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Aug 29 - Aug 31
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B&B in Winnetka

The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (467)
"Loved the shared kitchen access! "
The price is NT$4,535
NT$5,324 total
includes taxes & fees
Aug 25 - Aug 26
The Sono Chicago
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
The price is NT$6,502
NT$7,340 total
includes taxes & fees
Sep 7 - Sep 8
The Publishing House B&B
Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (63)
"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."
The price is NT$2,016
NT$3,416 total
includes taxes & fees
Sep 7 - Sep 8
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (590)
"Was a great stay!"
The price is NT$2,781
NT$4,464 total
includes taxes & fees
Aug 24 - Aug 25
The Villa Toscana
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (479)
"Everything was taken care of! A wonderful stay. "
The price is NT$3,967
NT$6,345 total
includes taxes & fees
Aug 20 - Aug 21
House 5863 - Chicago Bed and Breakfast
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
The price is NT$7,899
NT$9,273 total
includes taxes & fees
Aug 19 - Aug 20
Villa D' Citta
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (369)
"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! "
The price is NT$5,377
NT$6,071 total
includes taxes & fees
Aug 20 - Aug 21
Ray's Bucktown B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (251)
"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!"
Wicker Park Inn
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (115)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
The price is NT$7,859
NT$8,997 total
includes taxes & fees
Aug 21 - Aug 22
Harvey House Bed & Breakfast
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Bernell was awesome at check in!! Would definitely recommend this Hotel!!!"
Marco Arturo 1-night trip
Posted 6 hours ago
Crowne Plaza Chicago West Loop by IHG

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: Dorothy's: 7 rooms. 12.1 mi (19.5 km) from the heart of Winnetka.The Villa Toscana: 9 rooms. 12.1 mi (19.5 km) from the downtown core. House 5863 - Chicago Bed and Breakfast: 7 rooms. Situated 9 mi (14.5 km) from the heart of Winnetka. Enjoy the designer toiletries and private yard. Ray's Bucktown B&B: 11 rooms. 13.2 mi (21.2 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. 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 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.