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Find a Bed and Breakfast in Winnetka from CA $176

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16

Our top choices for Winnetka bed & breakfast

Private kitchen

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (524 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
The price is CA $242
CA $285 total
includes taxes & fees
Jun 30 - Jul 1
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, (208 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is CA $398
CA $449 total
includes taxes & fees
Jul 19 - Jul 20
The Publishing House B&B
Living area

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (139 reviews)
"lots of clean rooms and clean bathrooms with products you can use. keep in mind however that not every room has its own private bathroom "
United States
Jia
The price is CA $108
CA $176 total
includes taxes & fees
Jul 13 - Jul 14
Dorothy's
Double Room, Private Bathroom (Venetian) | Terrace/patio

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (651 reviews)
"Small, but very convenient! Excellent location!"
Canada
Jeremy
The price is CA $158
CA $242 total
includes taxes & fees
Jul 13 - Jul 14
The Villa Toscana
Spa

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (402 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
The price is CA $321
CA $363 total
includes taxes & fees
Jun 22 - Jun 23
Ray's Bucktown B&B
Beach nearby, white sand

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (507 reviews)
"The place is well run. The communal areas are clean and have what you need. The neighborhood is nice, everyone i took was gorgeous! And the perfect distance from the city."
United States
Joanna
The price is CA $178
CA $296 total
includes taxes & fees
Jun 22 - Jun 23
House 5863 - Chicago Bed and Breakfast
The Garden Suite | Jetted tub

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (127 reviews)
"Spotless room and the best host! Breakfast was warm and delicious."
United States
Christine
The price is CA $382
CA $424 total
includes taxes & fees
Jun 23 - Jun 24
Harvey House Bed & Breakfast
Lobby sitting area

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (120 reviews)
"A fantastic stay yet again. I have stayed here the last few years while attending a conference. All the staff were great and amazing selection of food for breakfast and for late night snacks. I will be back again next year"
United Kingdom
Robert
The price is CA $420
CA $493 total
includes taxes & fees
Jul 13 - Jul 14
Villa D' Citta
Property entrance

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (268 reviews)
"Very nice place and great location with a lot of restaurants and shops."
United States
Regina
The price is CA $378
CA $444 total
includes taxes & fees
Jun 29 - Jun 30
Wicker Park Inn
Fridge, microwave, oven, coffee/tea maker

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $566
CA $667 total
includes taxes & fees
Jun 30 - Jul 1
Pristine Apartment with Free Street Parking
TV

Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Lakeview
The price is CA $1,142
CA $2,184 total
includes taxes & fees
Jul 13 - Jul 14
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

Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

8/10 Good
"Honestly this was an amazing find for a downtown Chicago stay. If you’re super picky about how the room looks and want something modern, this isn’t for you. If you want a great location, helpful staff, affordable rates, and sound proof walls, then this is your place."
Ross 4-night trip
Posted less than an hour ago
Travelodge by Wyndham Downtown Chicago

Find out more about Winnetka

Winnetka B&B information

Number of reviews
2,946
Accommodation
13 B&B
Lowest Price
CA $176
Highest Price
CA $493

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 Sono Chicago: 7 rooms. 14.6 mi (23.5 km) from the downtown core. Enjoy the rooftop terrace and fireplace in the lobby. 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. The Villa Toscana: 9 rooms. 12.1 mi (19.5 km) from the heart of downtown.Ray's Bucktown B&B: 11 rooms. Located 13.2 mi (21.2 km) from the core of Winnetka. Enjoy the free cooked breakfast and rooftop terrace.
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.

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