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Next weekend
Nov 21 - Nov 23
In two weeks
Nov 28 - Nov 30
In one month
Dec 12 - Dec 14
In two months
Jan 9 - Jan 11

B&B in Winnetka

Private kitchen
The Sono Chicago

The Sono Chicago

3.5 star property
Near North Side
10.0 out of 10, Exceptional, (480)
"Great location and hospitality! "
United States
Teresa
$136 nightly
The price is $159
Nov 13 - Nov 14
Total with taxes and fees
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (187)
"This was my first time ever booking at a bed & breakfast and it was amazing!!! The staff were so helpful & great. The breakfast was very delicious. My room was perfect & clean. Everyone was so lovely. Can’t wait to go back!!!"
United States
Jazmine
$212 nightly
The price is $240
Nov 16 - Nov 17
Total with taxes and fees
The Publishing House B&B
Free WiFi, bed sheets
Dorothy's

Dorothy's

3.0 star property
Lakeview
8.4 out of 10, Very Good, (92)
"Halsted is a nice neibourhood. We liked the secondhand shops."
United States
Lisa
$83 nightly
The price is $91
Nov 16 - Nov 17
Total with taxes and fees
Dorothy's
Exterior
The Villa Toscana

The Villa Toscana

2.5 star property
Lakeview
7.8 out of 10, Good, (617)
"We "
United States
Brian
$82 nightly
The price is $89
Nov 17 - Nov 18
Total with taxes and fees
The Villa Toscana
Exterior
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

3.5 star property
Edgewater
9.0 out of 10, Wonderful, (490)
"I loved it was so close to busy Chicago but in the quiet subarbs where it was nice and quiet and felt very safe.The rooms were excellent and well equipped and the kitchen was full of snacks to eat when you wanted and a great selection of drinks. If I ever came to Chicago I would stay here again also the hosts were fantastic "
United Kingdom
Mark
$156 nightly
The price is $183
Nov 13 - Nov 14
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
Property entrance
Wicker Park Inn

Wicker Park Inn

3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"My husband and I loved our stay. The room was beautiful, clean, and comfortable. Being able to stay in a neighborhood inn made our trip to Chicago memorable. We went to the Wicker Park Farmer's Market, ate at local restaurants, hung out at local bars, met cool people, and just enjoyed being part of the city. "
United States
Melissa
$209 nightly
The price is $245
Nov 19 - Nov 20
Total with taxes and fees
Wicker Park Inn
Front of property
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 star property
Bucktown
9.8 out of 10, Exceptional, (381)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
$153 nightly
The price is $173
Nov 13 - Nov 14
Total with taxes and fees
Ray's Bucktown B&B
Lobby sitting area
Villa D' Citta

Villa D' Citta

3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (110)
"Would stay again anytime!!"
United States
Dominic
$206 nightly
The price is $242
Dec 1 - Dec 2
Total with taxes and fees
Villa D' Citta
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

4.0 star property
Oak Park
9.8 out of 10, Exceptional, (119)
"Beautiful home, welcoming host."
United States
scott
$231 nightly
The price is $256
Nov 13 - Nov 14
Total with taxes and fees
Harvey House Bed & Breakfast
5 bedrooms, free WiFi, bed sheets
Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12

Lakeview
$809 nightly
The price is $925
Dec 2 - Dec 3
Total with taxes and fees
Five bedroom - 3 bath - Sleeps 12
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

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Beautiful hotel"
Laura 2-night trip
Posted 3 hours ago
InterContinental Chicago Magnificent Mile by IHG

Find out more about Winnetka

Winnetka B&B information

Number of reviews
2,510
Accommodation
28 B&B
Lowest Price
$89
Highest Price
$925

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 $89 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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