Find a Bed and Breakfast in Winnetka from CA $101

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Browse Select Winnetka B&B

Relax in this stylish living area with a large sofa, glass coffee table, and patterned rug.

"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."

CA $167 total

includes taxes & fees

Aug 13 - Aug 14

Stroll through this charming neighborhood to a traditional two-story house with a cozy front porch and balcony.

"Was a great stay!"

CA $188 total

includes taxes & fees

Aug 11 - Aug 12

Experience the charm of this historic building, featuring a welcoming entrance, lush garden, and large windows offering views of the surrounding area.

"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "

CA $286 total

includes taxes & fees

Aug 10 - Aug 11

Stunning corner building with a brick facade and large windows, surrounded by lush greenery.

"Everything was taken care of! A wonderful stay. "

CA $291 total

includes taxes & fees

Aug 11 - Aug 12

Staircase leads to an upper level with potted plants and decorative shelves.

"What a lovely place to stay. This bnb was perect!"

CA $246 total

includes taxes & fees

Sep 4 - Sep 5

Welcome to The Wicker Park Inn, a charming urban B&B located at 1329 N. Wicker Park.

"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"

CA $320 total

includes taxes & fees

Sep 2 - Sep 3

Enter a classic space with a traditional feel, featuring a dresser, lamp, and ornate rug.

"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"

CA $412 total

includes taxes & fees

Aug 11 - Aug 12

Enjoy cooking in this well-equipped kitchen with a central island, sink, and oven.

"Excellent location. Beautiful property, extremely clean."

CA $300 total

includes taxes & fees

Aug 10 - Aug 11

Kitchen features a gas range, double sink, and dishwasher.

"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"

Step into a grand lobby with a classic staircase, elegant seating area, and beautiful views.

"Would stay again anytime!!"

CA $369 total

includes taxes & fees

Aug 13 - Aug 14

CA $327 total

includes taxes & fees

Aug 10 - Aug 11

"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...