Westchester Vacation Rentals

Vacation Rentals in Westchester

Outdoor pool
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (198)
"This was an amazing place, in a great location, the view was unbelievable, and there was lots of things to do in the area our host, we’re great to work with, they had great insight, and information to share with us to make our stay even more enjoyable. we would definitely use their property again"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
Desk, iron/ironing board, WiFi, bed sheets
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (21)
"We were in town for our son’s wedding and this was the perfect location for our group. Apartment was as advertised and the host was very responsive and helpful. The rooftop provided a perfect place for some pre-wedding groom/best man photos as well."
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
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Lobby
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
10.0 out of 10, Exceptional, (2)
"very close to Michigan Avenue convenience store like a block away. It was a great stay."
The price is $154
$201 total
includes taxes & fees
May 27 - May 28
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
Exterior
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (176)
"Great stay! All of the rooms were wonderful! Really close to food! There are a lot of stairs so make sure you are able to walk up but really great place!"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (30)
"This is one of the best hotels I have ever stayed. Very clean, spacious, and everything is well-designed. Exceed my expectation in every aspect."
The Neighborhood Hotel-Little Italy
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"We stayed here for our daughter's graduation. It was a perfect home base for everything we needed to do. Ross was attentive and thorough in explaining everything we needed to know about the unit, garage parking was a plus, beds were comfortable...overall a great stay."
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"The house was beautifully decorated, well-equipped with all necessary amenities, and perfectly located close to Wrigley Field and the local establishments. If available, I highly recommend upgrading to the garage option for parking, especially during Cubs home games. This worked out perfectly for us. Justin was very helpful and responsive to my questions. We would definitely stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Smart TV, books
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Fridge, microwave, oven, stovetop
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area | Smart TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is $300
$345 total
includes taxes & fees
May 22 - May 23
national historic home near downtown airports no parties no events
Terrace/patio
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (70)
"The house and location was perfect for our group trip to Chicago. Ample rooms and beds for everyone, and host was extremely responsive throughout the process and our stay. Walking distance to a bunch of great restaurants and bars. Would definitely stay again!"
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.4 out of 10, Exceptional, (18)
"The manager had unbelievable communication. He has his phone with him constantly and responds immediately. It's a good walking neighborhood lots of sidewalks and pleasant surroundings. The condo itself is exceptionally clean. For the price in that neighborhood it is a very good value."
The price is $80
$187 total
includes taxes & fees
May 22 - May 23
Chic Suite/Mins to L Train /Laundry/Free Parking
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (405)
"The check in was flawless and got to an impecable room."
The price is $159
$216 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (229)
"Everything was great. From easy check in to easy check out. The room was very nice and cozy. Very clean. Amazing view of downtown from the bedroom and balcony. I will be staying here again! "
Kasa Magnificent Mile Chicago
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is $164
$209 total
includes taxes & fees
May 28 - May 29
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Private kitchen | Fridge, microwave, oven, stovetop
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (298)
"What a nice surprise. First time I have used Sonder. But will not be the last. Great value for the money. "
The price is $182
$214 total
includes taxes & fees
Jun 4 - Jun 5
Sonder South Wabash
Don't see what you're looking for?
See all available properties in Westchester
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.

Westchester Vacation Rental Travel Info

Number of vacation rentals
4
Known landmarks
Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District
International airports
Chicago, IL (ORD-O'Hare Intl.) and Chicago, IL (MDW-Midway Intl.)

Other types of properties in Westchester you may be interested in

View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2883)
"Room was pretty tiny, but manageable. No other complaints. Great location, great staff. "
The price is $169
$198 total
includes taxes & fees
May 27 - May 28
River Hotel
Balcony
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very Good, (1937)
"Nice place for a quick trip to Chicago"
The price is $180
$211 total
includes taxes & fees
May 28 - May 29
Eurostars Magnificent Mile
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2600)
"I don’t really write reviews for places I stay at but this one impressed me beyond my expectations. I planned this trip for my fiancé’s 30th birthday and the location and price of this hotel is the best you will find. Not too far away from everything, conveniently located transportation and so many food choices! My fiancé never shuts up about NYC but Chicago has definitely taken a place in his heart. He even asked to come back. Highly recommend this hotel for everything and beyond."
The price is $125
$162 total
includes taxes & fees
May 27 - May 28
Warwick Allerton - Chicago
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.

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 $82 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.

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?

Your Home Away From Home: This vacation home rental outside of Westchester offers a fireplace, a spa tub, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a microwave to make your meal-planning easier.

How many vacation rentals are there in Westchester?

Expedia has 5 vacation rentals for your stay in Westchester.

What can I see and do in Westchester?

Explore the area and family-friendly sights such as Norridge Park District, or get out into nature at a spot like Grant 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.

Recent reviews of Westchester properties
Expedia verified reviews

River Hotel

River Hotel

5/5 Excellent
Perfect location
"Room was pretty tiny, but manageable. No other complaints. Great location, great staff. "
A verified traveler stayed at River Hotel
Posted 6 hours ago
River Hotel