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Our top choices for Countryside bed & breakfast

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (208 reviews)
"Outstanding! Staff, food, bed…everything was superb We’ll be back soon for sure"
United States
Sigfredo
$268 nightly
The price is $303
Aug 4 - Aug 5
Total with taxes and fees
The Publishing House B&B

Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (149 reviews)
"Very clean and within walking distance to Wrigley Field..."
United States
Robert
$124 nightly
The price is $139
Aug 11 - Aug 12
Total with taxes and fees
Dorothy's

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (529 reviews)
"Great place! Easy street parking and within walking distance to shops and restaurants."
United States
Susan
$195 nightly
The price is $229
Jul 28 - Jul 29
Total with taxes and fees
The Sono Chicago

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very Good, (659 reviews)
"Clean room, self serve breakfast, free street parking permit, cute cats!"
United States
Shu-Ting
$187 nightly
The price is $213
Jul 16 - Jul 17
Total with taxes and fees
The Villa Toscana

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (508 reviews)
"The place is well run. The communal areas are clean and have what you need. The neighborhood is nice, everyone i took was gorgeous! And the perfect distance from the city."
United States
Joanna
$191 nightly
The price is $225
Jul 26 - Jul 27
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (407 reviews)
"The best breakfast I’ve ever had!!"
United States
Sixto
$195 nightly
The price is $221
Jul 16 - Jul 17
Total with taxes and fees
Ray's Bucktown B&B

Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (121 reviews)
"A fantastic stay yet again. I have stayed here the last few years while attending a conference. All the staff were great and amazing selection of food for breakfast and for late night snacks. I will be back again next year"
United Kingdom
Robert
$263 nightly
The price is $309
Jul 28 - Jul 29
Total with taxes and fees
Villa D' Citta

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (129 reviews)
"Spotless room and the best host! Breakfast was warm and delicious."
United States
Christine
$271 nightly
The price is $301
Jul 20 - Jul 21
Total with taxes and fees
Harvey House Bed & Breakfast

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (273 reviews)
"Nice place to stay in an historic neighborhood"
United States
Linda
$278 nightly
The price is $326
Aug 11 - Aug 12
Total with taxes and fees
Wicker Park Inn

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
Humboldt Park
$531 nightly
The price is $542
Aug 11 - Aug 12
Total with taxes and fees
Pristine Apartment with Free Street Parking

Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Lakeview
$1,363 nightly
The price is $1,580
Aug 11 - Aug 12
Total with taxes and fees
Five bedroom - 3 bath - Sleeps 12
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 Countryside Hotel Reviews

Find out more about Countryside

Countryside B&B information

Number of reviews
2,983
Accommodation
14 B&B
Lowest Price
$139
Highest Price
$1,580

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 $139 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.

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