Compare Winnetka Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in Winnetka
![Mccormick Place Guest House](https://images.trvl-media.com/lodging/23000000/22680000/22671000/22670906/78f1725e_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Mccormick Place Guest House
3643 South Indiana Avenue, Chicago, IL
The price is $125 per night
$125
per night
Jun 17 - Jun 18
Mccormick Place Guest House features free WiFi in public areas and a picnic area. You can take advantage of free parking if you drive. Additional amenities include barbecue grills and a garden.
Parking included
Free WiFi
![Wrigleyville Inn](https://images.trvl-media.com/lodging/92000000/91440000/91438500/91438413/941870bf_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Wrigleyville Inn
914 W Newport Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $248 per night
$248
per night
Jul 8 - Jul 9
Guests of Wrigleyville Inn enjoy free WiFi in public areas, a terrace, and laundry facilities. Free parking is included with your stay.
Parking included
Free WiFi
![Chicago Guest House on Henderson Street](https://images.trvl-media.com/lodging/11000000/10020000/10014300/10014287/73452743_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Chicago Guest House on Henderson Street
1330 W Henderson Street, Chicago, IL
A local mainstay since 1886, Chicago Guest House on Henderson Street offers free WiFi in public areas, a terrace, and laundry facilities. Free parking is available if you drive. Additional amenities include a picnic area, a garden, and barbecue grills.
Parking included
Free WiFi
Oakwood at 73 E. LAKE
73 East Lake Street, Chicago, IL
Stay at this guesthouse in Chicago. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
![A5 Luxurious Garden Unit Near Chicago](https://images.trvl-media.com/lodging/46000000/45820000/45812600/45812573/c8f6248c_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
A5 Luxurious Garden Unit Near Chicago
Guests staying at this guesthouse enjoy features like a gym.
Air conditioning
Gym
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.
Hotel Options in Winnetka
![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/41255425_y.jpg?impolicy=resizecrop&rw=402&ra=fit)
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is $161 per night from Jul 1 to Jul 2
$161
per night
Jul 1 - Jul 2
7.6/10 Good! (6,948 reviews)
![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/1676cf3d_y.jpg?impolicy=resizecrop&rw=402&ra=fit)
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is $191 per night from Jul 2 to Jul 3
$191
per night
Jul 2 - Jul 3
8/10 Very Good! (2,390 reviews)
![River Hotel](https://images.trvl-media.com/lodging/3000000/2680000/2675400/2675313/a97325e3_y.jpg?impolicy=resizecrop&rw=402&ra=fit)
River Hotel
75 East Wacker Drive, Chicago, IL
The price is $171 per night from Jun 30 to Jul 1
$171
per night
Jun 30 - Jul 1
8.6/10 Excellent! (2,951 reviews)
Winnetka Guest Houses essential information
Accommodation | 8 Guest Houses |
---|---|
Lowest Price | $125 |
Highest Price | $248 |
Popular accommodation | Mccormick Place Guest House, Wrigleyville Inn, MultiManor: A Renovated Bucktown Coach House, Chicago Guest House on Henderson Street, Oakwood at 73 E. LAKE, A5 Luxurious Garden Unit Near Chicago, Oakwood at AMLI RIVER NORTH, Oakwood Chicago River North |