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Check prices for these dates

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun
In one month
26 Jun - 28 Jun
In two months
24 Jul - 26 Jul

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, (206 reviews)
"Super nice staff and clean rooms. Really neat and unique place to stay. Very relaxing"
United States
Matthew
The price is 6.712.520 ₫
7.577.764 ₫ total
includes taxes & fees
28 Jun - 29 Jun
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, (515 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is 5.662.240 ₫
6.647.206 ₫ total
includes taxes & fees
15 Jun - 16 Jun
The Sono Chicago
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (132 reviews)
"Absolutely perfect stay in Chicago. Everything we needed was there, breakfast was over the top amazing. I LOVE the area and the pizza spot downstairs, this place includes other perks also like BOGO well drink downstairs. Big Gay Sal’s pizza also does room service. I have never felt so at home away from home. 10/10 recommend, HIGHLY recommend"
United States
Jennifer
The price is 3.034.944 ₫
4.484.797 ₫ total
includes taxes & fees
10 Jun - 11 Jun
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, (642 reviews)
"Great location, beautiful charming spot in Chicago that is quiet but somehow in the middle of a big social scene"
United States
Joseph J
The price is 2.789.772 ₫
4.328.353 ₫ total
includes taxes & fees
1 Jun - 2 Jun
The Villa Toscana
Superior Room, 1 King Bed (Room 4) | Egyptian cotton sheets, premium bedding, down duvets

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (504 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 3.634.368 ₫
5.913.485 ₫ total
includes taxes & fees
11 Jun - 12 Jun
House 5863 - Chicago Bed and Breakfast
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (399 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is 4.550.597 ₫
5.137.363 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Ray's Bucktown B&B
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 6.900.032 ₫
7.657.719 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Harvey House Bed & Breakfast
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (265 reviews)
"Very nice place and great location with a lot of restaurants and shops."
United States
Regina
The price is 6.585.580 ₫
7.730.669 ₫ total
includes taxes & fees
23 Jun - 24 Jun
Wicker Park Inn
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (119 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 8.452.793 ₫
9.923.107 ₫ total
includes taxes & fees
10 Jun - 11 Jun
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

Central Loop Hotel

Central Loop Hotel

10/10 Excellent
"We love staying here during the sueños festival! we also appreciate the fact that they give us a discount of the parking lot across from the hotel. Everything is also walking distance from the hotel"
Yamilet 3-night trip
Posted less than an hour ago
Central Loop Hotel

Find out more about Winnetka

Winnetka B&B information

Number of reviews
2,787
Accommodation
9 B&B
Lowest Price
4.328.353 ₫
Highest Price
9.923.107 ₫

Frequently asked questions

Searching for B&Bs in Winnetka?
If you're hoping for something a little different than your standard hotel, a stay at a bed and breakfast could be a great option for your trip. 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 a good option for you?
With attentive service, opportunities to meet other guests and of course a full breakfast to start the day, B&Bs provide a unique setting.
When should I stay at a B&B in Winnetka?
When you're planning your getaway to Winnetka, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Winnetka is 1216 mm.
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 should 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?
You can map out your trip in and around Winnetka ahead of time 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, you can search for flights to Chicago O'Hare International Airport (ORD), which is 12.5 mi (20.2 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

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