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Dec 19 - Dec 21
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Our top choices for Westchester bed & breakfast

Private kitchen
The Sono Chicago

The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (486)
"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
$131 nightly
The price is $154
Dec 18 - Dec 19
Total with taxes and fees
The Sono Chicago
Staircase
The Publishing House B&B

The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (189)
"Wonderful staff, beautiful hotel and great breakfast!"
United States
Veronica
$186 nightly
The price is $211
Dec 18 - Dec 19
Total with taxes and fees
The Publishing House B&B
Living area
Dorothy's

Dorothy's

Dorothy's
3.0 star property
Lakeview
8.4 out of 10, Very Good, (97)
"Can’t beat the price or location. Everything seemed clean and I loved the waffles. "
United States
Ashley
$69 nightly
The price is $75
Dec 18 - Dec 19
Total with taxes and fees
Dorothy's
Courtyard
House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.0 out of 10, Wonderful, (495)
"Cool and clean hotel. Erick was friendly and accommodating."
United States
Samantha
$149 nightly
The price is $174
Jan 4 - Jan 5, 2026
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
Double Room, Private Bathroom (Venetian) | Terrace/patio
The Villa Toscana

The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
7.8 out of 10, Good, (627)
"Good location. Nice room. Shared bath. Excellent value. "
United States
Daniel
$75 nightly
The price is $81
Dec 17 - Dec 18
Total with taxes and fees
The Villa Toscana
Exterior detail
Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking

Pristine Apartment with Free Street Parking
2.0 star property
Humboldt Park
$243 nightly
The price is $248
Dec 16 - Dec 17
Total with taxes and fees
Pristine Apartment with Free Street Parking
Property entrance
Wicker Park Inn

Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (256)
"The Wicker Park Inn is clean, beautifully decorated, and the staff is friendly and helpful!"
United States
Elizabeth R
$186 nightly
The price is $218
Jan 5 - Jan 6, 2026
Total with taxes and fees
Wicker Park Inn
Spa
Ray's Bucktown B&B

Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (382)
"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
$147 nightly
The price is $166
Dec 16 - Dec 17
Total with taxes and fees
Ray's Bucktown B&B
Property entrance
Harvey House Bed & Breakfast

Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (120)
"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
Dec 15 - Dec 16
Total with taxes and fees
Harvey House Bed & Breakfast
Lobby sitting area
Villa D' Citta

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
Dec 16 - Dec 17
Total with taxes and fees
Villa D' Citta
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 Westchester Hotel Reviews

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent
"Cleanliness of the room "
ciera 1-night trip
Posted 2 hours ago
Homewood Suites by Hilton Chicago Downtown South Loop

Find out more about Westchester

Westchester B&B information

Number of reviews
2,538
Accommodation
32 B&B
Lowest Price
$75
Highest Price
$256

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Westchester?
Prices for B&Bs in Westchester often vary, but you can find a great deal from $75 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Westchester 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 B&B in Westchester?
The best time to book a B&B in Westchester is during the vibrant spring months from April to June. This period offers a delightful blend of blooming gardens and mild weather, making it ideal for outdoor activities and sightseeing. Visitors can enjoy exploring the picturesque landscapes of the Hudson River Valley, which is particularly enchanting during this time.

April typically sees temperatures ranging from the low 40s to mid-70s Fahrenheit, providing a comfortable environment for leisurely strolls through the region's historic estates and charming towns. The arrival of spring brings a burst of color, superb for photography enthusiasts and nature lovers alike.

For those looking for a more budget-friendly option, consider visiting in February. While this month is quieter, it offers a unique opportunity to experience Westchester's cozy charm, with fewer crowds at local attractions and the chance to enjoy winter activities such as ice skating in local parks.
What is the difference between a Westchester Bed & Breakfast and a hotel?
Every Westchester 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 Westchester B&Bs.

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