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

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (507)
"Complimentary breakfast was far beyond "continental", it was handmade from scratch and incredible! That's what really stood out. Otherwise my stay was also great, everything the listing claimed to be."
The price is AED 195
AED 375 total
includes taxes & fees
12 Jan - 13 January 2025
The Villa Toscana

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (11)
"Love the coziness of the location and th area is nice and safe "
The price is AED 135
AED 287 total
includes taxes & fees
6 Jan - 7 January 2025
Dorothy's

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (337)
"I chose Rays s it was conveniently located near my client. A B&B would never be my choice for a business trip but I feel lucky I found this place. Great accommodations. Felt like a mini vacation. I’m returning when I can. "
The price is AED 547
AED 617 total
includes taxes & fees
1 Jan - 2 January 2025
Ray's Bucktown B&B

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (440)
"The Sono Chicago was a dream! Staff & Owner were friendly, accommodating, and gave great advice for dining & entertainment. Our bed was comfortable, bathroom was luxurious, and the balcony was fun for morning coffee. There is a nice rooftop area with seating and fire tables where you can relax/socialize. Parking was convenient and FREE! I def recommend The Sono Chicago!"
The price is AED 555
AED 652 total
includes taxes & fees
29 Dec - 30 Dec
The Sono Chicago

The Publishing House B&B

3.5 star property
10.0 out of 10, Exceptional, (163)
"We absolutely loved our stay. The breakfast was amazing and the staff were great. We can’t wait to come back."
The price is AED 583
AED 658 total
includes taxes & fees
23 Jan - 24 January 2025
The Publishing House B&B

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 AED 848
AED 942 total
includes taxes & fees
30 Dec - 31 Dec
Harvey House Bed & Breakfast

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 AED 672
AED 788 total
includes taxes & fees
5 Jan - 6 January 2025
Wicker Park Inn

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!"
The price is AED 520
AED 820 total
includes taxes & fees
1 Jan - 2 January 2025
House 5863 - Chicago Bed and Breakfast

Villa D' Citta

3.5 star property
9.2 out of 10, Wonderful, (98)
"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 AED 756
AED 888 total
includes taxes & fees
6 Jan - 7 January 2025
Villa D' Citta

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 AED 275
AED 587 total
includes taxes & fees
25 Dec - 26 Dec
Wrigleyville Suites Room 1

Villa Dubois Guest Room 6

The price is AED 248
AED 555 total
includes taxes & fees
25 Dec - 26 Dec
Villa Dubois Guest Room 6

Villa Dubois Guest House Room 5

The price is AED 248
AED 555 total
includes taxes & fees
25 Dec - 26 Dec
Villa Dubois Guest House Room 5

Villa Dubois Guest House Room 2

The price is AED 248
AED 555 total
includes taxes & fees
25 Dec - 26 Dec
Villa Dubois Guest House Room 2

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

The price is AED 248
AED 555 total
includes taxes & fees
25 Dec - 26 Dec
Villa Dubois Guest House Room 4

Room in Town house Rogers Park

Room in Town house Rogers Park

Charming 3 bedrooms Apartment at the Medical District

2.0 star property
10.0 out of 10, Exceptional, (3)
"The entire experience associated with this VRBO rental was excellent. The location was great - 15 mins to downtown McCormack Center. The street had plenty of parking and very quiet at night. There are plenty of restaurants within walking distance. The rental was very clean and stocked with the necessary items you would need during a stay. The check in process was easy and the host was quick to respond to text messages. Unit provided parking. I would rent this unit again."
Charming 3 bedrooms Apartment at the Medical District

Four bedroom apartment

The price is AED 463
AED 1,193 total
includes taxes & fees
6 Jan - 7 January 2025
Four bedroom apartment

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is AED 275
AED 587 total
includes taxes & fees
25 Dec - 26 Dec
Wrigleyville Suites Room 2

Wrigleyville Suites Room 3

2.0 star property
The price is AED 275
AED 587 total
includes taxes & fees
25 Dec - 26 Dec
Wrigleyville Suites Room 3
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

4.0 star property
9.2 out of 10, Wonderful, (626)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is AED 403
AED 581 total
includes taxes & fees
25 Dec - 26 Dec
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (342)
"The property location was great. The room was very spacious. The only knock was there was not a tv in the bedroom."
Kasa Magnificent Mile Chicago

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (407)
"The stay was great."
The price is AED 456
AED 535 total
includes taxes & fees
13 Jan - 14 January 2025
Sonder South Wabash
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.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.