Search B&B in Crestwood

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 17 B&B in Crestwood with updated reviews, rates, and availability.

Wicker Park Inn
3.5 star property
9.0 out of 10, Wonderful, (237)
"This was the second time that I stayed at this property. The rooms are so beautiful and all the people are so friendly. I love the area and easy access to parking, would definitely stay here again and again! :)"
The price is AED 883
AED 1,036 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Wicker Park Inn
The Sono Chicago
3.5 star property
10.0 out of 10, Exceptional, (432)
"A warm and welcoming beautiful place. The staff was outstanding; from carrying my heavy luggage up three flights to offering great places to eat to accommodating my arrival and departure. Highly recommend. With a spectacular view of the city the rooftop is not to be missed!"
The price is AED 555
AED 652 total
includes taxes & fees
12 Nov 2024 - 13 Nov 2024
The Sono Chicago
Ray's Bucktown B&B
3.5 star property
9.8 out of 10, Exceptional, (328)
"We stayed at Ray’s while visiting Chicago for a concert at The Salt Shed. We’re so happy we took a chance and booked this room! The area is cute, street parking was relatively easy, the room was fun and the whole vibe was very unique and eclectic. There are so many fun accents all over the place. Breakfast was easy and very good! We will be back!"
The price is AED 584
AED 660 total
includes taxes & fees
3 Nov 2024 - 4 Nov 2024
Ray's Bucktown B&B
The Publishing House B&B
3.5 star property
9.8 out of 10, Exceptional, (160)
"Loved it. Wish I would have planned to enjoy more of the amenities "
The price is AED 567
AED 649 total
includes taxes & fees
25 Nov 2024 - 26 Nov 2024
The Publishing House B&B
Harvey House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (103)
"The host is super welcoming and accommodating. I loved spending time in the patio and the size of the room was great. I also found the breakfast and coffee/tea options plentiful."
The price is AED 848
AED 942 total
includes taxes & fees
4 Nov 2024 - 5 Nov 2024
Harvey House Bed & Breakfast
Dubois Guest House Room 201
8.0 out of 10, Very Good, (1)
The price is AED 352
AED 680 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Dubois Guest House Room 201
Villa Dubois Guest House Room 2
The price is AED 392
AED 735 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Villa Dubois Guest House Room 2
Villa Dubois Guest Room 6
The price is AED 322
AED 644 total
includes taxes & fees
25 Nov 2024 - 26 Nov 2024
Villa Dubois Guest Room 6
Villa Dubois Guest House Room 5
The price is AED 307
AED 626 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
The price is AED 307
AED 626 total
includes taxes & fees
12 Nov 2024 - 13 Nov 2024
Dubois Guest House Room 101
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 4
The price is AED 347
AED 674 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Villa Dubois Guest House Room 4
Charming 3 bedrooms Apartment at the Medical District
2.0 star property
10.0 out of 10, Exceptional, (1)
"This place was beautiful and in such a great location!"
Charming 3 bedrooms Apartment at the Medical District
Dubois Guest House Room 202
The price is AED 387
AED 729 total
includes taxes & fees
12 Nov 2024 - 13 Nov 2024
Dubois Guest House Room 202
Villa Dubois Guest House Room 1
The price is AED 441
AED 801 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Villa Dubois Guest House Room 1
Dubois Guest House Room 203
The price is AED 466
AED 835 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Dubois Guest House Room 203
Adorable bed & breakfast in Chicago2222
The price is AED 81
AED 162 total
includes taxes & fees
1 Nov 2024 - 2 Nov 2024
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.
Don't see what you're looking for?
See all available properties in Crestwood
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Crestwood

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (576)
"Very nice place - great location"
The price is AED 459
AED 647 total
includes taxes & fees
11 Nov 2024 - 12 Nov 2024
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.8 out of 10, Excellent, (193)
"Not a lot of self cook food stores nearby "
The price is AED 256
AED 300 total
includes taxes & fees
25 Nov 2024 - 26 Nov 2024
Sonder Market Hall
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (387)
"The apartment was nice. Maybe put a full length mirror in one of the bathrooms….when woman go out they want to look at themselves dressed up for an evening out. "
The price is AED 507
AED 595 total
includes taxes & fees
25 Nov 2024 - 26 Nov 2024
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.

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.