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Compare 16 B&B in Crestwood with updated reviews, rates, and availability.

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (356)
"Breakfast was great, the staff was kind, and it was a pleasant surprise. "
The price is AED 678
AED 766 total
includes taxes & fees
4 Jun - 5 Jun
Ray's Bucktown B&B

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (457)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 520
AED 611 total
includes taxes & fees
4 Jun - 5 Jun
The Sono Chicago

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (176)
"Incredible service, amazing breakfast and gorgeous rooms."
The price is AED 619
AED 699 total
includes taxes & fees
29 Jun - 30 Jun
The Publishing House B&B

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (244)
"Gorgeous, clean, lovely breakfast, accommodating staff"
The price is AED 1,094
AED 1,284 total
includes taxes & fees
11 Jun - 12 Jun
Wicker Park Inn

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
The price is AED 962
AED 1,102 total
includes taxes & fees
9 Jun - 10 Jun
Harvey House Bed & Breakfast

Dubois Guest House Room 202

The price is AED 620
AED 1,050 total
includes taxes & fees
12 Jun - 13 Jun
Dubois Guest House Room 202

Dubois Guest House Room 101

The price is AED 620
AED 1,050 total
includes taxes & fees
12 Jun - 13 Jun
Dubois Guest House Room 101

Villa Dubois Guest Room 6

The price is AED 496
AED 877 total
includes taxes & fees
8 Jun - 9 Jun
Villa Dubois Guest Room 6

Villa Dubois Guest House Room 5

The price is AED 496
AED 885 total
includes taxes & fees
17 Jun - 18 Jun
Villa Dubois Guest House Room 5

Dubois Guest House Room 203

The price is AED 744
AED 1,224 total
includes taxes & fees
8 Jun - 9 Jun
Dubois Guest House Room 203

Villa Dubois Guest House Room 2

The price is AED 620
AED 1,058 total
includes taxes & fees
7 Jun - 8 Jun
Villa Dubois Guest House Room 2

Rustic cottage-style condo within walking distance to downtown Homewood

8.8 out of 10, Excellent, (10)
"Great location, close to Credit Union 1 amphlitheater and walking distance to a good breakfast spot. Quiet neighborhood and clean apartment. Perfect space for a girls’ getaway."
Rustic cottage-style condo within walking distance to downtown Homewood

Villa Dubois Guest House Room 1

The price is AED 744
AED 1,224 total
includes taxes & fees
8 Jun - 9 Jun
Villa Dubois Guest House Room 1

Adorable bed & breakfast in Chicago2222

Adorable bed & breakfast in Chicago2222
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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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: Ray’s Bucktown B&B: 11 rooms. 18.3 mi (29.5 km) from the heart of Crestwood. Enjoy the free cooked breakfast and rooftop terrace. The Sono Chicago: 7 rooms. 18 mi (29 km) from the downtown core. Enjoy the rooftop terrace and fireplace in the lobby. The Publishing House B&B: 11 rooms. Situated 16.1 mi (26 km) from the heart of Crestwood. Enjoy the free full breakfast and winery. Wicker Park Inn: 11 rooms. 17.4 mi (28.1 km) from the heart of downtown.Harvey House Bed & Breakfast: 5 rooms. Located 15.7 mi (25.3 km) from the core of Crestwood. Enjoy the deli and unique décor.
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.