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B&B in Winnetka

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (59)
"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."
$116 nightly
The price is $130
Aug 12 - Aug 13
Total includes taxes and fees
Dorothy's

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (588)
"Was a great stay!"
$128 nightly
The price is $144
Aug 12 - Aug 13
Total includes taxes and fees
The Villa Toscana

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! "
$206 nightly
The price is $233
Aug 10 - Aug 11
Total includes taxes and fees
Ray's Bucktown B&B

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (476)
"Everything was taken care of! A wonderful stay. "
$180 nightly
The price is $212
Aug 11 - Aug 12
Total includes taxes and fees
House 5863 - Chicago Bed and Breakfast

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!"
$164 nightly
The price is $186
Sep 4 - Sep 5
Total includes taxes and fees
The Publishing House B&B

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (250)
"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!"
$220 nightly
The price is $259
Sep 2 - Sep 3
Total includes taxes and fees
Wicker Park Inn

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (114)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
$262 nightly
The price is $300
Aug 11 - Aug 12
Total includes taxes and fees
Harvey House Bed & Breakfast

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (465)
"Excellent location. Beautiful property, extremely clean."
$196 nightly
The price is $230
Aug 12 - Aug 13
Total includes taxes and fees
The Sono Chicago

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (143)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
$229 nightly
The price is $269
Aug 11 - Aug 12
Total includes taxes and fees
Villa D' Citta

Villa Dubois Guest Room 6

$206 nightly
The price is $238
Aug 10 - Aug 11
Total includes taxes and fees
Villa Dubois Guest Room 6

Wrigleyville Suites Room 1

2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
Wrigleyville Suites Room 1

Wrigleyville Suites Room 3

2.0 star property
Wrigleyville Suites Room 3

Villa Dubois Guest House Room 5

$211 nightly
The price is $244
Aug 8 - Aug 9
Total includes taxes and fees
Villa Dubois Guest House Room 5

Villa Dubois Guest House Room 2

$249 nightly
The price is $290
Aug 16 - Aug 17
Total includes taxes and fees
Villa Dubois Guest House Room 2

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
Wrigleyville Suites Room 2

Villa Dubois Guest House Room 1

$284 nightly
The price is $331
Aug 10 - Aug 11
Total includes taxes and fees
Villa Dubois Guest House Room 1

Five bedroom - 3 bath - Sleeps 12

$1,277 nightly
The price is $1,478
Aug 12 - Aug 13
Total includes taxes and fees
Five bedroom - 3 bath - Sleeps 12

Wrigleyville Suites Room 5

$318 nightly
The price is $373
Aug 10 - Aug 11
Total includes taxes and fees
Wrigleyville Suites Room 5

Wrigleyville Suites Room 6

$318 nightly
The price is $373
Aug 10 - Aug 11
Total includes taxes and fees
Wrigleyville Suites Room 6
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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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 $130 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.