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Our top choices for Winnetka bed & breakfast

1. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (521 reviews)
"good"
United States
jiantao
$179 nightly
The price is $210
Oct 26 - Oct 27
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast

2. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (191 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
$83 nightly
The price is $91
Nov 2 - Nov 3
Total with taxes and fees
Dorothy's

3. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (682 reviews)
"Nice house set back from the street. Clean room. Nice atmosphere. Would stay again."
United States
John
$116 nightly
The price is $129
Nov 2 - Nov 3
Total with taxes and fees
The Villa Toscana

4. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (420 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
$201 nightly
The price is $227
Oct 13 - Oct 14
Total with taxes and fees
Ray's Bucktown B&B

5. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (565 reviews)
"It was a very comfortable hotel. We loved the free street parking, easy access to public transportation, coffee, breakfast, bottled water, bubbly water and snacks. I will stay here again!"
United States
Christie
$191 nightly
The price is $224
Oct 26 - Oct 27
Total with taxes and fees
The Sono Chicago

6. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (127 reviews)
"Very elegant !"
United States
Hernando
$252 nightly
The price is $296
Oct 26 - Oct 27
Total with taxes and fees
Villa D' Citta

7. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (285 reviews)
"Loved the location"
United States
Mary
$294 nightly
The price is $345
Nov 1 - Nov 2
Total with taxes and fees
Wicker Park Inn

8. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (136 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
$258 nightly
The price is $286
Nov 5 - Nov 6
Total with taxes and fees
Harvey House Bed & Breakfast

9. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (219 reviews)
"Beautiful space"
United States
Mary
$233 nightly
The price is $263
Oct 25 - Oct 26
Total with taxes and fees
The Publishing House B&B

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
$383 nightly
The price is $394
Oct 27 - Oct 28
Total with taxes and fees
Pristine Apartment with Free Street Parking
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
2,791
Accommodation
12 B&B
Lowest Price
$91
Highest Price
$394

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 $91 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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