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

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (24)
"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 AED 116
AED 264 total
includes taxes & fees
27 Mar - 28 Mar
Dorothy's

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 AED 569
AED 667 total
includes taxes & fees
24 Mar - 25 Mar
The Sono Chicago

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 AED 639
AED 721 total
includes taxes & fees
24 Mar - 25 Mar
Ray's Bucktown B&B

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (241)
"The Wicker Park Inn was located close to many transportation options. The breakfast room was bright and sunny with good light breakfast options."
The price is AED 798
AED 937 total
includes taxes & fees
24 Mar - 25 Mar
Wicker Park Inn

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 AED 756
AED 888 total
includes taxes & fees
2 Apr - 3 Apr
Villa D' Citta

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 AED 848
AED 942 total
includes taxes & fees
24 Mar - 25 Mar
Harvey House Bed & Breakfast

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 528
AED 924 total
includes taxes & fees
24 Mar - 25 Mar
Wrigleyville Suites Room 1

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 656
AED 988 total
includes taxes & fees
24 Mar - 25 Mar
House 5863 - Chicago Bed and Breakfast

Villa Dubois Guest Room 6

The price is AED 273
AED 593 total
includes taxes & fees
24 Mar - 25 Mar
Villa Dubois Guest Room 6

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 5

The price is AED 273
AED 593 total
includes taxes & fees
24 Mar - 25 Mar
Villa Dubois Guest House Room 5

Room in Town house Rogers Park

Room in Town house Rogers Park

Villa Dubois Guest House Room 2

The price is AED 302
AED 629 total
includes taxes & fees
24 Mar - 25 Mar
Villa Dubois Guest House Room 2

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
The price is AED 528
AED 924 total
includes taxes & fees
24 Mar - 25 Mar
Wrigleyville Suites Room 2

Wrigleyville Suites Room 3

2.0 star property
The price is AED 528
AED 924 total
includes taxes & fees
24 Mar - 25 Mar
Wrigleyville Suites Room 3

Villa Dubois Guest House Room 1

The price is AED 362
AED 700 total
includes taxes & fees
24 Mar - 25 Mar
Villa Dubois Guest House Room 1

Presidential Suite

Presidential Suite

Adorable bed & breakfast in Chicago2222

Adorable bed & breakfast in Chicago2222
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, (702)
"Friendly staff "
The price is AED 465
AED 654 total
includes taxes & fees
24 Mar - 25 Mar
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (451)
"Nice property, big clean rooms "
The price is AED 343
AED 402 total
includes taxes & fees
20 Apr - 21 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (267)
"Appartement spacieux, super fonctionnel, lit et divan lit très confortables. Très bien situé, à 2 min du metro dans un quartier hyper sécuritaire."
The price is AED 392
AED 460 total
includes taxes & fees
16 Apr - 17 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. The Publishing House B&B: 11 rooms. Situated 16.1 mi (25.9 km) from the heart of Winnetka. Enjoy the free full breakfast and winery. 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.