Holiday Rentals in Montgomery County

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Featured Holiday Rentals in Montgomery County

Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks
Exterior

Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks

9.4 out of 10, Exceptional, (9)
"Very relaxing fun place to stay!"
The price is €326
includes taxes & fees
29 Jul - 30 Jul
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks
Private country setting with large indoor pool
A heated pool

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
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving
Smart TV, fireplace, table football

New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving

10.0 out of 10, Exceptional, (3)
"This was our second time staying here and it didn't dissapoint. "
The price is €326
includes taxes & fees
1 Aug - 2 Aug
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving
Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield
Smart TV, fireplace

Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield

Loft Living - Small Town Charm 3-bedroom loft in beautiful Downtown Litchfield
Jackson House; Pets Welcome
Fridge, microwave, oven, stovetop

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 €158
includes taxes & fees
17 Aug - 18 Aug
Jackson House; Pets Welcome
Harrison House; Litchfield, IL; Pets welcome
Property grounds

Harrison House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (11)
"We loved the house, plenty of space and it was furnished with everything we could need. Highly recommend!"
The price is €162
includes taxes & fees
3 Aug - 4 Aug
Harrison House; Litchfield, IL; Pets welcome
State Street House; 3-br house; PETS WELCOME; Litchfield
Private kitchen

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

10.0 out of 10, Exceptional, (6)
"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 €191
includes taxes & fees
30 Jul - 31 Jul
State Street House; 3-br house; PETS WELCOME; Litchfield
Route 66 house; Litchfield IL; Pets welcome
Fridge, microwave, oven, stovetop

Route 66 house; Litchfield IL; Pets welcome

10.0 out of 10, Exceptional, (15)
"Cute little place we were visiting our grandchildren who live in the area and we all had a great time the house is well decorated so cute and everything you need is there. We will check to see if this place is available every time we visit the grandchildren."
The price is €147
includes taxes & fees
17 Aug - 18 Aug
Route 66 house; Litchfield IL; Pets welcome
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
Exterior

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

10.0 out of 10, Exceptional, (45)
"Great hosts and accommodations!"
The price is €217
includes taxes & fees
29 Jul - 30 Jul
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Exterior

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

10.0 out of 10, Exceptional, (24)
"We loved everything about this place!"
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY
Beautiful and Cozy Apartment in Springfield- 2 Bedroom
Fridge, microwave, oven, stovetop

Beautiful and Cozy Apartment in Springfield- 2 Bedroom

10.0 out of 10, Exceptional, (1)
"The apartment was very clean and in a good neighborhood close to downtown attractions. There was a minor issue with the wi-fi but the property manager was quick to resolve the issues. Would recommend. "
Beautiful and Cozy Apartment in Springfield- 2 Bedroom
Home is on the original 1926-1930 Route 66 alignment
Terrace/patio

Home is on the original 1926-1930 Route 66 alignment

10.0 out of 10, Exceptional, (89)
"Great Stay with family a couple of blocks away"
The price is €142
includes taxes & fees
5 Aug - 6 Aug
Home is on the original 1926-1930 Route 66 alignment
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
Exterior

Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!

9.8 out of 10, Exceptional, (20)
"Cozy and perfect for a weekend get away out of the city "
The price is €168
includes taxes & fees
12 Aug - 13 Aug
Tiny Cabin in the Woods - Firepit - just off I-70 - Pets Welcome!
Craftsman styled home in the heart of downtown Highland
Fridge, microwave, oven, stovetop

Craftsman styled home in the heart of downtown Highland

10.0 out of 10, Exceptional, (58)
"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
Charming Springfield Home: 2 Mi to Downtown
House (2 Bedrooms) | Interior

Charming Springfield Home: 2 Mi to Downtown

3.0 star property
10.0 out of 10, Exceptional, (2)
"The cottage was nicely renovated and decorated. It had a good supply of necessities and very comfortable!"
The price is €189
includes taxes & fees
14 Aug - 15 Aug
Charming Springfield Home: 2 Mi to Downtown
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
View from property

Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury

9.8 out of 10, Exceptional, (12)
"It was a treat to go back to this property after a day of sight seeing. Very convenient location, clean and comfortable apartment, updated with modern amenities but still full of charming antiques. We would stay here again!"
The price is €217
includes taxes & fees
28 Jul - 29 Jul
Timeless Elegance | Walk to Capitol & Attractions | Historic Luxury
Old Aristocracy Hill 1BR Quiet Apartment Downtown!
Fridge, microwave, oven, stovetop

Old Aristocracy Hill 1BR Quiet Apartment Downtown!

7.0 out of 10, Good, (2)
"Dislikes: Chairs provided were not comfortable, couch would have been better suitable. Bathroom sink was clogged and did not drain, leaving other guests hair behind. Bathroom door did not shut. Only one towel provided for entire stay per guest. Choice of soaps provided were less than desirable. Lamps provided did not work along with various outlets. Several times had to call office due to being locked out of main building. Likes: Location ideal for downtown commute. Washer and dryer...
The price is €147
includes taxes & fees
31 Jul - 1 Aug
Old Aristocracy Hill 1BR Quiet Apartment Downtown!
Beach-themed rental with many activities within walking distance.
Private kitchen

Beach-themed rental with many activities within walking distance.

10.0 out of 10, Exceptional, (2)
"Very Clean and comfortable!"
The price is €167
includes taxes & fees
28 Jul - 29 Jul
Beach-themed rental with many activities within walking distance.
Lake House off Route 66
Exterior

Lake House off Route 66

9.0 out of 10, Wonderful, (2)
"The home itself was fantastic—clean, well-maintained, and exactly as pictured. The host was responsive and friendly, and the location right on the lake made for a relaxing stay. The only downside, and the reason I’m giving 4 stars instead of 5, is that there’s a camper in the front yard with people staying in it. This wasn’t disclosed in the listing, and it made the experience feel a bit less private and more awkward than expected. If that had been communicated up front, it would’ve helped set...
The price is €196
includes taxes & fees
2 Aug - 3 Aug
Lake House off Route 66
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
Dining

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 €886
includes taxes & fees
17 Aug - 18 Aug
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location
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

Holiday Inn Express & Suites Litchfield West by IHG

Holiday Inn Express & Suites Litchfield West by IHG

10/10 Excellent
"Super nice clean, beds GOOD, no complaints, not my first time staying here, will be there again next month. Great Place!!! "
Steven 1-night trip
Posted 23 hours ago
Holiday Inn Express & Suites Litchfield West by IHG