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Our top choices for Winnetka bed & breakfast

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (199 reviews)
"Very clean room, friendly staff"
United States
STEVEN
$184 nightly
The price is $208
Apr 19 - Apr 20
Total with taxes and fees
The Publishing House B&B

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (502 reviews)
"Really happy with my choice of this lodging. Centrally located on a quiet street. Very new decor and bedding. Breakfast was good and adequate."
United States
Timothy
$120 nightly
The price is $141
Apr 15 - Apr 16
Total with taxes and fees
The Sono Chicago

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.6 out of 10, Excellent, (112 reviews)
"cozy and close to cool places"
United States
Winter Fox
$74 nightly
The price is $81
Apr 14 - Apr 15
Total with taxes and fees
Dorothy's

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (636 reviews)
"Overall the stay was fantastic looking forward to booking here again in the future "
United States
Rico
$94 nightly
The price is $103
Apr 15 - Apr 16
Total with taxes and fees
The Villa Toscana

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (397 reviews)
"The breakfast alone was worth the trip! Warm, generous, eclectic, this place goes out of their way to welcome their guests. And they’re PET FRIENDLY. "
United States
Peter
$168 nightly
The price is $190
Apr 12 - Apr 13
Total with taxes and fees
Ray's Bucktown B&B

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (499 reviews)
"Wonderful room, very good breakfast!"
United States
James
$184 nightly
The price is $216
Apr 13 - Apr 14
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (116 reviews)
"Everything was perfect. The food was really yummy I would love the salsa recipe. "
United States
Earl
$206 nightly
The price is $242
Apr 20 - Apr 21
Total with taxes and fees
Villa D' Citta

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
$231 nightly
The price is $256
Apr 22 - Apr 23
Total with taxes and fees
Harvey House Bed & Breakfast

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (262 reviews)
"Everything was good."
United States
Michael
$220 nightly
The price is $259
Apr 26 - Apr 27
Total with taxes and fees
Wicker Park Inn
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

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Winnetka B&B information

Number of reviews
2,847
Accommodation
14 B&B
Lowest Price
$81
Highest Price
$259

Frequently asked questions

What is the nightly rate for a B&B in Winnetka?
Prices for B&Bs in Winnetka often vary, but you can find a great deal from $81 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winnetka B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Winnetka?
The best time to book a B&B in Winnetka is during the late spring and summer months, particularly from May to August. This vibrant period welcomes families and travelers seeking a charming coastal escape, with plenty of opportunities for leisurely beach days and outdoor activities. The warm temperatures, typically ranging from the mid-60s to the high 80s Fahrenheit, create an inclusive setting for exploring the picturesque waterfront and enjoying local festivals.

July stands out as the most popular month to visit Winnetka, as residents and visitors alike take advantage of the sun-soaked days and festive community events. During this time, you can indulge in delightful strolls along the beach, savor local cuisine at outdoor eateries, and partake in various cultural activities that reflect the area's lively spirit.

If you're looking for a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, allowing for peaceful walks along the beach and the chance to enjoy the stunning fall foliage in the surrounding parks. It's also a lovely time for exploring local shops and cafes without the summer crowds.
What is the difference between a Winnetka Bed and Breakfast and a hotel?
Every Winnetka B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Winnetka B&Bs.

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