Search Hotels with Pool in Westchester

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Check availability on Westchester Hotels with Pool

Tonight
28 Oct - 29 Oct
Tomorrow
29 Oct - 30 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Top Westchester Hotels with Pool

1 bedroom, premium bedding, down duvets, pillow-top beds
The Wade
The Wade
4.5 star property
8.4 out of 10, Very good, (1396)
"Great place to stay"
United States
Adam
The price is ฿3,625
฿4,255 total
includes taxes & fees
23 Nov - 24 Nov
The Wade
Indoor pool
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 star property
8.4 out of 10, Very good, (2045)
"Great place to stay."
United States
Ron
The price is ฿3,442
฿4,857 total
includes taxes & fees
24 Nov - 25 Nov
Palmer House a Hilton Hotel
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers
Aloft Chicago Mag Mile
Aloft Chicago Mag Mile
3.0 star property
8.6 out of 10, Excellent, (2877)
"Had a great stay!"
United States
Josh
The price is ฿3,527
฿4,140 total
includes taxes & fees
23 Nov - 24 Nov
Aloft Chicago Mag Mile
Indoor pool, open 5:00 AM to 11:00 PM, pool loungers
voco Chicago Downtown - Riverwalk by IHG
voco Chicago Downtown - Riverwalk by IHG
3.5 star property
8.8 out of 10, Excellent, (3281)
"Great location, staff very attentive. Hotel was clean and close to riverwalk and downtown "
United States
Rocio
The price is ฿4,245
฿4,983 total
includes taxes & fees
23 Nov - 24 Nov
voco Chicago Downtown - Riverwalk by IHG
Indoor pool
The Royal Sonesta Chicago River North
The Royal Sonesta Chicago River North
4.5 star property
9.2 out of 10, Wonderful, (2207)
"Great stay. Great location."
United States
William
The price is ฿4,278
฿6,067 total
includes taxes & fees
23 Nov - 24 Nov
The Royal Sonesta Chicago River North
Pool
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
8.8 out of 10, Excellent, (1696)
"Excellent hotel in a wonderful location of Chicago!"
United States
Amy
The price is ฿3,025
฿3,552 total
includes taxes & fees
25 Nov - 26 Nov
Hilton Garden Inn Chicago Downtown South Loop
Outdoor pool, pool cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
4.0 star property
8.8 out of 10, Excellent, (2117)
"Great stay "
United States
Melinda
The price is ฿3,370
฿3,956 total
includes taxes & fees
23 Nov - 24 Nov
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
Hyatt Centric Chicago Magnificent Mile
Hyatt Centric Chicago Magnificent Mile
4.0 star property
9.0 out of 10, Wonderful, (1028)
"Great Hotel!"
United States
Wendy
The price is ฿4,147
฿5,827 total
includes taxes & fees
23 Nov - 24 Nov
Hyatt Centric Chicago Magnificent Mile
Indoor pool, seasonal outdoor pool, free pool cabanas, pool loungers
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 star property
8.6 out of 10, Excellent, (1740)
"Excellent Location and beautiful views from the rooms!"
United States
Christina
The price is ฿4,569
฿6,213 total
includes taxes & fees
23 Nov - 24 Nov
Radisson Blu Aqua Hotel Chicago
Indoor pool
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.6 out of 10, Excellent, (5161)
"We enjoyed our stay, great location for walking around downtown. "
United States
Tami
The price is ฿4,136
฿4,855 total
includes taxes & fees
16 Nov - 17 Nov
Embassy Suites by Hilton Chicago Downtown River North
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 Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Excellent stay!"
Stephen 3-night trip
Posted 9 hours ago
The Whitehall Hotel, BW Premier Collection

Frequently asked questions

What are some accommodation options with pools in Westchester?
Congress Plaza Hotel: Hotel, 4-minute walk from Michigan Avenue. Offers full, an indoor pool and flat-screen televisions. Hilton Chicago/Magnificent Mile Suites: Hotel, 4-minute walk from Michigan Avenue. Provides complimentary high-speed (wired) Internet access, an indoor pool and LCD televisions. Freehand Chicago: Hotel, 3-minute walk from Michigan Avenue. Offers a snack bar/deli, an indoor pool and complimentary wireless Internet access. CitizenM Chicago Downtown: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool and a sauna. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from State Street. Provides 2 restaurants, an indoor pool and a health club.
What is there to see and do in Westchester?
While you're in the area, consider exploring places such as Wrigley Field, Michigan Avenue and Navy Pier. Take a walk along the waterfront at Oak Street Beach and North Avenue Beach. The restaurants and shopping are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Westchester?
You may want to consider a place to stay that has an outdoor pool if you plan to visit Westchester in the hottest months of July, August or June, when the average temp is 22°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is -1°C.