Search Holiday Rentals in Montgomery County

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Top Holiday Rentals in Montgomery County

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

9.4 out of 10, Exceptional, (10)
"This house was perfect for our annual Guys Weekend (a few dads in their 40s and 50s).Plenty of room, clean, and quiet. We appreciated the fussball table, dart board, and comfortable living room with a big TV for sports. Fishing was good too, caught quite a few bass, and we got a kick out of the boat. We all agreed this place was great, and would recommend to all. "
The price is £266
includes taxes & fees
11 Aug - 12 Aug
Walk Me Out in the “Morning Dew”. Secluded A-Frame Cabin on Pond with 3 decks

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

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 £139
includes taxes & fees
17 Aug - 18 Aug
Jackson House; Pets Welcome

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 £174
includes taxes & fees
17 Aug - 18 Aug
State Street House; 3-br house; PETS WELCOME; Litchfield

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 £302
includes taxes & fees
14 Aug - 15 Aug
New Minglewood is our Cozy 3-bedroom cabin with WiFi, AC in lovely Irving

Harrison House; Litchfield, IL; Pets welcome

10.0 out of 10, Exceptional, (11)
"Everything was in excellent shape and the fenced yard was great for the pups."
The price is £142
includes taxes & fees
11 Aug - 12 Aug
Harrison House; Litchfield, IL; Pets welcome

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 £129
includes taxes & fees
17 Aug - 18 Aug
Route 66 house; Litchfield IL; Pets welcome

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

10.0 out of 10, Exceptional, (48)
"Great hosts and accommodations!"
The price is £192
includes taxes & fees
20 Aug - 21 Aug
Grand Historic Retreat | 3BR Suite | Modern Comfort & Classic Charm

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

LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

10.0 out of 10, Exceptional, (25)
"We loved everything about this place!"
LAKE SHELBYVILLE PRIVATE FISHING GET-AWAY

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 £132
includes taxes & fees
8 Aug - 9 Aug
Home is on the original 1926-1930 Route 66 alignment

Unique loft in historic downtown

10.0 out of 10, Exceptional, (19)
"Loft was super clean, spacious and quiet. Building built in 1861 so very unique space. Plenty of street parking. Air conditioning was great and a selection of restaurants and pubs down the street. Lots of nicely restored building-one can feel the history! Host communicated immediately and check in/out easy and seamless. "
The price is £111
includes taxes & fees
24 Aug - 25 Aug
Unique loft in historic downtown

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 £426
includes taxes & fees
20 Aug - 21 Aug
Abe's Hideaway - Arcade, Hot Tub, Home Theater - Quiet upscale neighborhood

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 £938
includes taxes & fees
14 Aug - 15 Aug
Luxury Historic Escape | Whole House Sleeps 18 | Walkable Location

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

Capital Suite on 6th Street - King Bed / Downtown!

9.2 out of 10, Wonderful, (9)
"Very good value for a basic apartment in a good location."
The price is £129
includes taxes & fees
1 Sept - 2 Sept
Capital Suite on 6th Street - King Bed / Downtown!

Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

2.0 star property
10.0 out of 10, Exceptional, (5)
"Everything was really nice and as described. Would stay there again!"
The price is £151
includes taxes & fees
20 Aug - 21 Aug
Elegant Historic Stay | Walk to Capitol & Attractions | Modern Comfort

Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks

2.0 star property
10.0 out of 10, Exceptional, (2)
"5 senior ladies on a girl trip and we couldn't have picked a better place to stay, everything was PERFECT. The home was beautiful and sooo comfortable, the location was just right. Would absolutely stay there again."
The price is £290
includes taxes & fees
18 Aug - 19 Aug
Spacious Historic Escape | 4BR Luxury | Walk to Downtown & Landmarks

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 £166
includes taxes & fees
14 Aug - 15 Aug
Charming Springfield Home: 2 Mi to Downtown

Beach-themed rental with many activities within walking distance.

10.0 out of 10, Exceptional, (2)
"Very Clean and comfortable!"
The price is £152
includes taxes & fees
8 Aug - 9 Aug
Beach-themed rental with many activities within walking distance.
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