Photo by Monica Ferro

Book Countryside Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Countryside bed & breakfast

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (487)
"The Sono was welcoming, clean and very comfortable. It was easy to find and provided parking! We would absolutely stay here again and would recommend it to friends. "
United States
Ellen
$132 nightly
The price is $155
Dec 30 - Dec 31
Total with taxes and fees
The Sono Chicago

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (190)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
$230 nightly
The price is $260
Jan 29 - Jan 30, 2026
Total with taxes and fees
The Publishing House B&B

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very Good, (98)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
$75 nightly
The price is $82
Jan 18 - Jan 19, 2026
Total with taxes and fees
Dorothy's

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (497)
"Nice shared spaces"
United States
Erica
$141 nightly
The price is $166
Jan 4 - Jan 5, 2026
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (628)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
$81 nightly
The price is $88
Dec 30 - Dec 31
Total with taxes and fees
The Villa Toscana

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (257)
"Fantastic location, spotlessly clean room, and a very comfortable bed. I have stayed here several times and will continue to do so."
United States
Jeffrey
$186 nightly
The price is $218
Jan 4 - Jan 5, 2026
Total with taxes and fees
Wicker Park Inn

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (384)
"Ray's is such a fun, quirky place to stay - tons of creativity has gone into making it a unique stay. The breakfast is fabulous, on-site parking is convenient, and there is excellent attention to safety and security. I thoroughly enjoyed my stay and look forward to visiting again!"
United States
Tala
$163 nightly
The price is $184
Jan 14 - Jan 15, 2026
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, (113)
"Great place"
United States
Jeffrey
$206 nightly
The price is $242
Jan 7 - Jan 8, 2026
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, (121)
"Great hospitality. The suites have a lot of space and amenities. Beautiful location in the heart of Oak Park "
United States
Elizabeth
$231 nightly
The price is $256
Jan 1 - Jan 2, 2026
Total with taxes and fees
Harvey House Bed & Breakfast
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Countryside Hotel Reviews

Find out more about Countryside

Countryside B&B information

Number of reviews
2,551
Accommodation
13 B&B
Lowest Price
$82
Highest Price
$260

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 $82 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.

Explore a world of travel with Expedia