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B&B in Countryside

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (62)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
$107 nightly
The price is $120
Aug 13 - Aug 14
Total includes taxes and fees
Dorothy's

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (588)
"Was a great stay!"
$117 nightly
The price is $131
Aug 12 - Aug 13
Total includes taxes and fees
The Villa Toscana

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

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (478)
"Everything was taken care of! A wonderful stay. "
$180 nightly
The price is $212
Aug 13 - Aug 14
Total includes taxes and fees
House 5863 - Chicago Bed and Breakfast

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! "
$175 nightly
The price is $206
Aug 10 - Aug 11
Total includes taxes and fees
The Sono Chicago

Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

9.8 out of 10, Exceptional, (143)
"We were thrilled with the little neighborhood and options for food, drinks and shopping. Super easy to hop on bus to and from Wrigley!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (105)
"Would stay again anytime!!"
$229 nightly
The price is $269
Aug 13 - Aug 14
Total includes taxes and fees
Villa D' Citta

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

Wrigleyville Suites Room 1

2.0 star property
2.0 out of 10, (1)
"I would like to say that I was highly disappointed with the customer service, after already having the room booked for over a week I was contacted an hr and a half after check in on the day I was suppose to be there with additional requirements including a $200 fee (Hopefully I get that back) check in was at 3pm I wasnt able to get into my room till 6pm and I had a concert to attend at 8pm this rush caused more stress then it was worth but yes make sure the now $500 room is really worth it...
Wrigleyville Suites Room 1

Wrigleyville Suites Room 3

2.0 star property
$162 nightly
The price is $185
Aug 11 - Aug 12
Total includes taxes and fees
Wrigleyville Suites Room 3

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

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
Wrigleyville Suites 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
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

What is the nightly rate for a B&B in Countryside?
Prices for B&Bs in Countryside often vary, but you can find a great deal from $120 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Countryside 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 Countryside?
The best time to book a B&B in Countryside is during the vibrant spring months of April to June, when the area comes alive with blooming flowers and outdoor activities. This period draws travelers looking to immerse themselves in nature, with opportunities for scenic hikes, leisurely bike rides, and visits to local farmers' markets. The comfortable temperatures, typically ranging from the mid-50s to low 80s Fahrenheit, create an friendly space for exploration and relaxation.

July marks the peak tourist season, with families and adventure seekers flocking to Countryside for its warm weather and numerous outdoor events. The lively ambiance, amplified by community festivals and activities, makes it a fantastic time to engage with the local culture and meet fellow travelers.

For those considering a more budget-conscious trip, October presents a wonderful alternative. The fall season showcases the stunning autumn foliage, particularly along the area's scenic routes. This quieter month allows for tranquil walks among the changing leaves and opportunities to enjoy local harvest festivals, making it a delightful time to experience the charm of Countryside without the crowds.
What is the difference between a Countryside B&B and a hotel?
Every Countryside 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 Countryside B&Bs.