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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 32 B&B in Westchester with updated reviews, rates, and availability.

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.4 out of 10, Very Good, (47)
"Great little spot with all you need. Clean, cozy and a great breakfast!"
$100 nightly
The price is $111
Jun 30 - Jul 1
Total includes taxes and fees
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (572)
"Was a great stay!"
$113 nightly
The price is $126
Jun 30 - Jul 1
Total includes taxes and fees
The Villa Toscana
Ray's Bucktown B&B
Front of property

Ray's Bucktown B&B

3.5 star property
9.8 out of 10, Exceptional, (360)
"Breakfast was great, the staff was kind, and it was a pleasant surprise. "
$190 nightly
The price is $215
Jun 30 - Jul 1
Total includes taxes and fees
Ray's Bucktown B&B
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (463)
"Excellent location. Beautiful property, extremely clean."
$157 nightly
The price is $185
Jun 30 - Jul 1
Total includes taxes and fees
The Sono Chicago
House 5863 - Chicago Bed and Breakfast
Exterior

House 5863 - Chicago Bed and Breakfast

3.5 star property
9.0 out of 10, Wonderful, (473)
"Erick was very friendly and responsive. The neighborhood around was wonderful. We walked everywhere we went and were able to park on the street with no problems. We would stay again. Thank you!"
$168 nightly
The price is $197
Jun 29 - Jun 30
Total includes taxes and fees
House 5863 - Chicago Bed and Breakfast
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (110)
"This was an amazing place to stay, highly recommended for something quiet and relaxing."
$262 nightly
The price is $300
Jul 7 - Jul 8
Total includes taxes and fees
Harvey House Bed & Breakfast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (177)
"Incredible service, amazing breakfast and gorgeous rooms."
$204 nightly
The price is $231
Jul 27 - Jul 28
Total includes taxes and fees
The Publishing House B&B
Wicker Park Inn
Property entrance

Wicker Park Inn

3.5 star property
9.0 out of 10, Wonderful, (247)
"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!"
$275 nightly
The price is $323
Jul 7 - Jul 8
Total includes taxes and fees
Wicker Park Inn
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, (137)
"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
Lobby sitting area

Villa D' Citta

3.5 star property
9.4 out of 10, Exceptional, (101)
"great B&B and so much more. Friendly and helpful staff, this is my 3rd time here"
$263 nightly
The price is $309
Jul 8 - Jul 9
Total includes taxes and fees
Villa D' Citta
Wrigleyville Suites Room 1
Fridge, microwave, oven, stovetop

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...
$215 nightly
The price is $246
Jun 29 - Jun 30
Total includes taxes and fees
Wrigleyville Suites Room 1
Dubois Guest House Room 201
Fridge, microwave, oven, stovetop

Dubois Guest House Room 201

7.4 out of 10, Good, (3)
"We really enjoyed our stay. Cleanliness was top tier. "
$209 nightly
The price is $239
Jun 28 - Jun 29
Total includes taxes and fees
Dubois Guest House Room 201
Villa Dubois Guest House Room 5
Fridge, oven, stovetop, coffee/tea maker

Villa Dubois Guest House Room 5

$205 nightly
The price is $234
Jun 30 - Jul 1
Total includes taxes and fees
Villa Dubois Guest House Room 5
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

$209 nightly
The price is $239
Jun 28 - Jun 29
Total includes taxes and fees
Dubois Guest House Room 101
Villa Dubois Guest House Room 4
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 4

$209 nightly
The price is $239
Jun 28 - Jun 29
Total includes taxes and fees
Villa Dubois Guest House Room 4
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

$209 nightly
The price is $239
Jun 28 - Jun 29
Total includes taxes and fees
Villa Dubois Guest Room 6
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

$209 nightly
The price is $239
Jun 28 - Jun 29
Total includes taxes and fees
Dubois Guest House Room 202
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

$209 nightly
The price is $239
Jun 29 - Jun 30
Total includes taxes and fees
Villa Dubois Guest House Room 2
Dubois Guest House Room 203
Fridge, microwave, oven, stovetop

Dubois Guest House Room 203

$225 nightly
The price is $257
Jun 28 - Jun 29
Total includes taxes and fees
Dubois Guest House Room 203
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
$206 nightly
The price is $235
Jun 29 - Jun 30
Total includes taxes and fees
Wrigleyville Suites Room 2
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 Bed & Breakfast in Westchester?
Prices for B&Bs in Westchester often vary, but you can find a great deal from $111 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.