Lodging Image

Find a Bed and Breakfast in Winnetka from CA $120

  • 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
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25
In one month
Nov 6 - Nov 8
In two months
Dec 4 - Dec 6

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, (521 reviews)
"good"
United States
jiantao
The price is CA $180
CA $299 total
includes taxes & fees
Oct 26 - Oct 27
House 5863 - Chicago Bed and Breakfast
A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

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
The price is CA $60
CA $120 total
includes taxes & fees
Nov 2 - Nov 3
Dorothy's
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

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
The price is CA $97
CA $171 total
includes taxes & fees
Nov 2 - Nov 3
The Villa Toscana
A bathroom with a glass-tiled wall, a sink, and a shower area.

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
The price is CA $286
CA $323 total
includes taxes & fees
Oct 13 - Oct 14
Ray's Bucktown B&B
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

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
The price is CA $272
CA $320 total
includes taxes & fees
Oct 26 - Oct 27
The Sono Chicago
A grand foyer with a wooden staircase, a chandelier, and a large window.

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
The price is CA $359
CA $422 total
includes taxes & fees
Oct 26 - Oct 27
Villa D' Citta
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

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
The price is CA $377
CA $443 total
includes taxes & fees
Nov 1 - Nov 2
Wicker Park Inn
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

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
The price is CA $368
CA $408 total
includes taxes & fees
Nov 5 - Nov 6
Harvey House Bed & Breakfast
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

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
The price is CA $325
CA $366 total
includes taxes & fees
Oct 25 - Oct 26
The Publishing House B&B
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 $479
CA $563 total
includes taxes & fees
Oct 27 - Oct 28
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

8/10 Good
"Hotel was unique and enjoyed the location. Room was very basic but functional. Lobby was very welcoming."
Lindsey Marie 3-night trip
Posted 6 hours ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Winnetka

Winnetka B&B information

Number of reviews
2,791
Accommodation
12 B&B
Lowest Price
CA $120
Highest Price
CA $563

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. The Villa Toscana: 9 rooms. 12.1 mi (19.5 km) from the downtown core. Dorothy's: 7 rooms. Situated 12.1 mi (19.5 km) from the heart of Winnetka. House 5863 - Chicago Bed and Breakfast: 7 rooms. 9 mi (14.5 km) from the heart of downtown. Enjoy the designer toiletries and private yard. 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 check out Elder Lane Beach if you have time 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