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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

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

The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (449)
"This bed and breakfast was an absolutely breathtaking gem that surpassed every expectation we had, delivering an experience that went well beyond what the photographs could capture. From the moment we arrived, we were struck by the stunning beauty of the place, which seemed to offer everything one could possibly desire in a cozy getaway. The owners were the epitome of hospitality—warm, welcoming, and genuinely sweet—always ready to lend a hand with anything we needed, whether it was local...
The price is AED 538
AED 631 total
includes taxes & fees
23 Mar - 24 Mar
The Sono Chicago
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (343)
"This used to be Ray's photo studio, because he was a professional photographer. That probably wouldn't matter to most people, but I am also a professional photographer and I really enjoyed talking with Ray about birds and his travels. I really appreciated the indoor parking, and the breakfasts were very large. The staff was very friendly and helpful in explaining everything that we had access to in the building. It would be a great stop for kids because of all the games available. Loved...
The price is AED 639
AED 721 total
includes taxes & fees
24 Mar - 25 Mar
Ray's Bucktown B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (241)
"The Wicker Park Inn was located close to many transportation options. The breakfast room was bright and sunny with good light breakfast options."
The price is AED 798
AED 937 total
includes taxes & fees
23 Mar - 24 Mar
Wicker Park Inn
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (109)
"This is a beautiful little stay that feels like a walk back in time with a wonderful host Beth and delicious options for food and activities! We will be back "
The price is AED 848
AED 942 total
includes taxes & fees
24 Mar - 25 Mar
Harvey House Bed & Breakfast
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is AED 273
AED 593 total
includes taxes & fees
23 Mar - 24 Mar
Dubois Guest House Room 101
Dubois Guest House Room 201
Fridge, microwave, oven, stovetop

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
The price is AED 307
AED 635 total
includes taxes & fees
24 Mar - 25 Mar
Dubois Guest House Room 201
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 273
AED 593 total
includes taxes & fees
23 Mar - 24 Mar
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

The price is AED 273
AED 593 total
includes taxes & fees
23 Mar - 24 Mar
Villa Dubois Guest House Room 5
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

The price is AED 302
AED 629 total
includes taxes & fees
23 Mar - 24 Mar
Dubois Guest House Room 202
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is AED 362
AED 700 total
includes taxes & fees
23 Mar - 24 Mar
Dubois Guest House Room 203
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is AED 302
AED 629 total
includes taxes & fees
23 Mar - 24 Mar
Villa Dubois Guest House Room 2
Rustic cottage-style condo within walking distance to downtown Homewood
Fridge, microwave, coffee/tea maker, toaster

Rustic cottage-style condo within walking distance to downtown Homewood

8.8 out of 10, Excellent, (10)
"The property was clean and attractive. It’s located in downtown Homewood with an easy walking distance of restaurants and shopping. The door takes a little bit of time to figure out. You need to wait time before you can hear it lock. Some of the door knobs were coming loose. A few of the ceiling fixtures were coming loose as well. It was a safe, clean, convenient, affordable option. I appreciated that the host answered my questions right away. Guest should know that there is parking available in...
Rustic cottage-style condo within walking distance to downtown Homewood
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is AED 362
AED 700 total
includes taxes & fees
23 Mar - 24 Mar
Villa Dubois Guest House Room 1
Adorable bed & breakfast in Chicago2222
Pool

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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Other property types in Crestwood

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (701)
"Friendly staff "
The price is AED 496
AED 691 total
includes taxes & fees
23 Mar - 24 Mar
Sentral Michigan Avenue
Sonder South Wabash
Superior Apartment, 1 Bedroom, Balcony, City View | Living area | 36-inch flat-screen TV with digital channels, TV

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (451)
"Nice property, big clean rooms "
The price is AED 343
AED 403 total
includes taxes & fees
16 Apr - 17 Apr
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (267)
"Appartement spacieux, super fonctionnel, lit et divan lit très confortables. Très bien situé, à 2 min du metro dans un quartier hyper sécuritaire."
The price is AED 392
AED 460 total
includes taxes & fees
14 Apr - 15 Apr
Sonder Market Hall
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.

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 Publishing House B&B: 11 rooms. 16.1 mi (26 km) from the heart of Crestwood. Enjoy the free full breakfast and winery. The Sono Chicago: 7 rooms. 18 mi (29 km) from the downtown core. Enjoy the rooftop terrace and fireplace in the lobby. Wicker Park Inn: 11 rooms. Situated 17.4 mi (28.1 km) from the heart of Crestwood. Ray’s Bucktown B&B: 11 rooms. 18.3 mi (29.5 km) from the heart of downtown. Enjoy the free cooked breakfast and rooftop terrace. 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.