Hotels with Pool & Resorts in Westchester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Westchester Hotels with Pool

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Best Westchester Hotels with Pool

Indoor pool
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
9.2 out of 10, Wonderful, (2266)
Sink into luxurious pool loungers at the inviting indoor sanctuary after exploring nearby Michigan Avenue. Featuring a 24-hour fitness centre, on-site restaurant, and terrace, this hotel perfectly combines aquatic relaxation with urban adventure.
The price is NZ$271
includes taxes & fees
7 Dec - 8 Dec
The Royal Sonesta Chicago River North
Indoor pool
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
8.4 out of 10, Very good, (4186)
Pool enthusiasts revel in year-round swimming at this urban retreat's indoor aquatic haven. Just steps from Michigan Avenue and Millennium Park, guests enjoy Weber Grill dining, convenient shopping, and spacious accommodation.
The price is NZ$166
includes taxes & fees
7 Dec - 8 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Indoor pool, open 7:00 AM to 10:00 PM, pool loungers
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
  • Indoor pool
  • Pool loungers
  • Near the beach
8.6 out of 10, Excellent, (2922)
Dive into relaxation at the inviting indoor pool, perfectly complementing days spent exploring nearby Millennium Park and Navy Pier. Sun loungers provide comfortable respite, while the fitness centre with city views offers 24-hour workout options.
The price is NZ$205
includes taxes & fees
7 Dec - 8 Dec
Aloft Chicago Mag Mile
Indoor pool
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
8.6 out of 10, Excellent, (5283)
Swimming becomes a highlight at the indoor pool sanctuary, where adults supervise children in a pristine environment. After water fun, guests explore Chicago's vibrant riverfront location, just steps from Michigan Avenue shopping and Millennium Park attractions.
The price is NZ$182
includes taxes & fees
21 Dec - 22 Dec
Embassy Suites by Hilton Chicago Downtown River North
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
  • Full-service spa
8.4 out of 10, Very good, (2081)
Sophisticated swimmers relish the year-round indoor pool at this historic treasure near Millennium Park. After invigorating laps, guests can indulge in spa treatments, workout at the 24-hour health club, or explore nearby Chicago landmarks.
The price is NZ$259
includes taxes & fees
21 Dec - 22 Dec
Palmer House a Hilton Hotel
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
Downtown Chicago
  • Indoor pool
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (3382)
Swimmers delight in the spacious indoor pool with glass roof, accessing refreshing waters from early morning until late evening. After laps, guests unwind on comfortable loungers or detoxify in the sauna before dining at the riverside restaurant.
The price is NZ$216
includes taxes & fees
25 Nov - 26 Nov
voco Chicago Downtown - Riverwalk by IHG
1 bedroom, premium bedding, down duvets, pillow-top beds
The Wade

The Wade

4.5 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
8.4 out of 10, Very good, (1463)
Sparkling waters beckon in the sleek indoor pool, a serene oasis amid Chicago's urban energy. Guests appreciate the 5:00 AM to 11:00 PM access, perfect for refreshing dips before exploring Navy Pier or after fitness classes at the 24-hour gym.
The price is NZ$215
includes taxes & fees
26 Nov - 27 Nov
The Wade
Pool
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3.0 star property
Downtown Chicago
  • Pool
  • Pet-friendly
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Gym
8.8 out of 10, Excellent, (1717)
Swimming laps in the refreshing pool creates the perfect interlude between city adventures and relaxation. Minutes from Soldier Field and city centre attractions, this hotel combines Asian cuisine at Shang Noodle with thoughtful amenities for a complete urban retreat.
The price is NZ$166
includes taxes & fees
15 Dec - 16 Dec
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
Downtown Chicago
  • Outdoor pool
  • Poolside bar
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (2142)
Poolside bliss awaits with shaded cabanas, comfortable loungers, and refreshing cocktails from the bar. After swimming, guests can explore Michigan Avenue's attractions, dine at HotHouse restaurant, or energise in the fitness centre.
The price is NZ$204
includes taxes & fees
7 Dec - 8 Dec
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
  • Indoor pool
  • Near the beach
  • Hot tub
9.0 out of 10, Wonderful, (1038)
Bubbling relaxation awaits in the pristine indoor pool and soothing spa pool, perfect complements to an invigorating workout in the state-of-the-art fitness centre. Steps from Chicago's Riverwalk and Millennium Park, this hotel combines aquatic tranquility with urban adventure.
The price is NZ$257
includes taxes & fees
7 Dec - 8 Dec
Hyatt Centric Chicago Magnificent Mile
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.
View all properties

Black Friday Sale

Save up to 40% on select hotels
Book now

Top Westchester Hotel Reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"Our 1 bedroom suite was a fantastic room, very unique touches and "
Brian 1-night trip
Posted 1 day ago
Eurostars Magnificent Mile

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodation options with pools in Westchester?
Embassy Suites by Hilton Chicago Downtown River North: Hotel, 4-minute walk from Michigan Avenue. Features full, an indoor pool and flat-screen televisions. Palmer House a Hilton Hotel: Hotel steps from State Street. Offers a full-service spa, an indoor pool and a 24-hour fitness centre. Hilton Chicago/Magnificent Mile Suites: Hotel steps from Michigan Avenue. Features 2 restaurants, an indoor pool and a sauna. CitizenM Chicago Downtown: Hotel, 4-minute walk from State Street. Offers 2 restaurants, an indoor pool and a health club. Warwick Allerton - Chicago: Hotel, 8-minute walk from Lake Michigan. Features a 24-hour fitness centre, an indoor pool and flat-screen televisions.
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 United Center. 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.