Westchester Vacation Rentals

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Dec 9 - Dec 10
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Dec 10 - Dec 11
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Westchester vacation rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1002)
"Beautiful view, and a very nice condo. "
United States
Tiffanie
$143 nightly
The price is $168
Dec 21 - Dec 22
Total with taxes and fees
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (396)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
$223 nightly
The price is $262
Jan 4 - Jan 5, 2026
Total with taxes and fees
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (646)
"Great location and place "
United States
Robert
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (386)
"A very clean and spacious apartment with a great view. The parking garage right next to the building is very convenient. If the water pressure be improved, that will be perfect."
United States
Tammy
Kasa South Loop Chicago
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
$105 nightly
The price is $124
Dec 10 - Dec 11
Total with taxes and fees
Chicago luxury home suites
Property entrance
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (224)
"great place- excellent rooms and near tons of dining "
United States
chris
The Neighborhood Hotel-Little Italy
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
$326 nightly
The price is $383
Dec 12 - Dec 13
Total with taxes and fees
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
$88 nightly
The price is $103
Dec 10 - Dec 11
Total with taxes and fees
Wrigleyville Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-size fridge, microwave, stovetop, dishwasher
The Gem Museum Suites

The Gem Museum Suites

3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (98)
"Great stay. The studio is small but has everything necessary."
United States
Julia
$173 nightly
The price is $199
Dec 17 - Dec 18
Total with taxes and fees
The Gem Museum Suites
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt

Lakeview
9.0 out of 10, Wonderful, (39)
"Great location, apartment was clean, staff was very helpful."
United States
Steve H.
$150 nightly
The price is $165
Dec 10 - Dec 11
Total with taxes and fees
Clean & Equipped 1BR Apt
Terrace/patio
NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO

West Town
10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
$400 nightly
The price is $469
Dec 10 - Dec 11
Total with taxes and fees
Stylish Apartment near Chicago Downtown
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Lakeview 2BR Apartment

Lakeview
9.2 out of 10, Wonderful, (27)
"Great place and area!"
United States
Thomas J.
$165 nightly
The price is $180
Dec 10 - Dec 11
Total with taxes and fees
Lakeview 2BR Apartment
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Downtown Chicago
9.6 out of 10, Exceptional, (14)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
$185 nightly
The price is $203
Dec 11 - Dec 12
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Near West Side
10.0 out of 10, Exceptional, (269)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
TV, offices
Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Great place"
United States
Daniel L.
Modern West Loop Gem-City Views & Prime Location 6
Smart TV, fireplace, printers
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field

Lakeview
10.0 out of 10, Exceptional, (111)
"Got together for a friends reunion in Chicago. The property was perfect and had all the extras in place to make it feel like a home for a few days. I would definitely stay again and highly recommend. "
United States
Jason M.
Wrigleyville Condo, Sleeps 10, 1/2 block from Wrigley Field
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Interior
Urban Farm Fun with Goats 10 Minutes To Downtown!

Urban Farm Fun with Goats 10 Minutes To Downtown!

East Garfield Park
7.8 out of 10, Good, (9)
"Great space, inside and out. Very kind friendly hosts. This was an amazing experience and we are grateful to Nicky and Drew for being so welcoming. "
United States
Jamie A.
Urban Farm Fun with Goats 10 Minutes To Downtown!
Dining
55-56 Mag Mile Penthouse

55-56 Mag Mile Penthouse

Downtown Chicago
10.0 out of 10, Exceptional, (300)
"Great location, great property, great views. "
United States
Mark D.
55-56 Mag Mile Penthouse
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

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"The hotel was beautiful and staff was friendly. It was close and walking distance to a lot of things. Thank you LondonHouse we enjoyed our stay and hope to return in the near future!"
MARISOL 1-night trip
Posted 12 hours ago
LondonHouse Chicago, Curio Collection by Hilton

Find out more about Westchester

Everything you need to know about Westchester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Westchester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Westchester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Westchester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Westchester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Westchester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Westchester rentals

At Expedia, we put the best Westchester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Westchester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Westchester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Westchester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Westchester?

Yes, you can find vacation rentals close to popular points of interest in Westchester, or you can select a secluded option if you want a relaxing place to stay. The shops and restaurants are several reasons why visitors like Westchester. Make sure you have time to check out the basketball games while you're in the area.

What are some of the best vacation rentals that Westchester has to offer?

LakeHouse: This vacation home rental outside of Westchester is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Westchester?

Expedia has 6 vacation rentals for your stay in Westchester.

What can I see and do in Westchester?

Explore the area and family-friendly sights such as Galloping Ghost, or get out into nature at a spot like Millennium Park. You’ll find favorite places to visit like Wrigley Field and Michigan Avenue in the larger area.

What are vacation rentals like in Westchester?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Westchester. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.