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Compare 13 B&B in Winnetka with updated reviews, rates, and availability.

The Villa Toscana
2.5 star property
7.6 out of 10, Good, (430)
"GREAT stay and location! Very COZY and near LOTS of shops, restaurants, clubs, CTA, etc! Only thing is it's HUMANLESS Check-in/Out! All Communication/Codes are sent via email or text!"
The price is $37
$84 total
includes taxes & fees
Jun 6 - Jun 7
The Villa Toscana
Old Chicago Inn
2.0 star property
7.4 out of 10, Good, (731)
"Everyone was helpful from the outset. I appreciated being able to drop off our luggage when we arrived early, as the staff were still getting our room ready. We ate at a few restaurants in the area and the Belmont L station was a few steps away, which was very convenient."
Old Chicago Inn
Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (219)
"We really enjoyed our stay at the Wicker Park Inn. Nestled in a quiet street with many trees and birds it’s very peaceful and relaxing. There is a tram that runs behind the building periodically but it’s not a harsh sound, kind of pleasant to be honest, like a wave or roll of thunder that comes and goes. The Inn itself is spotless, comfortable and well appointed with great attention to detail. It’s obvious the owners understand the needs of their guests. The location is perfect, just a block...
The price is $252
$311 total
includes taxes & fees
Jul 1 - Jul 2
Wicker Park Inn
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Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (291)
"This is a great property to stay at while in Chicago. Many bars and restaurants nearby as well as easy to get to public transportation. Staff and breakfast are incredible. "
The price is $180
$203 total
includes taxes & fees
Jun 24 - Jun 25
Ray's Bucktown B&B
House 5863 - Chicago Bed and Breakfast
3.5 star property
9.0 out of 10, Wonderful, (463)
"Great traditional bnb. Friendly staff. Great patio. Comfortable and clean"
The price is $158
$243 total
includes taxes & fees
Jun 11 - Jun 12
House 5863 - Chicago Bed and Breakfast
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (419)
"The Sono is a terrific property and highly recommended. Rooms are lovely, the common areas are outstanding, we enjoyed hanging out with our traveling group along with a frig stocked with waters. Breakfast in the morning is a really nice feature. The only drawback is the location in a largely residential area. Yet it is an easy walk or Uber downtown. I would highly recommend the property and special thanks to Addie. "
The price is $182
$214 total
includes taxes & fees
Jun 17 - Jun 18
The Sono Chicago
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (149)
"Unique and bespoke style. Great west loop location "
The price is $232
$262 total
includes taxes & fees
Jun 16 - Jun 17
The Publishing House B&B
Villa D' Citta
3.5 star property
9.4 out of 10, Exceptional, (81)
"Very nice place to stay in the Lincoln Park area. Comfortable rooms and wonderful amenities."
The price is $229
$269 total
includes taxes & fees
Jun 24 - Jun 25
Villa D' Citta
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
9.8 out of 10, Exceptional, (122)
"Nice. clean place in a convenient location to get in and out of Wrigley while avoiding the crowds."
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (94)
"This was the first time I've stayed at a Bed and Breakfast, and it was a positive experience. Our room (the Oak Park Suite) was spacious and comfortable, though the pillows on the bed were very flat. Parking was easy, the host/owner was hospitable, and it's an easy walk both to the Metra and to the shops of Oak Park."
The price is $262
$291 total
includes taxes & fees
Jun 10 - Jun 11
Harvey House Bed & Breakfast
9 bed 10 bath in Lakeview
9 bed 10 bath in Lakeview
Charming 3rd Floor Penthouse in B&B
Charming 3rd Floor Penthouse in B&B
Presidential Suite
Presidential Suite
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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.

Other property types in Winnetka

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (426)
"Property was beautiful and well kept. Room was comfortable and felt like home. The pool was disappointing and much smaller than it appears. Communication during check in and valets could be better. "
The price is $199
$263 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, (94)
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is $97
$114 total
includes taxes & fees
Jun 30 - Jul 1
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (309)
"Sonder rocks!"
The price is $187
$220 total
includes taxes & fees
Jun 9 - Jun 10
Sonder South Wabash
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.

Winnetka B&B information

Number of reviews
2,427
Accommodation
13 B&B
Lowest Price
$37
Highest Price
$262

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: Old Chicago Inn: 10 rooms. 12.3 mi (19.8 km) from the heart of Winnetka. Enjoy the free full breakfast and fireplace in the lobby. The Villa Toscana: 9 rooms. 12.1 mi (19.5 km) from the downtown core. Ray’s Bucktown B&B: 11 rooms. Situated 13.2 mi (21.2 km) from the heart of Winnetka. Enjoy the free cooked breakfast and rooftop terrace. Wicker Park Inn: 11 rooms. 14.3 mi (23 km) from the heart of downtown.House 5863 - Chicago Bed and Breakfast: 7 rooms. Located 9 mi (14.5 km) from the core of Winnetka. Enjoy the designer toiletries and private yard.
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?
If you’re looking to find something to do during your travels, you might consider checking out Home Alone House and Chocolate Box. You might put Lake Michigan and Maple Street 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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