Find a Bed and Breakfast in Winnetka from CA $122

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Check prices for these dates

Next weekend
May 1 - May 3
In two weeks
May 8 - May 10
In one month
May 22 - May 24
In two months
Jun 19 - Jun 21

Our top choices for Winnetka bed & breakfast

Staircase

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (202 reviews)
"Loved this place - little gem that you'd never notice from the street. Great breakfast and the beds were good too."
United States
Noah
The price is CA $306
CA $345 total
includes taxes & fees
May 10 - May 11
The Publishing House B&B
Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (504 reviews)
"Excelente place, close to restaurants and very comfortable and clean. "
United States
Juan
The price is CA $163
CA $191 total
includes taxes & fees
Apr 27 - Apr 28
The Sono Chicago
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (115 reviews)
"First time at Dorothy's but I've stayed at her sister location so I know the owner/management and what to expect. Great location and the building is kept up very well. My only non happy comment was no dresser in this room. Its ok since this visit was just me. Being able to use a full kitchen and store food in the refrigerator is a major plus"
United States
Robert
The price is CA $63
CA $122 total
includes taxes & fees
Apr 27 - Apr 28
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (636 reviews)
"The Villa Toscana is in a great location!"
United States
Sophie
The price is CA $78
CA $146 total
includes taxes & fees
Apr 26 - Apr 27
The Villa Toscana
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (397 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is CA $223
CA $252 total
includes taxes & fees
Apr 26 - Apr 27
Ray's Bucktown B&B
Courtyard

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (501 reviews)
"Great place and neighborhood to stay. Walked everywhere, including to the beach. The room had everything I needed. Fresh coffee and breakfast items steps from my room in the morning. Will stay again. "
United States
Cheryl
The price is CA $179
CA $295 total
includes taxes & fees
Apr 29 - Apr 30
House 5863 - Chicago Bed and Breakfast
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (262 reviews)
"Adorable space, comfortable bed, friendly staff"
United States
Marie
The price is CA $259
CA $304 total
includes taxes & fees
Apr 26 - Apr 27
Wicker Park Inn
Property entrance

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (124 reviews)
"The Property was beautiful! When we walked in, the first utterance out of our mouths was "Wow!" Street parking was easy. The room "The Chalet" that we stayed in was spacious with many amenities and was spotless. The bed was very comfortable as well! And being on the third story, we got our stair steps in for our trip! Haha."
United States
Timothy
The price is CA $316
CA $350 total
includes taxes & fees
Apr 27 - Apr 28
Harvey House Bed & Breakfast
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (118 reviews)
"Gina and staff were warm and friendly. When our toilet clogged, we got upgraded. When we needed a delayed checkout, they accommodated. We had a fire for a cold night and got delicious eggs and crispy bacon for breakfast. Highly recommend for those lovers of all things Italian. "
United States
Dana
The price is CA $313
CA $367 total
includes taxes & fees
Apr 27 - Apr 28
Villa D' Citta
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

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

4/10 Poor
"This property lacked cleanliness. The rugs in the rooms were nasty. I don’t know if they have ever cleaned them. They only do housekeeping every other day, and if you ask them to clean it on a day it isn’t scheduled. They give you resonses, in a nice way that it’s not your day. You have to be to the point if you want it done regularly. They also don’t give you new towels on your off day, unless you ask. Clean up on your day consist of fresh towels, bed made, change the trash will try and tell you when you last had house keeping. There is a $70 parking fee if you decide to rent a car. That wouldn’t have been an issue if we were told that there was a charge to park when we asked about parking. We were just told that they do have parking. Also if you park it has to be for the whole time tha you are there, which we weren’t told that as welll. If you park without the hotel validating your parking, it could be more expensive. in the beginning, but no one told us that, and we asked It is not the hotel’s garage."
Shauna Lorraine 6-night trip
Posted less than an hour ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Find out more about Winnetka

Winnetka B&B information

Number of reviews
2,859
Accommodation
11 B&B
Lowest Price
CA $122
Highest Price
CA $367

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. If you're hoping to spend some time walking along the water in Winnetka, Elder Lane Beach is worth a 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.The Sono Chicago: 7 rooms. 14.6 mi (23.5 km) from the downtown core. Enjoy the rooftop terrace and fireplace in the lobby. The Villa Toscana: 9 rooms. Situated 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 heart of downtown. Enjoy the designer toiletries and private yard. The Publishing House B&B: 11 rooms. Located 16.1 mi (25.9 km) from the core of Winnetka. Enjoy the free full breakfast and winery.
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 Elder Lane Beach are some notable spots. You might put Chocolate Box and Maple Street 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.

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