Search Vacation Homes in Winnetka

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Vacation Homes in Winnetka

Exterior
A quiet stay while you are away
A quiet stay while you are away
9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
United States
Karigan H.
The price is AED 214
AED 707 total
includes taxes & fees
29 Oct - 30 Oct
A quiet stay while you are away
Fridge, microwave, oven, stovetop
Getaway Near ORD With Great Local Amenities
Getaway Near ORD With Great Local Amenities
8.8 out of 10, Excellent, (3)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
The price is AED 256
AED 1,015 total
includes taxes & fees
28 Oct - 29 Oct
Getaway Near ORD With Great Local Amenities
Dining
Quaint Bungalow, near Great Lakes Naval Base
Quaint Bungalow, near Great Lakes Naval Base
9.8 out of 10, Exceptional, (65)
"Great place and great price. Lots of restaurants around. Minutes from the highway for city access."
United States
Joseph B.
The price is AED 496
AED 1,218 total
includes taxes & fees
26 Oct - 27 Oct
Quaint Bungalow, near Great Lakes Naval Base
Exterior detail
Master qtr close to nature & easy urban facilities
Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (69)
"Beautiful, quiet space."
United States
Mary
The price is AED 327
AED 682 total
includes taxes & fees
3 Nov - 4 Nov
Master qtr close to nature & easy urban facilities
Fridge, microwave, oven, stovetop
Cozy Home by O'Hare + EV Plug
Cozy Home by O'Hare + EV Plug
10.0 out of 10, Exceptional, (2)
"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."
United States
Michael H.
The price is AED 423
AED 1,042 total
includes taxes & fees
28 Oct - 29 Oct
Cozy Home by O'Hare + EV Plug
Fridge, microwave, oven, stovetop
Luxury House minutes away from O'Hare and Downtown Chicago
Luxury House minutes away from O'Hare and Downtown Chicago
10.0 out of 10, Exceptional, (1)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is AED 647
AED 2,091 total
includes taxes & fees
27 Oct - 28 Oct
Luxury House minutes away from O'Hare and Downtown Chicago
Smart TV
Enamored in Elmhurst
Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
The price is AED 780
AED 1,812 total
includes taxes & fees
26 Oct - 27 Oct
Enamored in Elmhurst
Private kitchen
Value Stay: Home - 2 Bedrooms
Value Stay: Home - 2 Bedrooms
2.0 star property
The price is AED 367
AED 891 total
includes taxes & fees
26 Oct - 27 Oct
Value Stay: Home - 2 Bedrooms
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
7.8 out of 10, Good, (11)
"Very nice place "
United States
Elliot H.
The price is AED 545
AED 894 total
includes taxes & fees
26 Oct - 27 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Cookware/dishes/utensils
Designer Furnished + Game Room | LCP Collection
Designer Furnished + Game Room | LCP Collection
10.0 out of 10, Exceptional, (3)
"The home is clean, appears to have been recently updated on the inside. Nice kitchen with everything you need. Conveniently located between the city and suburbs."
United States
Pat S.
The price is AED 716
AED 1,658 total
includes taxes & fees
27 Oct - 28 Oct
Designer Furnished + Game Room | LCP Collection
Paper towels, dining tables
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
10.0 out of 10, Exceptional, (2)
"Was nice would recommend staying with you folks"
United States
Richard W.
The price is AED 605
AED 1,418 total
includes taxes & fees
28 Oct - 29 Oct
PROMO 10% WEEKLY 15% MONTHLYOFFCozy Family Retreat: King Beds, Garage, Fast WiFi
Fridge, microwave, stovetop, dishwasher
Classic Forest Park Foursquare < 1 Mi to Blue Line
Classic Forest Park Foursquare < 1 Mi to Blue Line
2.0 star property
The price is AED 459
AED 1,467 total
includes taxes & fees
26 Oct - 27 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
Fridge, microwave, oven, stovetop
Updated Spacious Home -Near NWU- Hospitals+More
Updated Spacious Home -Near NWU- Hospitals+More
10.0 out of 10, Exceptional, (3)
"We had a great stay, nice neighborhood, nice home & clean home, fantastic communication with the host. Would stay here again!"
United States
Heather C.
The price is AED 617
AED 1,560 total
includes taxes & fees
11 Nov - 12 Nov
Updated Spacious Home -Near NWU- Hospitals+More
Exterior
Cozy Outdoor Space + BBQ | LCP Collection
Cozy Outdoor Space + BBQ | LCP Collection
9.0 out of 10, Wonderful, (2)
"Good"
United States
Bridget O.
The price is AED 635
AED 1,886 total
includes taxes & fees
26 Oct - 27 Oct
Cozy Outdoor Space + BBQ | LCP Collection
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm
Modern Victorian Vibes ❤️ | Character & Charm
10.0 out of 10, Exceptional, (25)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is AED 840
AED 2,135 total
includes taxes & fees
11 Nov - 12 Nov
Modern Victorian Vibes ❤️ | Character & Charm
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!
Wonderful in Wood Dale, right by O’Hare airport!
10.0 out of 10, Exceptional, (14)
"Great property and great host!"
United States
Darin H.
The price is AED 658
AED 1,456 total
includes taxes & fees
26 Oct - 27 Oct
Wonderful in Wood Dale, right by O’Hare airport!
Fridge, microwave, oven, stovetop
NEW! 10-min to Downtown | LCP Collection
NEW! 10-min to Downtown | LCP Collection
9.6 out of 10, Exceptional, (10)
"Great place - smooth rental, check-in, communications."
United States
Janice B.
The price is AED 834
AED 2,120 total
includes taxes & fees
11 Nov - 12 Nov
NEW! 10-min to Downtown | LCP Collection
Fridge, microwave, oven, stovetop
North Chi retreatNavySaunaTiki BarGames
North Chi retreatNavySaunaTiki BarGames
10.0 out of 10, Exceptional, (12)
"Very nice and newly remodeled property. Would definitely recommend. Property owner was pleasant and attended to maintenance issues promptly. Pool table and air hockey tables were fun to play on. There is even a sauna on the property but we did not use it. Great location for being near the Naval base."
United States
Bernadette B.
The price is AED 885
AED 1,991 total
includes taxes & fees
10 Nov - 11 Nov
North Chi retreatNavySaunaTiki BarGames
Fridge, microwave, oven, stovetop
Near O’Hare/King Bed/Fenced yard/FirePit+Game room
Near O’Hare/King Bed/Fenced yard/FirePit+Game room
9.8 out of 10, Exceptional, (31)
"The stay at the property was very pleasant. The host was very responsive and checked in on us to ensure we had everything we needed during our time here. I would definitely recommend. "
United States
MJTrot 7.
The price is AED 729
AED 1,589 total
includes taxes & fees
26 Oct - 27 Oct
Near O’Hare/King Bed/Fenced yard/FirePit+Game room
Microwave, stovetop, dishwasher
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
10.0 out of 10, Exceptional, (1)
"Great location and perfect set up for a family size Vaca!! Loved it!"
United States
Robin C.
The price is AED 771
AED 1,756 total
includes taxes & fees
26 Oct - 27 Oct
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winnetka Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"LOVED the room and the view was spectacular! The location could not have been any more convenient. Lobby was beautiful. Our room had a separate living room with bay windows looking out over Lake Michigan and the city. The bedroom was fantastic with a comfortable bed and pillows. We slept so well. Nice separate bathroom and an extra walk-in closet. I was so pleased that I didn’t want to leave even after 3 nights. I’ll definitely stay here again. "
April 3-night trip
Posted 13 hours ago
Congress Plaza Hotel