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Vacation Homes in Kendall County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Top Cities in Kendall County

A stone bridge over a calm river, surrounded by lush greenery and buildings.
Vacation HomesVacation Homes

Oswego

Oswego

Our top choices for Kendall County vacation homes

Smart TV, video games

1. Furnished Private home in Aurora sleeps 9 guests

Furnished Private home in Aurora sleeps 9 guests
Aurora
9.2 out of 10, Wonderful, (121 reviews)
"The host was very prompt at responding to all our needs. The location was perfect. Very roomy. Would definitely stay again"
United States
Tracie E.
Furnished Private home in Aurora sleeps 9 guests
Interior

2. Charming 2-bedroom house in DeKalb

Charming 2-bedroom house in DeKalb
DeKalb
8.8 out of 10, Excellent, (13 reviews)
"hi such a great place to stay for the week! we loved it here!!"
United States
Avra H.
Charming 2-bedroom house in DeKalb
Exterior

3. Cozy Mother-in-Law Suite w/Laundry, Kitchenette, Walk-In Closet, and Rain Shower

Cozy Mother-in-Law Suite w/Laundry, Kitchenette, Walk-In Closet, and Rain Shower
Joliet
10.0 out of 10, Exceptional, (3 reviews)
"Such a clean, quiet, comfortable, roomy place to stay. The host, Ben, is great. I will definitely try to stay here next time, provided it’s not already booked."
United States
Max L.
The price is AED 301
AED 552 total
includes taxes & fees
15 Sep - 16 Sep
Cozy Mother-in-Law Suite w/Laundry, Kitchenette, Walk-In Closet, and Rain Shower
Coffee/tea maker, microwave, dishwasher, toaster

4. Spacious open concept home w/ game room + firepit

Spacious open concept home w/ game room + firepit
Winfield
9.8 out of 10, Exceptional, (99 reviews)
"Great location"
United States
Ross S.
Spacious open concept home w/ game room + firepit
Exterior

5. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (70 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is AED 672
AED 1,207 total
includes taxes & fees
10 Sep - 11 Sep
✽ Charming Cottage ✽ close to College/Town/Station
Property grounds

6. "St Geneva" Private With River View! 10 min From Lamplight Equestrian Center

"St Geneva" Private With River View! 10 min From Lamplight Equestrian Center
St. Charles
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful location and very comfortable. Michael is a great host. We would stay there again."
United States
Anne H.
"St Geneva" Private With River View! 10 min From Lamplight Equestrian Center
Interior

7. Great Location! Walking Distance to So Much!

Great Location! Walking Distance to So Much!
Ottawa
8.6 out of 10, Excellent, (4 reviews)
"The host, Kim, was accommodating and easy to communicate with. I asked for early check-in and later check-out (within reason), and since the place was not rented to others, she graciously accepted.The townhouse was clean and supplied with all the stated accessories. Perhaps, a little more dishwashing fluid and bathroom soaps would be great.The neighborhood was quite during our stay and the townhouse was conveniently located within a walking distance of downtown Ottawa.The only reason I rated it...
United States
Mansour G.
Great Location! Walking Distance to So Much!
Dining

8. Modern Home in Trendy Neighborhood 40 from Downtown Chicago

Modern Home in Trendy Neighborhood 40 from Downtown Chicago
Plainfield
9.6 out of 10, Exceptional, (26 reviews)
"Great place to stay with extended family. Clean home and comfortable home."
United States
Aliasgar D.
Modern Home in Trendy Neighborhood 40 from Downtown Chicago
Smart TV

9. Spacious Chicagoland Retreat with Hot Tub + Fireplace Sleeps 8+

Spacious Chicagoland Retreat with Hot Tub + Fireplace Sleeps 8+
Carol Stream
9.0 out of 10, Wonderful, (6 reviews)
"The house was super comfortable with everything we needed for a wonderful getaway. My partner and I enjoyed the hot tub and our dogs enjoyed the beautiful backyard. Lisa was super communicative and the space felt like home away from home with lots of spaces to relax and enjoy quiet connection. Definitely recommend this as a great rental for families and couples!"
United States
Joshua T.
Spacious Chicagoland Retreat with Hot Tub + Fireplace Sleeps 8+
Dining

10. Modern 4-bedroom house in peaceful Westmont area

Modern 4-bedroom house in peaceful Westmont area
Westmont
10.0 out of 10, Exceptional, (5 reviews)
"We had an amazing stay!"
United States
Analuisa R.
Modern 4-bedroom house in peaceful Westmont area
Coffee/tea maker, fridge, microwave, oven

11. Fun, Spacious, NO STAIRS, Garage, WIFI, Sleeps 8max – Ideal for Families & Crews

Fun, Spacious, NO STAIRS, Garage, WIFI, Sleeps 8max – Ideal for Families & Crews
Montgomery
9.8 out of 10, Exceptional, (13 reviews)
"The place was as advertised very clean and close to a bunch of restaurants and entertainment. The hosts were very prompt in responding to any questions we had. Great stay good location we will definitely consider staying at this home when we go back"
United States
Victor R.
Fun, Spacious, NO STAIRS, Garage, WIFI, Sleeps 8max – Ideal for Families & Crews
Coffee/tea maker, fridge, microwave, oven

12. Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly

Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly
Westmont
10.0 out of 10, Exceptional, (3 reviews)
"Clean, Family friendly yes"
United States
ronald M.
The price is AED 1,072
AED 2,277 total
includes taxes & fees
8 Sep - 9 Sep
Modern Spacious 4BR Home Near Chicago • Sleeps 10 • Family & Pets Friendly
Property grounds

13. Riverview Retreat- Engler's Escape in Wilmington on the Kankakee River

Riverview Retreat- Engler's Escape in Wilmington on the Kankakee River
Wilmington
8.8 out of 10, Excellent, (6 reviews)
"This house was perfect for where we wanted to stay. It’s right on the water and had a great deck to sit and relax. The house was clean and had plenty of the amenities that you will need. The location was great right on Route 66. Make shure you stop in downtown and do some antique shopping. I would definitely stay here again!"
United States
Dennis S.
Riverview Retreat- Engler's Escape in Wilmington on the Kankakee River
Private kitchen

14. This space close to the Northern Illinois University and I-88 Highway.

This space close to the Northern Illinois University and I-88 Highway.
DeKalb
9.0 out of 10, Wonderful, (20 reviews)
"It had all the amenities that we needed for an extended stay. "
United States
Bonnie K.
This space close to the Northern Illinois University and I-88 Highway.
Dining

15. Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath

Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
Aurora
The price is AED 651
AED 1,449 total
includes taxes & fees
21 Sep - 22 Sep
Family-Friendly 3BR Home • Sleeps 6 • 2.5 Bath
Smart TV, fireplace, books

16. Ottawa Family Nest – Fresh Eggs, Cozy, Relax!

Ottawa Family Nest – Fresh Eggs, Cozy, Relax!
Ottawa
10.0 out of 10, Exceptional, (7 reviews)
"Very nice place and close to the downtown area in ottawa and a short drive to Starve Rock. Rooms aver very spacious and the sun room is great to relax in. Our kids loved the chicken coop and fresh eggs. Overall a great place to stay."
United States
Eduardo H.
Ottawa Family Nest – Fresh Eggs, Cozy, Relax!
Outdoor dining

17. Fox River House

Fox River House
Plano
10.0 out of 10, Exceptional, (14 reviews)
"Really enjoy the stay very quite very clean "
United States
Donna
Fox River House
Exterior

18. Step into the Past: Stylish 1970s Mid-Century VRBO for a Vintage Getaway!

Step into the Past: Stylish 1970s Mid-Century VRBO for a Vintage Getaway!
Glen Ellyn
10.0 out of 10, Exceptional, (13 reviews)
"This property exceeded all expectations. It was spotlessly clean, odor free and very well appointed. The 1974 vibe was exceptional and fit our reunion weekend perfectly as did the location. Commnication with the host was perfect and the check in process as seemless. We could not have had a better experience. Thank you!"
United States
Janet K.
Step into the Past: Stylish 1970s Mid-Century VRBO for a Vintage Getaway!
Coffee/tea maker, fridge, microwave, oven

19. River View, walk to town, stylish, Spacious

River View, walk to town, stylish, Spacious
St Charles
10.0 out of 10, Exceptional, (25 reviews)
"This property was fantastic. Everything you could need was available in the house. The view of the river was very nice and the location was perfect. Very close to town and St. Charles is a charming little community."
United States
William W.
River View, walk to town, stylish, Spacious
Marina

20. The West End Wonder - Modern/Walkable Heritage Harbor Area!

The West End Wonder - Modern/Walkable Heritage Harbor Area!
Ottawa
9.4 out of 10, Exceptional, (6 reviews)
"The property was beautiful and perfect for my family."
United States
Suzette
The West End Wonder - Modern/Walkable Heritage Harbor Area!
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 Kendall County Hotel Reviews

Hyatt Lodge Oak Brook Chicago

Hyatt Lodge Oak Brook Chicago

10/10 Excellent
"Love the service and location"
James 5-night trip
Posted 11 hours ago
Hyatt Lodge Oak Brook Chicago

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