A serene lake with reflections of trees and a cloudy sky.

Find a Bed and Breakfast in Crestwood from CA $233

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Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Crestwood bed & breakfast

A patio with a grill, outdoor seating, and potted plants.

1. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (422 reviews)
"Thank you again for an amazing stay at Rays!"
United States
Lora
The price is CA $267
CA $301 total
includes taxes & fees
Oct 25 - Oct 26
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.

2. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (569 reviews)
"I like that it had a balcony food choice wasn’t my type of style end up ordering food off of site but definitely had all the amenities for you to be ready for the next day. Will be staying again little bit pricey for a short weekend stay but I will definitely be coming back. Very great part of the town hope to own my own own home in this place one day."
United States
Tavarion
The price is CA $198
CA $233 total
includes taxes & fees
Nov 1 - Nov 2
The Sono Chicago
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

3. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (137 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is CA $363
CA $402 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.

4. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (221 reviews)
"We enjoyed amazing breakfast. Everything was great. I enjoyed playing with 2 dogs. It was fun."
Japan
Nobue
The price is CA $341
CA $385 total
includes taxes & fees
Nov 1 - Nov 2
The Publishing House B&B
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

5. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (286 reviews)
"Loved the location"
United States
Mary
The price is CA $371
CA $436 total
includes taxes & fees
Nov 16 - Nov 17
Wicker Park Inn
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a gas stove.

6. Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
The price is CA $472
CA $549 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.
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Top Crestwood Hotel Reviews

River Hotel

River Hotel

8/10 Good
"Great location and friendly staff!"
MARK 1-night trip
Posted 2 hours ago
River Hotel

Find out more about Crestwood

Crestwood B&B information

Number of reviews
1,066
Accommodation
8 B&B
Lowest Price
CA $233
Highest Price
CA $549

Frequently asked questions

Searching for B&Bs in Crestwood?
If you're looking for something a little more offbeat than your standard hotel experience, a bed and breakfast could be a great option for your trip. When you want to explore some of the destination's attractions, Hollywood Park is worth a visit.
Why would you choose a B&B versus a traditional hotel?
B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook, the tiny details are what make bed and breakfasts a home away from home.
What are the best bed and breakfasts in Crestwood?
Below are some well-liked B&Bs in the area: The Sono Chicago: 7 rooms. 18 mi (29 km) from the heart of Crestwood. Enjoy the rooftop terrace and fireplace in the lobby. Ray's Bucktown B&B: 11 rooms. 18.3 mi (29.5 km) from the downtown core. Enjoy the free cooked breakfast and rooftop terrace. Harvey House Bed & Breakfast: 5 rooms. Situated 15.7 mi (25.2 km) from the heart of Crestwood. Enjoy the deli and unique décor. The Publishing House B&B: 11 rooms. 16.1 mi (26 km) from the heart of downtown. Enjoy the free full breakfast and winery. Wicker Park Inn: 11 rooms. Located 17.4 mi (28.1 km) from the core of Crestwood.
When should I stay at a B&B in Crestwood?
When you're dreaming of a escape to Crestwood, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 71°F, while the coldest months are January and February with an average of 31°F. Average annual precipitation for Crestwood is 47 inches.
What is there to do in Crestwood?
Travelers enjoy Crestwood for its restaurants and shopping. If you want to check out some popular attractions in Crestwood, you might enjoy a visit to Hollywood Park. Soldier Field and Gaelic Park are also some sites to visit if you want to see more of the area.
How can I get to and around Crestwood?
You can map out your trip in and around Crestwood ahead of time with these transportation options. Fly into Chicago Midway Airport (MDW), which is located 8.8 mi (14.2 km) away from the heart of the city. You can also search for flights into Chicago O'Hare Intl. Airport (ORD), which is 23.2 mi (37.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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