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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

B&B in Winnetka

Private kitchen
The Sono Chicago
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (479)
"Loved the shared kitchen access! "
United States
Jennifer M
The price is AED 608
AED 714 total
includes taxes & fees
27 Oct - 28 Oct
The Sono Chicago
Staircase
The Publishing House B&B
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (186)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
The price is AED 730
AED 824 total
includes taxes & fees
16 Nov - 17 Nov
The Publishing House B&B
Free WiFi, bed sheets
Dorothy's
Dorothy's
3.0 star property
8.4 out of 10, Very Good, (84)
"Clean room beautiful.yards convenient"
United States
Daniel
The price is AED 208
AED 373 total
includes taxes & fees
27 Oct - 28 Oct
Dorothy's
Exterior
House 5863 - Chicago Bed and Breakfast
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, (488)
"Super cute and comfortable place to stay. Erick was very communicative and welcoming. Great snack bar!"
United States
Kirstyn
The price is AED 418
AED 693 total
includes taxes & fees
27 Oct - 28 Oct
House 5863 - Chicago Bed and Breakfast
Exterior
The Villa Toscana
The Villa Toscana
2.5 star property
7.8 out of 10, Good, (612)
"Amazing location for the North Halsltead area, but also good for transport in and around the city. Uniquely weird location and place. "
United States
Scott
The price is AED 228
AED 414 total
includes taxes & fees
12 Nov - 13 Nov
The Villa Toscana
Property entrance
Wicker Park Inn
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
Wicker Park Inn
Lobby sitting area
Villa D' Citta
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (110)
"Great place"
United States
Jeffrey
The price is AED 841
AED 987 total
includes taxes & fees
10 Nov - 11 Nov
Villa D' Citta
Front of property
Ray's Bucktown B&B
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (380)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
The price is AED 599
AED 676 total
includes taxes & fees
26 Oct - 27 Oct
Ray's Bucktown B&B
Property entrance
Harvey House Bed & Breakfast
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (118)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
United States
Bethany
The price is AED 848
AED 942 total
includes taxes & fees
3 Nov - 4 Nov
Harvey House Bed & Breakfast
5 bedrooms, free WiFi, bed sheets
Five bedroom - 3 bath - Sleeps 12
Five bedroom - 3 bath - Sleeps 12
The price is AED 2,149
AED 3,655 total
includes taxes & fees
11 Nov - 12 Nov
Five bedroom - 3 bath - Sleeps 12
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 Winnetka Hotel Reviews

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Check in was quick and easy. I ordered dinner from the hotel restaurant and it was decent. Elevators are very slow to get to your floor. No ice machines but they will deliver ice to your room. Room was spacious but very cold. Thermostat set on 78 and it was still very drafty. The bathroom did not seem to have heat in it at all. Area was walkable and convenient. Evening security guard was kind. "
Kimberly 2-night trip
Posted 10 hours ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

Searching for B&Bs in Winnetka?
If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your vacation. When you venture out to explore Winnetka, Lake Michigan is a some popular sight to visit.
How do you know if a B&B is the best choice for you?
With attentive service, opportunities to meet other guests, and hearty breakfasts, B&Bs all have a truly one-of-a-kind setting.
What are the best bed and breakfasts in Winnetka?
Here are some B&Bs in the surrounding area: Dorothy's: 7 rooms. 12.1 mi (19.5 km) from the heart of Winnetka.House 5863 - Chicago Bed and Breakfast: 7 rooms. 9 mi (14.5 km) from the downtown core. Enjoy the designer toiletries and private yard. The Villa Toscana: 9 rooms. Situated 12.1 mi (19.5 km) from the heart of Winnetka. The Sono Chicago: 7 rooms. 14.6 mi (23.5 km) from the heart of downtown. Enjoy the rooftop terrace and fireplace in the lobby. Ray's Bucktown B&B: 11 rooms. Located 13.2 mi (21.2 km) from the core of Winnetka. Enjoy the free cooked breakfast and rooftop terrace.
When should I stay at a B&B in Winnetka?
When you're planning your escape to Winnetka, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 30°F. Average annual precipitation for Winnetka is 48 inches.
What is there to do in Winnetka?
When you want to spend some time in the great outdoors, Lake Michigan and Maple Street Beach are some notable spots. You might put Chocolate Box and Elder Lane Beach on your list if you want to see more of the area.
How can I get to and around Winnetka?
Mapping out your trip in and around Winnetka is easy with these transportation options. Fly into Chicago, IL (PWK-Chicago Executive), which is located 8.4 mi (13.5 km) away from the heart of the city. Otherwise, look for flights into Chicago O'Hare Intl. Airport (ORD), which is 12.5 mi (20.2 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.