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Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
In two weeks
7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

Compare 23 B&B in Winnetka with updated reviews, rates, and availability.

The Villa Toscana
Lounge

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (519)
"Thank you for my trip"
The price is SAR 203
SAR 388 total
includes taxes & fees
27 Jan - 28 Jan
The Villa Toscana
Dorothy's
Room

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (17)
"How nice it was and how close it was"
The price is SAR 131
SAR 285 total
includes taxes & fees
24 Jan - 25 Jan
Dorothy's
The Sono Chicago
Room

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (443)
"Likely the best hotel experience we’ve had. Nice place in a good location. The breakfast was a great perk. Felt like we stumbled on a hidden gem spot. "
The price is SAR 509
SAR 597 total
includes taxes & fees
25 Jan - 26 Jan
The Sono Chicago
The Publishing House B&B
Fireplace

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (166)
"Was surprisingly excellent "
The price is SAR 567
SAR 640 total
includes taxes & fees
6 Feb - 7 Feb
The Publishing House B&B
Wicker Park Inn
Room

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (238)
"This was the second time that I stayed at this property. The rooms are so beautiful and all the people are so friendly. I love the area and easy access to parking, would definitely stay here again and again! :)"
The price is SAR 686
SAR 805 total
includes taxes & fees
30 Jan - 31 Jan
Wicker Park Inn
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (340)
"This B&B is a gem. Loved it. It’s like staying in someone’s huge, comfortable home with a fabulous hostess. Plenty of parking, creative decor, and the huge made to order breakfast is fabulous. They have snacks, homemade baked goods and all kinds of drinks in the kitchen. They serve breakfast until 11 for late risers. Laundry, sauna, steam room. Will definitely stay again."
The price is SAR 652
SAR 736 total
includes taxes & fees
24 Jan - 25 Jan
Ray's Bucktown B&B
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
Harvey House Bed & Breakfast
Interior

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (107)
"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
27 Jan - 28 Jan
Harvey House Bed & Breakfast
Villa D' Citta
Front of property

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (99)
"Perfection "
The price is SAR 772
SAR 907 total
includes taxes & fees
27 Jan - 28 Jan
Villa D' Citta
Wrigleyville Suites Room 1
Bedroom with a queen-sized bed, patterned wallpaper, two windows with blinds, and a geometric rug on the floor.

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 302
SAR 625 total
includes taxes & fees
24 Jan - 25 Jan
Wrigleyville Suites Room 1
Villa Dubois Guest Room 6
A cozy bedroom with a patterned wallpaper wall, a large mirror, a queen size bed with grey linens, a bedside table with a lamp and towels, and a window with white curtains.

Villa Dubois Guest Room 6

Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
A cozy and modern bedroom with brownish paper wall, a comfortable queen size bed, a large window with natural light, and stylish artwork.

Villa Dubois Guest House Room 5

Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
A simply furnished room with a plush armchair, a wooden table with and a framed painting on a blue ash paper wall.

Villa Dubois Guest House Room 2

The price is SAR 253
SAR 566 total
includes taxes & fees
27 Jan - 28 Jan
Villa Dubois Guest House Room 2
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Dining Room

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 4
A cozy and stylish bedroom with a comfortable bed, a patterned armchair, and a unique wall decoration.

Villa Dubois Guest House Room 4

Villa Dubois Guest House Room 4
Charming 3 bedrooms Apartment at the Medical District
Living area

Charming 3 bedrooms Apartment at the Medical District

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great host, great place, great location."
Charming 3 bedrooms Apartment at the Medical District
Room in Town house Rogers Park
Living area

Room in Town house Rogers Park

Room in Town house Rogers Park
Wrigleyville Suites Room 2
Bedroom with a metal bunk bed, patterned wallpaper, a wooden chair, and a window with blinds.

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is SAR 302
SAR 625 total
includes taxes & fees
25 Jan - 26 Jan
Wrigleyville Suites Room 2
Wrigleyville Suites Room 3
Cozy bedroom with a grey patterned wallpaper wall, a queen sized bed with grey linens and white towels, two bedside tables with lamps, and a window with natural light.

Wrigleyville Suites Room 3

2.0 star property
The price is SAR 302
SAR 625 total
includes taxes & fees
24 Jan - 25 Jan
Wrigleyville Suites Room 3
Villa Dubois Guest House Room 1
King size bed, grey with blue wall paper design

Villa Dubois Guest House Room 1

Villa Dubois Guest House Room 1
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
Pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (661)
"We stayed at Sentral after a trip to the Shedd with the kids. We had a great day and evening in the city and when we finally got to our room, we couldn't believe it! It was so spacious, we could have stayed for a week. Full kitchen, stocked with appliances, utensils, plates and glasses. Two full baths, two bedrooms and more closet space than we could have possibly used. Location was close to everything you'd need. We'll definitely be back."
The price is SAR 411
SAR 593 total
includes taxes & fees
27 Jan - 28 Jan
Sentral Michigan Avenue
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (419)
"Great place to spend a few days. "
The price is SAR 412
SAR 484 total
includes taxes & fees
28 Jan - 29 Jan
Sonder South Wabash
Sonder Market Hall
Living area

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (245)
"New. Modern. Cozy.Clean & quiet place. Will book it again!"
The price is SAR 223
SAR 261 total
includes taxes & fees
17 Feb - 18 Feb
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 want to explore some attractions in town, Lake Michigan and Chocolate Box are worth a stop.
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.The Sono Chicago: 7 rooms. 14.6 mi (23.5 km) from the downtown core. Enjoy the rooftop terrace and fireplace in the lobby. Dorothy’s: 7 rooms. Situated 12.1 mi (19.5 km) from the heart of Winnetka. 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. 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.