Top Cottages in Kendall County in 2026

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Top cities in Kendall County

A calm lake with reflections of trees and sky, surrounded by greenery and a clear blue sky.

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Our top choices for Kendall County cottages

A hot tub with a wooden deck and metal railing, surrounded by a covered area with a metal roof.

1. Westmont Home w/ Hot Tub! Walk to Metra Station

Westmont

"Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my...

Rick

A single-story building with a covered porch, a front door, and a small outdoor seating area with two chairs and a table.

2. Peaceful Warrenville Home: 1 Mi to Herrick Lake!

Warrenville

A log cabin with a deck featuring outdoor seating and a large window.

3. Fox River Luxury Estate: Pool, Sauna & Eagle Views

Ottawa

A single-story house with a garage, a brick exterior, and a well-maintained lawn.

4. Private Plainfield Retreat w/ Gas Grill + Patio

Plainfield

A living room with a dining table, two sofas, a TV, and a lamp.

5. Rural Seneca House w/ Yard Near I-80

Seneca

Maria

A single-story house with a stone facade, a red garage door, and a small front porch.

6. Glendale Heights Home With Office and Backyard!

Glendale Heights

JINYOUNG

A modern living room with a grey sofa, two pink armchairs, a round coffee table, and a fireplace.

7. Home w/ Office + Yard: 25 Mi to Downtown Chicago!

Glen Ellyn

A modern living room with a large TV, a sofa, and a dining area with chairs and a table.

8. Fire Pit & Grill: Family Home on Fox River Trail!

St. Charles

A two-story house with a covered porch, a small patio with chairs, and a well-maintained lawn.

9. Captain`s Quarters - 179 Leeward Way, Cottage #6

Ottawa

10. Huck Finn #26

Ottawa

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Top reviews in Kendall County

A multi-story hotel with a parking lot and a landscaped area.

Holiday Inn Express & Suites Aurora - Naperville by IHG

Downtown Aurora

10/10 Excellent

Kimberly

A Best Western hotel with a sign, parking area, and a building with multiple windows.

Best Western Oswego Hotel

Oswego

10/10 Excellent

William J

A bed with white bedding and a wooden headboard.

Holiday Inn Express & Suites Yorkville by IHG

Yorkville

10/10 Excellent

Douglas

An American Inn with a red roof, stone pillars, and a covered entrance.

AmericInn by Wyndham Oswego

Oswego

10/10 Excellent

Marcus

Super 8 by Wyndham Yorkville

Yorkville

10/10 Excellent

Amanda

A large stone building with a covered entrance, snow-covered trees, and a clear sky.

The Montcler Hotel - Redberri Luxury Collection

Sandwich

10/10 Excellent

Daniel

A modern hotel with a "HOME 2 Suites by Hilton" sign, outdoor seating area, and a well-lit entrance.

Home2 Suites by Hilton Joliet/Plainfield

Joliet

10/10 Excellent

Tonia

La Quinta Inn & Suites by Wyndham Shorewood

Joliet

10/10 Excellent

David

A Hampton Inn hotel with a modern brick facade, a covered entrance, and a parking lot.

Hampton Inn DeKalb, IL

DeKalb

10/10 Excellent

My husband and I stayed here while visiting our daughter in the area. The room was very clean and everything was updated and nice. The bed was comfortable, the hotel was quiet and peaceful; everything was well lit and very safe. We didn’t eat the breakfast, but did do a walk through of it and it looked and smelled delicious and other visitors seemed to be enjoying it. The staff were friendly and helpful throughout our stay. We’ll definitely be staying again when we visit in the future!

Carolyn

A Hampton Inn & Suites building with a stone facade, a neon sign, and a parking lot.

Hampton Inn & Suites Chicago/Aurora

West Aurora

10/10 Excellent

Rodney

A multi-story hotel with a prominent entrance and a parking lot.

Country inn & Suites by Radisson, Bolingbrook- Romeoville, I-55

Bolingbrook

10/10 Excellent

I recently had the pleasure of staying at Country Inn & Suites in Bolingbrook, and I must say, it exceeded my expectations! The hotel has a fresh look, with modern decor that creates a welcoming atmosphere. The staff were incredibly friendly and attentive, making my stay even more enjoyable. Additionally, the rooms and common areas were nice and clean, which added to the overall comfort. I would highly recommend this hotel for anyone looking for a pleasant stay in the area!

Sarah

A Hampton Inn & Suites hotel entrance with a clear sign, a covered walkway, and a landscaped area with plants.

Hampton Inn & Suites Chicago/St. Charles

St. Charles

10/10 Excellent

Such a comfortable stay! We had an event at Pheasant Run and didn't want to stay on site. The beds at the Hampton were SO comfortable! The staff were all very friendly and really seemed to enjoy being there. The breakfast was fabulous for a hotel breakfast. Such a variety- and so much more than toast and cereal. Loved the hot breakfast variety that changed each morning of our stay! My only suggestion is to add another waffle station to make sure that everyone who wants a waffle has time to make...

Anonymous traveler

A Fairfield Inn & Suites hotel with a modern design, featuring a stone facade and a covered entrance.

Fairfield Inn & Suites by Marriott Chicago Bolingbrook

Bolingbrook

10/10 Excellent

Christine

Cottages in Kendall County

Change your mind

Treat yourself

Be picky

Top cities in Kendall County

Yorkville

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Kendall County cottages

1. Westmont Home w/ Hot Tub! Walk to Metra Station

2. Peaceful Warrenville Home: 1 Mi to Herrick Lake!

3. Fox River Luxury Estate: Pool, Sauna & Eagle Views

4. Private Plainfield Retreat w/ Gas Grill + Patio

5. Rural Seneca House w/ Yard Near I-80

6. Glendale Heights Home With Office and Backyard!

7. Home w/ Office + Yard: 25 Mi to Downtown Chicago!

8. Fire Pit & Grill: Family Home on Fox River Trail!

9. Captain`s Quarters - 179 Leeward Way, Cottage #6

10. Huck Finn #26

Top reviews in Kendall County

Holiday Inn Express & Suites Aurora - Naperville by IHG

10/10 Excellent

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