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Our top choices for Westchester holiday rentals

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.
The price is £336
includes taxes & fees
4 May - 5 May
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

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.
The price is £377
includes taxes & fees
30 Apr - 1 May
King Bed, Game Room & Fire Pit | LCP Collection

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,143 reviews)
"Thank you for the stay"
United States
Marco
The price is £154
includes taxes & fees
10 May - 11 May
Sentral Michigan Avenue

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.8 out of 10, Exceptional, (6 reviews)
The price is £637
includes taxes & fees
1 May - 2 May
ENVITAE Hotel, 4BR Luxury Modern Apartments

River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is £444
includes taxes & fees
5 May - 6 May
River North Rooftop With In and Out Parking 5

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (470 reviews)
"Very clean and nice place"
United States
Hector
The price is £202
includes taxes & fees
30 Apr - 1 May
Level Chicago – Old Town

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.
The price is £175
includes taxes & fees
30 Apr - 1 May
Modern Comfort: 1BR Unit w/ Laundry

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.
The price is £227
includes taxes & fees
4 May - 5 May
Sunlit 1BR Apartment | Warm & Welcoming Space

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.
The price is £453
includes taxes & fees
26 May - 27 May
River North Rooftop With In and Out Parking 3

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"It was very clean and as described/ pictured. The location was absolutely perfect being within a short walk to millennium park, restaurants and stores. The batteries were low in the remote and the host reached out to us around the same time. We received batteries within 10 minutes of letting them know."
United States
Amber W.
The price is £347
includes taxes & fees
5 May - 6 May
LIVN Millennium Park Downtown Chicago 2BR

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

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (191 reviews)
"Having a kitchen is great."
United States
Mark
The price is £271
includes taxes & fees
10 May - 11 May
Kasa River North Chicago

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, (21 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is £598
includes taxes & fees
13 May - 14 May
Modern West Loop Gem-City Views & Prime Location 6

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.
The price is £231
includes taxes & fees
19 May - 20 May
West Loop Living – Bright 1BR

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
The price is £168
includes taxes & fees
10 May - 11 May
Chic Studio in the Heart of the Gold Coast

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.
The price is £373
includes taxes & fees
20 May - 21 May
Spacious 4BR Central Apartment w/ Skyline Views

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Everything went well"
United States
Ryan W.
The price is £140
includes taxes & fees
30 Apr - 1 May
LIVN West Loop Chicago 2 BR City View

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (99 reviews)
"Everything was good!"
United States
Brio
The price is £212
includes taxes & fees
5 May - 6 May
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (74 reviews)
"Nice, clean, safe house."
United States
Adrienne P.
The price is £230
includes taxes & fees
4 May - 5 May
Cozy, Comfortable and Convenient apartment. Close to everything!

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"A cute house with lots of amenities and great location! "
United States
Christie P.
The price is £426
includes taxes & fees
4 May - 5 May
Oak Park Victorian by FLW Studio
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

Find out more about Westchester

Everything you need to know about Westchester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Westchester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Westchester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Westchester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Westchester holiday rentals we have selected for you start as low as £109 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Westchester rentals

At Expedia, we put the best Westchester holiday 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 holiday.

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 holiday rentals in Westchester?

Yes, there are holiday rentals close to the most popular sights in Westchester, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Westchester has to offer?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Westchester is located in the city centre, and offers a BBQ, 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 that you can cook with friends or family.

How many holiday rentals are there in Westchester?

Expedia has 10 holiday 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 favourite places to visit such as Wrigley Field and Navy Pier in the wider area.

What are holiday rentals like in Westchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Westchester. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family trips.