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Check prices for these dates

Next weekend
Oct 10 - Oct 12
In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30

B&B in Westchester

Dorothy's
Free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (79)
"Clean room beautiful.yards convenient"
$92 nightly
The price is $102
Oct 6 - Oct 7
Total with taxes and fees
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (610)
"Just a wonderful tranquil oasis in such a large city and busy section of town."
$108 nightly
The price is $120
Oct 5 - Oct 6
Total with taxes and fees
The Villa Toscana
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (477)
"Loved the shared kitchen access! "
$161 nightly
The price is $189
Oct 6 - Oct 7
Total with taxes and fees
The Sono Chicago
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (378)
"Absolutely one of the best stays I’ve ever had. "
$168 nightly
The price is $190
Oct 6 - Oct 7
Total with taxes and fees
Ray's Bucktown B&B
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (185)
"Wonderful staff, beautiful hotel and great breakfast!"
$206 nightly
The price is $233
Oct 26 - Oct 27
Total with taxes and fees
The Publishing House B&B
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (484)
"The space was neat and clean. The bed was really nice comfortable and the breakfast being available whenever was nice to have! Other guests were not an issue and checkin/checkout was very easy."
$161 nightly
The price is $189
Oct 15 - Oct 16
Total with taxes and fees
House 5863 - Chicago Bed and Breakfast
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (252)
"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!"
$229 nightly
The price is $269
Nov 3 - Nov 4
Total with taxes and fees
Wicker Park Inn
Villa D' Citta
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (110)
"Great place"
$240 nightly
The price is $282
Oct 27 - Oct 28
Total with taxes and fees
Villa D' Citta
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (116)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
$231 nightly
The price is $256
Nov 3 - Nov 4
Total with taxes and fees
Harvey House Bed & Breakfast
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (147)
"Great location. Location was clean and everything was good!"
Deluxe Chicago 2 Bedroom Private Condo. Amazing Deal 1.5 mi from Wrigley!
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

Five bedroom - 3 bath - Sleeps 12
Adorable bed & breakfast in Chicago2222
Pool

Adorable bed & breakfast in Chicago2222

2.0 star property
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 Westchester Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Room was clean, staff was friendly and helpful."
Alyssa 1-night trip
Posted 9 hours ago
InterContinental Chicago Magnificent Mile by IHG

Find out more about Westchester

Find out more about Westchester

Westchester B&B information

Number of reviews
2,570
Accommodation
29 B&B
Lowest Price
$102
Highest Price
$282

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 $102 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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