Westchester Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Westchester vacation rentals

Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
$435 nightly
The price is $465
May 11 - May 12
Total with taxes and fees
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Fireplace

King Bed, Game Room & Fire Pit | LCP Collection

King Bed, Game Room & Fire Pit | LCP Collection
Westchester
8.0 out of 10, Very Good, (4 reviews)
"Great location, price and the place was well kept and accommodating."
United States
Carl M.
$526 nightly
The price is $559
May 10 - May 11
Total with taxes and fees
King Bed, Game Room & Fire Pit | LCP Collection
TV, offices

Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway

Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
Westchester
$737 nightly
The price is $780
May 25 - May 26
Total with taxes and fees
Westchester House | Sleeps 10 | Near Chicago & Parks | Close to Restaurants & Easy Local Transport Access | Long private driveway
Living area

Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay

Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay
Westchester
$391 nightly
The price is $418
May 7 - May 8
Total with taxes and fees
Modern Luxury 2BR Near Downtown Chicago - Sleeps 6 & Designer Stay
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,149 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
$177 nightly
The price is $208
May 25 - May 26
Total with taxes and fees
Sentral Michigan Avenue
TV, offices

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.6 out of 10, Exceptional, (27 reviews)
"The apartment is in a good location, close to restaurants and bars. There is a nice park not far away and we had a lovely stay. "
United States
shayna j.
$562 nightly
The price is $693
May 7 - May 8
Total with taxes and fees
3BR Luxury Suite w/Gym and Balcony
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (473 reviews)
"Very clean and nice place"
United States
Hector
$275 nightly
The price is $323
May 11 - May 12
Total with taxes and fees
Level Chicago – Old Town
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (22 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
$561 nightly
The price is $622
May 13 - May 14
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
$525 nightly
The price is $601
May 26 - May 27
Total with taxes and fees
River North Rooftop With In and Out Parking 3
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (192 reviews)
"Having a kitchen is great."
United States
Mark
$319 nightly
The price is $375
May 11 - May 12
Total with taxes and fees
Kasa River North Chicago
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$321 nightly
The price is $366
May 10 - May 11
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
Premium Urban 4BR - Perfect Mix of Comfort & Location
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
$226 nightly
The price is $254
May 7 - May 8
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry
Design Apartment, Private Bathroom (The Oak Park Loft) | Exterior

The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
10.0 out of 10, Exceptional, (5 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
$236 nightly
The price is $268
May 11 - May 12
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
$276 nightly
The price is $313
May 10 - May 11
Total with taxes and fees
West Loop Living – Bright 1BR
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$184 nightly
The price is $217
May 10 - May 11
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (16 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
$391 nightly
The price is $483
May 20 - May 21
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We spent most of this trip discussing our NEXT trip - this stay was one of the simplest, easiest, and most satisfying we've ever experienced with a short-term rental. Hands-down will stay again!Unit incredibly clean, close proximity to the areas we needed to be in, and the host was next-level communicative and kind! Thank you for making it so easy for us!"
United States
Stephanie G.
$209 nightly
The price is $247
May 7 - May 8
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View
TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (35 reviews)
"Only needed some serving and cooking spoons, spatulas, etc., but as I was in a cooking class and not doing much cooking in the apartment it wasn't an issue. Lovely little spot, convenient, very comfortable and the host was available for any questions all hours of the day. Great stay. "
United States
Jan
$189 nightly
The price is $211
May 10 - May 11
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax
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 Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"The bar was well stocked and the bar staff was great!!"
Daynese 1-night trip
Posted 2 hours ago
The Chicago Hotel Collection - Magnificent Mile

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 $161 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This vacation home rental outside of Westchester is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Westchester?

Expedia has 10 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 Navy Pier 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.