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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (171)
"Amazing stay! Great location and beautiful hotel that made you feel cozy"
The price is AED 837
AED 945 total
includes taxes & fees
26 May - 27 May
The Publishing House B&B
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (348)
"What a rad spot...great staff, A M A Z I N G breakfast (can I say Nutella and banana stuffed French toast?!), nice sauna on premise, clean rooms, so much to look at, and I parked in the garage! Will be back...daughters had a blast. "
The price is AED 599
AED 676 total
includes taxes & fees
7 May - 8 May
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (452)
"Was very warm and welcoming.. room was clean and updated… staff was friendly..! Had a great time…"
The price is AED 511
AED 600 total
includes taxes & fees
11 May - 12 May
The Sono Chicago
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (242)
"Great spot for a quick stay!"
The price is AED 1,046
AED 1,228 total
includes taxes & fees
19 May - 20 May
Wicker Park Inn
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"Awesome, comfortable stay good food options would recommend "
The price is AED 960
AED 1,066 total
includes taxes & fees
8 May - 9 May
Harvey House Bed & Breakfast
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 298
AED 623 total
includes taxes & fees
7 May - 8 May
Dubois Guest House Room 201
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

The price is AED 298
AED 623 total
includes taxes & fees
7 May - 8 May
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 298
AED 623 total
includes taxes & fees
7 May - 8 May
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

The price is AED 298
AED 623 total
includes taxes & fees
7 May - 8 May
Dubois Guest House Room 101
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

Dubois Guest House Room 202
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

The price is AED 298
AED 623 total
includes taxes & fees
7 May - 8 May
Villa Dubois Guest House Room 4
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

The price is AED 298
AED 623 total
includes taxes & fees
7 May - 8 May
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

The price is AED 397
AED 742 total
includes taxes & fees
7 May - 8 May
Dubois Guest House Room 203
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)
"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
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

The price is AED 397
AED 742 total
includes taxes & fees
7 May - 8 May
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, (742)
"Great family place to stay. "
The price is AED 528
AED 727 total
includes taxes & fees
11 May - 12 May
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, (492)
"Great stay "
The price is AED 395
AED 464 total
includes taxes & fees
27 May - 28 May
Sonder South Wabash
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (278)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is AED 465
AED 546 total
includes taxes & fees
26 May - 27 May
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: 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. Wicker Park Inn: 11 rooms. 17.4 mi (28.1 km) from the downtown core. The Sono Chicago: 7 rooms. Situated 18 mi (29 km) from the heart of Crestwood. Enjoy the rooftop terrace and fireplace in the lobby. The Publishing House B&B: 11 rooms. 16.1 mi (26 km) from the heart of downtown. Enjoy the free full breakfast and winery. 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.