A suburban street with a stone house, a tree, and a clear sky.

Find a Bed and Breakfast in Winnetka from CA $164

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

Our top choices for Winnetka bed & breakfast

A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

1. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (515 reviews)
"I love the location of this B&B. Right across from a beautiful park, walkable to some fabulous restaurants and shops - and the red line is so close! My room was clean, quiet, cutely decorated. The kitchen was well-stocked with breakfast options. My one recommendation would be - I wish the coffee was higher quality! The host was prompt, friendly, and responsive to my needs. I'll be back for sure!"
United States
Kimberly
The price is CA $174
CA $290 total
includes taxes & fees
Sep 13 - Sep 14
House 5863 - Chicago Bed and Breakfast
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (545 reviews)
"Close to some great places to eat locally and about an hour walk to river and central business activities......and a very comfy bed!"
United States
Bronwyn
The price is CA $189
CA $222 total
includes taxes & fees
Aug 31 - Sep 1
The Sono Chicago
A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

3. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (173 reviews)
"Great location, just what we needed."
United States
Stephanie
The price is CA $99
CA $164 total
includes taxes & fees
Sep 2 - Sep 3
Dorothy's
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

4. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (668 reviews)
"Was a nice house the room we stayed in was cozy bed was really comfortable and in walking distance to wrigley field would definitely stay here again"
United States
John
The price is CA $132
CA $211 total
includes taxes & fees
Sep 2 - Sep 3
The Villa Toscana
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

5. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (211 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
The price is CA $297
CA $335 total
includes taxes & fees
Aug 31 - Sep 1
The Publishing House B&B
A bathroom with a glass-tiled wall, a sink, and a shower area.

6. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (413 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is CA $255
CA $288 total
includes taxes & fees
Aug 31 - Sep 1
Ray's Bucktown B&B
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

7. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (132 reviews)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
United States
Mia
The price is CA $375
CA $416 total
includes taxes & fees
Sep 16 - Sep 17
Harvey House Bed & Breakfast
A grand foyer with a wooden staircase, a chandelier, and a large window.

8. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (123 reviews)
"What a pleasant stay, staff was welcoming and wanting to make sure our needs were met with our expectations. Meals were abundant and homemade. Rooms w/bath were clean with abundant towels. We will stay again."
United States
Jeffrey
The price is CA $397
CA $466 total
includes taxes & fees
Sep 2 - Sep 3
Villa D' Citta
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

9. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (281 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is CA $396
CA $465 total
includes taxes & fees
Sep 1 - Sep 2
Wicker Park Inn
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

10. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $659
CA $772 total
includes taxes & fees
Sep 9 - Sep 10
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winnetka Hotel Reviews

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"We absolutely loved this hotel. Location was super great and people were very profesional. 100% recommended."
Claudio 2-night trip
Posted less than an hour ago
L7 Chicago by LOTTE

Find out more about Winnetka

Winnetka B&B information

Number of reviews
1,526
Accommodation
13 B&B
Lowest Price
CA $164
Highest Price
CA $772

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: The Sono Chicago: 7 rooms. 14.6 mi (23.5 km) from the heart of Winnetka. Enjoy the rooftop terrace and fireplace in the lobby. Dorothy's: 7 rooms. 12.1 mi (19.5 km) from the downtown core. 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.Wicker Park Inn: 11 rooms. Located 14.3 mi (23 km) from the core of Winnetka.
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.

Explore a world of travel with Expedia