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Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 24 B&B in Winnetka with updated reviews, rates, and availability.

The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (538)
"Very cool place. For a come and go place for me it was perfect. I never saw anyone on the property."
The price is SAR 226
SAR 416 total
includes taxes & fees
1 Apr - 2 Apr
The Villa Toscana
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (169)
"Was surprisingly excellent "
The price is SAR 718
SAR 811 total
includes taxes & fees
21 Apr - 22 Apr
The Publishing House B&B
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (343)
"This used to be Ray's photo studio, because he was a professional photographer. That probably wouldn't matter to most people, but I am also a professional photographer and I really enjoyed talking with Ray about birds and his travels. I really appreciated the indoor parking, and the breakfasts were very large. The staff was very friendly and helpful in explaining everything that we had access to in the building. It would be a great stop for kids because of all the games available. Loved...
The price is SAR 673
SAR 759 total
includes taxes & fees
31 Mar - 1 Apr
Ray's Bucktown B&B
Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.0 out of 10, Very Good, (25)
"We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!"
The price is SAR 196
SAR 361 total
includes taxes & fees
2 Apr - 3 Apr
Dorothy's
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (449)
"This bed and breakfast was an absolutely breathtaking gem that surpassed every expectation we had, delivering an experience that went well beyond what the photographs could capture. From the moment we arrived, we were struck by the stunning beauty of the place, which seemed to offer everything one could possibly desire in a cozy getaway. The owners were the epitome of hospitality—warm, welcoming, and genuinely sweet—always ready to lend a hand with anything we needed, whether it was local...
The price is SAR 545
SAR 639 total
includes taxes & fees
7 Apr - 8 Apr
The Sono Chicago
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (241)
"Very cute and dainty place to stay! Lovely staff! Very clean and homey! "
The price is SAR 815
SAR 957 total
includes taxes & fees
30 Mar - 31 Mar
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Unique experience staying within a block of DePaul School of Music. Lovely property with open kitchen and great breakfast/coffee. Nice outdoor area with fire pit. Stayed in Capone suite which was comfortable but noisy as it was downstairs just below the kitchen. Note that private bath is down the hall as this wasn’t explained well when I booked. Would stay again and I do recommend."
The price is SAR 772
SAR 907 total
includes taxes & fees
2 Apr - 3 Apr
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (109)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is SAR 867
SAR 962 total
includes taxes & fees
31 Mar - 1 Apr
Harvey House Bed & Breakfast
Wrigleyville Suites Room 1
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 1

2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
The price is SAR 539
SAR 948 total
includes taxes & fees
30 Mar - 31 Mar
Wrigleyville Suites Room 1
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (472)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
House 5863 - Chicago Bed and Breakfast
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is SAR 289
SAR 618 total
includes taxes & fees
1 Apr - 2 Apr
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is SAR 299
SAR 630 total
includes taxes & fees
21 Apr - 22 Apr
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is SAR 344
SAR 685 total
includes taxes & fees
28 Mar - 29 Mar
Villa Dubois Guest House Room 4
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is SAR 344
SAR 685 total
includes taxes & fees
31 Mar - 1 Apr
Villa Dubois Guest House Room 2
Room in Town house Rogers Park
Smart TV

Room in Town house Rogers Park

Room in Town house Rogers Park
Wrigleyville Suites Room 3
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 3

2.0 star property
The price is SAR 496
SAR 892 total
includes taxes & fees
29 Mar - 30 Mar
Wrigleyville Suites Room 3
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is SAR 496
SAR 892 total
includes taxes & fees
29 Mar - 30 Mar
Wrigleyville Suites Room 2
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (134)
"Our family of 4 enjoyed our short stay here. Great location that has everything you need a walking distance away. Jon was great to communicate with."
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is SAR 410
SAR 772 total
includes taxes & fees
31 Mar - 1 Apr
Villa Dubois Guest House Room 1
Presidential Suite
1 bedroom, iron/ironing board, WiFi, bed sheets

Presidential Suite

Presidential Suite
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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Other property types in Winnetka

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (706)
"We love coming here and we come at least once a year. My only thing is we always get the lake side and this time we did not. Still a nice chicago skyline view but if you can get the lake side it’s gorgeous!"
The price is SAR 475
SAR 668 total
includes taxes & fees
20 Apr - 21 Apr
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (454)
"As advertised. Would stay again. "
The price is SAR 350
SAR 411 total
includes taxes & fees
20 Apr - 21 Apr
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (267)
"It was good. Booking, arrival, and departure were easy. Bed was ok. Everything was clean and smelled nice. Parking was not easy and had to walk quite a distance. I don’t recall seeing that being the case when booking. "
The price is SAR 400
SAR 470 total
includes taxes & fees
21 Apr - 22 Apr
Sonder Market Hall
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.

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: The Villa Toscana: 9 rooms. 12.1 mi (19.5 km) from the heart of Winnetka.Dorothy’s: 7 rooms. 12.1 mi (19.5 km) from the downtown core. Ray’s Bucktown B&B: 11 rooms. Situated 13.2 mi (21.2 km) from the heart of Winnetka. Enjoy the free cooked breakfast and rooftop terrace. The Publishing House B&B: 11 rooms. 16.1 mi (25.9 km) from the heart of downtown. Enjoy the free full breakfast and winery. The Sono Chicago: 7 rooms. Located 14.6 mi (23.5 km) from the core of Winnetka. Enjoy the rooftop terrace and fireplace in the lobby.
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.