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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

B&B in Westchester

Dorothy's
1 bedroom, free WiFi, bed sheets

Dorothy's

3.0 star property
8.2 out of 10, Very Good, (63)
"Great to stay, close walk to many places. Cleaning lady was very helpful and friendly. Rooms a bit small but would definitely stay there again."
$103 nightly
The price is $115
Sep 7 - Sep 8
Total includes taxes and fees
Dorothy's
The Villa Toscana
Exterior

The Villa Toscana

2.5 star property
7.8 out of 10, Good, (590)
"Was a great stay!"
$122 nightly
The price is $136
Sep 8 - Sep 9
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, (369)
"We had an amazing stay at Ray's. They made the entire process from start to finish simple and easy. They went above and beyond for us in many ways and we will definitely be back! "
$168 nightly
The price is $190
Aug 14 - Aug 15
Total includes taxes and fees
Ray's Bucktown 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, (479)
"Everything was taken care of! A wonderful stay. "
$185 nightly
The price is $217
Aug 18 - Aug 19
Total includes taxes and fees
House 5863 - Chicago Bed and Breakfast
The Publishing House B&B
Staircase

The Publishing House B&B

3.5 star property
9.8 out of 10, Exceptional, (181)
"What a lovely place to stay. This bnb was perect!"
$222 nightly
The price is $251
Sep 2 - Sep 3
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, (251)
"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!"
$220 nightly
The price is $259
Sep 2 - Sep 3
Total includes taxes and fees
Wicker Park Inn
Harvey House Bed & Breakfast
Property entrance

Harvey House Bed & Breakfast

4.0 star property
9.8 out of 10, Exceptional, (115)
"Large uniquely, decorated rooms,very comfortable ,great breakfast, great breakfast space, fun conversations at breakfast"
$262 nightly
The price is $300
Aug 14 - Aug 15
Total includes taxes and fees
Harvey House Bed & Breakfast
The Sono Chicago
Private kitchen

The Sono Chicago

3.5 star property
10.0 out of 10, Exceptional, (466)
"Loved the shared kitchen access! "
$178 nightly
The price is $208
Aug 25 - Aug 26
Total includes taxes and fees
The Sono Chicago
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, (143)
"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, (105)
"Would stay again anytime!!"
$286 nightly
The price is $336
Aug 17 - Aug 18
Total includes taxes and fees
Villa D' Citta
Villa Dubois Guest Room 6
Fridge, microwave, oven, stovetop

Villa Dubois Guest Room 6

$138 nightly
The price is $156
Aug 14 - Aug 15
Total includes taxes and fees
Villa Dubois Guest Room 6
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...
$151 nightly
The price is $171
Aug 14 - Aug 15
Total includes taxes and fees
Wrigleyville Suites Room 1
Dubois Guest House Room 101
TV, fireplace, books

Dubois Guest House Room 101

$138 nightly
The price is $156
Aug 14 - Aug 15
Total includes taxes and fees
Dubois Guest House Room 101
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. "
$138 nightly
The price is $156
Aug 14 - Aug 15
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

$210 nightly
The price is $243
Aug 17 - Aug 18
Total includes taxes and fees
Villa Dubois Guest House Room 5
Villa Dubois Guest House Room 2
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 2

$247 nightly
The price is $287
Aug 17 - Aug 18
Total includes taxes and fees
Villa Dubois Guest House Room 2
Dubois Guest House Room 202
Fridge, microwave, oven, stovetop

Dubois Guest House Room 202

2.0 out of 10, (1)
$138 nightly
The price is $156
Aug 14 - Aug 15
Total includes taxes and fees
Dubois Guest House Room 202
Wrigleyville Suites Room 2
Fridge, microwave, oven, stovetop

Wrigleyville Suites Room 2

2.0 star property
2.0 out of 10, (1)
Wrigleyville Suites Room 2
Villa Dubois Guest House Room 1
Fridge, microwave, oven, stovetop

Villa Dubois Guest House Room 1

$289 nightly
The price is $337
Aug 24 - Aug 25
Total includes taxes and fees
Villa Dubois Guest House Room 1
Five bedroom - 3 bath - Sleeps 12
5 bedrooms, free WiFi, bed sheets

Five bedroom - 3 bath - Sleeps 12

$1,108 nightly
The price is $1,279
Aug 19 - Aug 20
Total includes 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 Westchester Hotel Reviews

The Wade

The Wade

10/10 Excellent
"Loved staying at this hotel! This was our second time and we enjoyed it. Super easy to get everywhere and can walk downtown. Would definitely stay here again"
Jacqueline 3-night trip
Posted 11 hours ago
The Wade

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 $115 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.