Find Hotels with a Pool in Sleepy Hollow, IL

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 Sleepy Hollow Hotels with a Pool

Tonight
Nov 25 - Nov 26
Tomorrow
Nov 26 - Nov 27
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Top Sleepy Hollow Hotels with a Pool

Indoor pool
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (5297)
"Nice staff A lot of restaurants and stores near the hotel Good breakfast "
United States
Viviana Velazquez
The price is NT$2,891
NT$3,394 total
includes taxes & fees
Dec 8 - Dec 9
Embassy Suites by Hilton Chicago Downtown River North
Indoor pool, seasonal outdoor pool, free cabanas, sun loungers
Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (1785)
"Beautiful location & great service. "
United States
Ariana
The price is NT$4,397
NT$5,978 total
includes taxes & fees
Dec 14 - Dec 15
Radisson Blu Aqua Hotel Chicago
Indoor pool, open 5:00 AM to 11:00 PM, sun loungers
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3398)
"Great hotel!!"
United States
Deja
The price is NT$3,243
NT$3,807 total
includes taxes & fees
Dec 21 - Dec 22
voco Chicago Downtown - Riverwalk by IHG
Indoor pool
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4.0 star property
Downtown Chicago
8.4 out of 10, Very Good, (2096)
"Great place to stay."
United States
Aaron
The price is NT$3,221
NT$4,567 total
includes taxes & fees
Dec 23 - Dec 24
Palmer House a Hilton Hotel
Indoor pool
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2018)
"Great hotel."
United States
Mario
The price is NT$2,994
NT$3,515 total
includes taxes & fees
Dec 15 - Dec 16
Holiday Inn Chicago Dwtn - The Mart by IHG
Indoor pool
Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1042)
"Great Hotel!"
United States
Wendy
The price is NT$3,074
NT$4,532 total
includes taxes & fees
Dec 7 - Dec 8
Hyatt Centric Chicago Magnificent Mile
Outdoor pool, cabanas (surcharge), pool umbrellas
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2153)
"Great stay "
United States
Melinda
The price is NT$3,066
NT$3,599 total
includes taxes & fees
Dec 8 - Dec 9
DoubleTree by Hilton Chicago - Magnificent Mile
Indoor pool
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2273)
"My favorite place to stay when I go to Chicago! "
United States
Sara
The price is NT$3,232
NT$4,801 total
includes taxes & fees
Dec 7 - Dec 8
The Royal Sonesta Chicago River North
1 bedroom, premium bedding, down comforters, pillowtop beds
The Wade

The Wade

4.5 star property
Downtown Chicago
8.4 out of 10, Very Good, (1474)
"Great location, walkable to so many area attractions. Would definitely stay here again. "
United States
Debbie
The price is NT$2,985
NT$3,504 total
includes taxes & fees
Dec 8 - Dec 9
The Wade
Indoor pool, open 7:00 AM to 10:00 PM, sun loungers
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2935)
"Great location!!"
United States
sarah e
The price is NT$2,831
NT$3,323 total
includes taxes & fees
Dec 7 - Dec 8
Aloft Chicago Mag 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

Top Sleepy Hollow Hotel Reviews

Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

10/10 Excellent
"Great stay, close to to cta , bus stop right in downtown "
Susana 2-night trip
Posted 8 hours ago
Club Quarters Hotel, Central Loop, Chicago

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Sleepy Hollow?
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 center. 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 center, an indoor pool, and flat-screen televisions.
What is there to see and do in Sleepy Hollow?
Explore places like Michigan Avenue, Wrigley Field, and United Center while you're in the area. Make a point to visit attractions like Millennium Park and Garfield Park Conservatory.
When is the best time to book a hotel with a pool in Sleepy Hollow?
You may want to consider an accommodation that has an outdoor pool if you're planning to visit in the warmest months of July, August, or June when the average temperature is 70°F. Lodging with an indoor pool may be what you want if you come to town during the coldest months of January, February, or December when the average temperature is 31°F.