
House vacation rentals in Kendall County
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Top-rated house rentals in Kendall County
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Vacation rentals for every style
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Popular amenities for Kendall County house rentals
House rentals with a pool

Harbor Inn - Out of Office
The house was beautiful and perfectly clean. We had a great time enjoying the surroundings and going out to Ottawa and Starved Rock

Ottawa Oasis. Billiards. Pool. King Bed!
We look to stay at a property managed by Matt and Stephanie They are great to work with and always have a great place.

Pardizes Suites
My family and I enjoyed our stay at this lovely home. We felt extremely welcomed, comfortable, had everything we could have thought of and more. We definitely had a wonderful experience from the time we checked in the home until we checked out. The host, Lisa, was responsive and accommodating. Any issue that occurred, which there really weren’t many, she took care of right away. We had an issue with the temperature in the house due to not knowing how to work the thermostat but other than that everything exceeded our expectations. This home and host deserves the 5 stars I provided all the way. I look forward to staying in the future. Thank you for having us!

Glen Ellyn Home
The property was very nice. It was well maintained and our family with our grandson were very comfortable. If we were to have a negative comment is that the heat distribution was not even throughout the home. The upstairs where the three bedrooms were located was very warm and the kitchen, living room and family were quite chilly. However, this did not impede us having a comfortable stay.

Firepit•BBQ Grill•Spacious•30 mins to CHI•3 Kings
Such a great and responsive host for such a beautiful home! I definitely have to come back so I can enjoy the pool in the summer. It was a great home away from home. Spacius and well maintained. Would stay again!

On river|Quiet| King bed Immaculate| Nature parks
This private property, situated along the river in a tranquil and serene community, is truly remarkable. The rental matches the photographs perfectly, exuding warmth and charm while offering breathtaking views from every level. We appreciated the convenience of the open-concept kitchen, and having two full bathrooms along with a half bath on the main floor was a significant advantage. The master bedroom provided a comfortable retreat, allowing us to enjoy restful sleep. Although the sun did awaken us earlier on one occasion, the stunning view that greeted us upon opening the curtains made it worthwhile. The area boasts an array of excellent restaurants, all thoughtfully recommended and organized by our host. We relished our time at a winery for drinks and dined at several outstanding restaurants and a brewery located downtown, all of which were also suggested. We eagerly anticipate our return. Lynmari proved to be an exceptional host, and we extend our gratitude once more.

Pearl Street Pool House
The stay was wonderful and perfect for family fun! Michelle was very friendly and responsive. Lots to do and peaceful neighborhood

The Nautical Nest
We had an amazing stay at Paula’s place! She was very helpful with checking in and also very responsive. The house looks exactly like the pictures. Nice neighborhood. We would definitely stay here again!
Weekly house rentals

Your Unique Stay by the Tracks | LCP Collection
We definitely enjoyed our stay. The house beautiful and lots of room! Even though it’s right next to train track we literally only heard the train one time it’s a very quiet and beautiful home inside and out. There is also a beautiful walking trail very close by the water. The beds are absolutely so comfortable! We would definitely choose to stay here again if we are in the area!!!! Thank you so much !!!!

Moxie - w/ Game Room- 4 Kings, Sleeps 15
Fantastic house! Very spacious and had everything we needed for a family gathering/weekend!

Patriotic Cottage on the Hill
We thoroughly enjoyed our stay in Shelias home! it was a wonderful home away from home when in town for my daughter's wedding. The house was one of the cleanest properties I have stayed at and was very well stocked with anything you may need. Loved the antique feel mixed with modern furnishings.

Serene 5-Bedroom Retreat, Oswego
It was easy to communicate with host. He was very responsive. We stayed there with family and enough space for all. Thank you for hosting us.

Large Family Home w/Garage-King beds, Fast Wi-Fi
Our stay here was amazing! The neighborhood was peaceful and the house was everything we needed and more. We will definitely stay here again!

Skip the hotel! Relax here!
We stayed here while in town for a wedding at heritage prairie farms. It was a convenient spot to stay for a family with little kids.

Peaceful Farm House in South Plainfield
Everything was great, 100 % recommend, Host was very nice and will always respond fast.

Aurora Rental - Shiloh
This house worked well for us for an extended stay over the holidays. The 3 bedrooms upstairs and the kitchen and living room on the main floor provided plenty of space for our family to spread.
Private house rentals

Your Unique Stay by the Tracks | LCP Collection
We definitely enjoyed our stay. The house beautiful and lots of room! Even though it’s right next to train track we literally only heard the train one time it’s a very quiet and beautiful home inside and out. There is also a beautiful walking trail very close by the water. The beds are absolutely so comfortable! We would definitely choose to stay here again if we are in the area!!!! Thank you so much !!!!

Moxie - w/ Game Room- 4 Kings, Sleeps 15
Fantastic house! Very spacious and had everything we needed for a family gathering/weekend!

Lovely Ranch Bungalow
Nice older style accommodation with character, in a nice and friendly small town. The accommodation had everything we required for our stay.

Patriotic Cottage on the Hill
We thoroughly enjoyed our stay in Shelias home! it was a wonderful home away from home when in town for my daughter's wedding. The house was one of the cleanest properties I have stayed at and was very well stocked with anything you may need. Loved the antique feel mixed with modern furnishings.

Serene 5-Bedroom Retreat, Oswego
It was easy to communicate with host. He was very responsive. We stayed there with family and enough space for all. Thank you for hosting us.

Large Family Home w/Garage-King beds, Fast Wi-Fi
Our stay here was amazing! The neighborhood was peaceful and the house was everything we needed and more. We will definitely stay here again!

Skip the hotel! Relax here!
We stayed here while in town for a wedding at heritage prairie farms. It was a convenient spot to stay for a family with little kids.

Aurora Rental - Shiloh
This house worked well for us for an extended stay over the holidays. The 3 bedrooms upstairs and the kitchen and living room on the main floor provided plenty of space for our family to spread.
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- Matthiessen State Park
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park Zoo
- Willis Tower
- Lincoln Park
- Wicker Park
- Flossmoor Golf Club
- Brookfield Zoo
- The 606
- The Beverly Country Club
- Chicago Cultural Center
- Chicago History Museum
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