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B&B in Crestwood

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (369)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
$185 nightly
The price is $208
Aug 10 - Aug 11
Total includes taxes and fees
Ray's Bucktown B&B

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
$165 nightly
The price is $187
Sep 4 - Sep 5
Total includes taxes and fees
The Publishing House B&B

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (250)
"This was a great alternative to a typical hotel. The staff was extremely helpful and courteous. The room was very nice and the amenities were great. I would definitely stay again!"
$220 nightly
The price is $259
Sep 2 - Sep 3
Total includes taxes and fees
Wicker Park Inn

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (114)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
$262 nightly
The price is $300
Aug 11 - Aug 12
Total includes taxes and fees
Harvey House Bed & Breakfast

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (466)
"Loved the shared kitchen access! "
$168 nightly
The price is $197
Aug 10 - Aug 11
Total includes taxes and fees
The Sono Chicago

Villa Dubois Guest Room 6

$206 nightly
The price is $238
Aug 10 - Aug 11
Total includes taxes and fees
Villa Dubois Guest Room 6

Dubois Guest House Room 101

$246 nightly
The price is $286
Aug 10 - Aug 11
Total includes taxes and fees
Dubois Guest House Room 101

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
$246 nightly
The price is $286
Aug 10 - Aug 11
Total includes taxes and fees
Dubois Guest House Room 201

Villa Dubois Guest House Room 5

$206 nightly
The price is $238
Aug 10 - Aug 11
Total includes taxes and fees
Villa Dubois Guest House Room 5

Villa Dubois Guest House Room 2

$245 nightly
The price is $285
Aug 16 - Aug 17
Total includes taxes and fees
Villa Dubois Guest House Room 2

Dubois Guest House Room 202

2.0 out of 10, (1)
$171 nightly
The price is $196
Aug 10 - Aug 11
Total includes taxes and fees
Dubois Guest House Room 202

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

$192 nightly
The price is $220
Aug 10 - Aug 11
Total includes taxes and fees
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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Top Crestwood Hotel Reviews

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Crestwood?
Prices for B&Bs in Crestwood often vary, but you can find a great deal from $187 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Crestwood B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Crestwood?
The best time to book a B&B in Crestwood is during the vibrant spring months of May through July, when the region comes alive with outdoor activities and cultural events. This peak season attracts travelers who appreciate the lush landscapes and the variety of experiences that Crestwood has to offer. With temperatures ranging from the mid-50s to the high 80s Fahrenheit, visitors can enjoy comfortable weather while indulging in hiking, biking, and exploring the charming local attractions.

July stands out as the most popular month to visit, making it an ideal time for those looking to soak in the lively atmosphere. Many travelers flock to Crestwood for its beautiful parks and engaging community events, creating a superb backdrop for both relaxation and adventure. Whether you're wandering through the picturesque trails or enjoying a picnic in one of the many green spaces, the allure of summer in Crestwood is undeniable.

If you're seeking a more budget-friendly option, consider planning your visit in November. This time of year offers a quieter experience, allowing you to appreciate the serene beauty of Crestwood without the hustle and bustle of peak tourist traffic. You can enjoy the crisp autumn air and take part in local seasonal festivities, which can provide a unique glimpse into the community's culture.
What is the difference between a Crestwood Bed and Breakfast and a hotel?
Every Crestwood B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Crestwood B&Bs.