlooking a half acre pond (fishing is catch and release only) right out of the front door. The property includes cleared trails to explore on, large grassy areas, a gravel driveway with ample parking, and a propane BBQ and deck out the kitchen door. Also has a ramp on the backside for wheelchair accessibility.

Guest favorite

Cottage in Vandalia

4.82 out of 5 average rating, 315 reviews

The Lake House

Quaint, cozy, cottage nestled on Beautiful Lake Vandalia. 1870’s farm house with all original decor. Full size granite bar located in 4 seasons room overlooking lake. Full size commercial kitchen. Stand up walk in shower, washer and dryer. Plenty of free safe parking. Perfect for a night stay or a full week vacation with family.

Guest favorite

Loft in Hillsboro

4.92 out of 5 average rating, 59 reviews

Downtown Hillsboro Loft

Two bedroom loft space in downtown Hillsboro located above an art gallery and next to a coffee shop and candy store! It’s also walking distance from a brewery, movie theater, live theater and several local retail stores. The living space displays works of local artisans to complement the hint of mid-century style.

Guest favorite

Cabin in Hillsboro

4.94 out of 5 average rating, 180 reviews

3 Bedroom, 2 bath cabin with deck and hot tub

Take it easy at this unique and tranquil getaway. Nestled across from Hillsboro Country Club Golf Course this location will have scenic views and be a great place to unwind and get away. Located near Sherwood Forest Campground, Glenn Shoals Lake, Hillsboro Lake as well as city parks.