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Our top choices for Westchester vacation rentals
1. Sentral Michigan Avenue
Sentral Michigan Avenue4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,401 reviews)
9.0/10
Wonderful
(1,401 reviews)
"10/10 2nd time staying here!"
"10/10 2nd time staying here!"
Rosa
The price is SAR 507
SAR 507
SAR 596 total
includes taxes & fees
22 Nov - 23 Nov
2. Level Chicago – Old Town
Level Chicago – Old Town4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (557 reviews)
9.2/10
Wonderful
(557 reviews)
"Super clean and friendly staff! Would definitely stay here again"
"Super clean and friendly staff! Would definitely stay here again"Robert Edward
The price is SAR 642
SAR 642
SAR 846 total
includes taxes & fees
23 Nov - 24 Nov
3. Kasa Lake Shore Chicago
Kasa Lake Shore Chicago4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (83 reviews)
8.8/10
Excellent
(83 reviews)
"The bathroom was really clean. The beds were really comfortable"
"The bathroom was really clean. The beds were really comfortable"Jair
The price is SAR 672
SAR 672
SAR 1,022 total
includes taxes & fees
5 Nov - 6 Nov
4. The Gem Museum Suites
The Gem Museum Suites3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (301 reviews)
9.4/10
Exceptional
(301 reviews)
"Good breakfast"
"Good breakfast"Zhaohua
The price is SAR 743
SAR 743
SAR 851 total
includes taxes & fees
5 Dec - 6 Dec
5. Wrigleyville Suites
Wrigleyville Suites2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
9.4/10
Exceptional
(49 reviews)
"Clean room"
"Clean room"Michael
The price is SAR 466
SAR 466
SAR 547 total
includes taxes & fees
5 Nov - 6 Nov
6. Classic Forest Park Foursquare < 1 Mi to Blue Line
Classic Forest Park Foursquare < 1 Mi to Blue Line3.0 star property
Forest Park
The price is SAR 908
SAR 908
SAR 1,782 total
includes taxes & fees
16 Nov - 17 Nov
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.
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.
Find vacation rentals that suit your style
Top Westchester Hotel Reviews
Four Points by Sheraton Chicago Westchester/Oak Brook
Four Points by Sheraton Chicago Westchester/Oak BrookWestchester
10/10 Excellent
It was a wonderful place to stay. Convenient to where we needed to be clean quiet nice place.
It was a wonderful place to stay. Convenient to where we needed to be clean quiet nice place.
Gary
SureStay Plus Hotel by Best Western Chicago Lombard
SureStay Plus Hotel by Best Western Chicago LombardHighland Hills
10/10 Excellent
No complaints
No complaints
Margaret
L7 Chicago by LOTTE
L7 Chicago by LOTTEDowntown Chicago
10/10 Excellent
I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
I stayed here to visit my child that attends the Art Institute and I was completely impressed. I will definitely stay here again.
Erin
LondonHouse Chicago, Curio Collection by Hilton
LondonHouse Chicago, Curio Collection by HiltonDowntown Chicago
10/10 Excellent
Great location
Great location
blerina
Hyatt Regency Chicago
Hyatt Regency ChicagoDowntown Chicago
10/10 Excellent
Wonderful stay in a great location!
Wonderful stay in a great location!
Brooke
Hilton Vacation Club Hotel Blake Chicago
Hilton Vacation Club Hotel Blake ChicagoDowntown Chicago
10/10 Excellent
This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
This was the fourth time I’ve stayed here, and I’ll keep coming back. The location is very handy for families of Columbia College, the rooms are clean, comfortable and well appointed. The staff is extremely friendly and helpful, and it’s priced well.
Jennifer
Holiday Inn Chicago O'Hare – Rosemont by IHG
Holiday Inn Chicago O'Hare – Rosemont by IHGRosemont
10/10 Excellent
I actually like the proximity to the airport. The hotel was clean, had good amenities and has a heated pool.
I actually like the proximity to the airport. The hotel was clean, had good amenities and has a heated pool.
Eero
Residence Inn Chicago Downtown/Loop
Residence Inn Chicago Downtown/LoopDowntown Chicago
10/10 Excellent
Great location!! Walking distance to museums, Navy Pier, Willis Tower, and everything.
Great location!! Walking distance to museums, Navy Pier, Willis Tower, and everything.
Sergio
Hyatt Place Chicago/River North
Hyatt Place Chicago/River NorthDowntown Chicago
10/10 Excellent
Good
Good
Saad
citizenM Chicago Downtown
citizenM Chicago DowntownDowntown Chicago
10/10 Excellent
Great location, clean room and friendly staff!
Great location, clean room and friendly staff!
Diani
Swissotel - Chicago
Swissotel - ChicagoDowntown Chicago
10/10 Excellent
It was okay but, I wish they specified the clearance level for the self parking if we would of have know ahead of time we would of brought our smaller car
It was okay but, I wish they specified the clearance level for the self parking if we would of have know ahead of time we would of brought our smaller car
Brian
Hampton Inn & Suites Chicago Downtown
Hampton Inn & Suites Chicago DowntownDowntown Chicago
10/10 Excellent
I enjoyed my stay here. I didn’t get a chance to experience breakfast or the pool, but it's nice that they're avaliable. I loved the area, very easy to walk for food and entertainment. The bed does need replacing as it makes a squeaking noise when you sit on it and the mattress wasn't that comfortable. Even with that, I would stay here again.
I enjoyed my stay here. I didn’t get a chance to experience breakfast or the pool, but it's nice that they're avaliable. I loved the area, very easy to walk for food and entertainment. The bed does need replacing as it makes a squeaking noise when you sit on it and the mattress wasn't that comfortable. Even with that, I would stay here again.
Shatani
Homewood Suites by Hilton Chicago West Loop Fulton Mkt Area
Homewood Suites by Hilton Chicago West Loop Fulton Mkt AreaDowntown Chicago
10/10 Excellent
Very nice room and facilities. Staff very helpful. Room was fine, but bedcover was snagged - needed replaced. Half and half in kitchen was so old it had congealed - housekeeping should pay closer attention to these details. Nevertheless, I had a good experience overall and would stay there again.
Very nice room and facilities. Staff very helpful. Room was fine, but bedcover was snagged - needed replaced. Half and half in kitchen was so old it had congealed - housekeeping should pay closer attention to these details. Nevertheless, I had a good experience overall and would stay there again.
Lyn
Springhill Suites by Marriott Chicago Downtown/ River North
Springhill Suites by Marriott Chicago Downtown/ River NorthDowntown Chicago
10/10 Excellent
Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.
Recently stayed at the Springhill Suites/River North. Could not have picked a better location for the first time in Chicago. Tons of local dining options. Close to landmarks. Easily walked to the Magnificient Mile(Michigan Ave) Walked to the subway to go to Wrigley Field and the United Center. Hotel was excellent. Clean, the staff was excellent in all areas. Free breakfast was fresh and good. Highly recommend overall.
Michael
Arlo Chicago
Arlo ChicagoDowntown Chicago
10/10 Excellent
Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city!
The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations!
I also highly recommend the lobby bar for a great happy hour spot!!!
Everyone at this hotel...
Arlo Chicago is in the perfect location for walkable access to so many Chicago sights, excellent food (please try the Broken English Taco Pub around the corner!), bars, shopping, etc. It was also very conveniently located to access the L when we needed to get to other parts of the city!
The staff was BEYOND accommodating, friendly, and helpful. The room was clean and exceeded all comfort expectations!
I also highly recommend the lobby bar for a great happy hour spot!!!
Everyone at this hotel...
Lina
Hotel Riu Plaza Chicago
Hotel Riu Plaza ChicagoDowntown Chicago
10/10 Excellent
We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...
We chose this hotel last minute and we were nervous because there were a couple recent negative reviews. There were 4 of us in our family and couldn't find anything negative to say about the hotel. The only disappointing fact was that the rooftop bar was not open but that wasn't a big deal. Everything was very clean. I actually wiped the floor in our room with a wet, white wash cloth, it was clean! There was no hair in the bathroom from a previous guest. There was no hair in the bed from a...
Donna
Hyatt House Chicago/West Loop-Fulton Market
Hyatt House Chicago/West Loop-Fulton MarketDowntown Chicago
10/10 Excellent
The staff was amazing and the room was super spacious and clean!! The best layout of a room for a family of 3 who enjoy separate beds and a little privacy. We had the room with two queen beds and a sofa. Amazing view of chicago from the sky deck and the pool was a nice temp! Breakfast had great options and was delicious! Rosemary seasoned potatoes and captain crunch caught my eye! The elevator was a bit hard to navigate at times as you need a key. But great safety feature so no complaints!...
The staff was amazing and the room was super spacious and clean!! The best layout of a room for a family of 3 who enjoy separate beds and a little privacy. We had the room with two queen beds and a sofa. Amazing view of chicago from the sky deck and the pool was a nice temp! Breakfast had great options and was delicious! Rosemary seasoned potatoes and captain crunch caught my eye! The elevator was a bit hard to navigate at times as you need a key. But great safety feature so no complaints!...
Valia
Hilton Garden Inn Chicago Central Loop
Hilton Garden Inn Chicago Central LoopDowntown Chicago
10/10 Excellent
Was surprised how nice this hotel was! Great location, nice staff, easy check in. Room was very nice! Only thing that I didn't like was 65$ parking I thought would be included with rate but no validation it was added to rate at check in.
Was surprised how nice this hotel was! Great location, nice staff, easy check in. Room was very nice! Only thing that I didn't like was 65$ parking I thought would be included with rate but no validation it was added to rate at check in.
Laura
The Emily Hotel
The Emily HotelDowntown Chicago
10/10 Excellent
Wonderful boutique hotel in excellent Fulton Market area. Walkable to excellent dining and shopping options. The staff were all very friendly and efficient and we loved the convenience of the attached coffee shop.
Wonderful boutique hotel in excellent Fulton Market area. Walkable to excellent dining and shopping options. The staff were all very friendly and efficient and we loved the convenience of the attached coffee shop.
Marvene
Staypineapple, An Iconic Hotel, The Loop
Staypineapple, An Iconic Hotel, The LoopDowntown Chicago
10/10 Excellent
It was great!
It was great!
Natalya
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?
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This vacation home rental outside of Westchester is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease 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 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 Galloping Ghost, or get out into nature at a spot like Millennium Park. You’ll find favorite places to visit like Wrigley Field and Soldier Field 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.