Find Hotels with a Pool in Sleepy Hollow, IL from CA $133

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Sleepy Hollow Hotels with a Pool

Tonight
Aug 5 - Aug 6
Tomorrow
Aug 6 - Aug 7
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Sleepy Hollow Hotels with a Pool

Ramada Hotel & Conference Center by Wyndham Hammond
Seasonal outdoor pool, pool umbrellas, sun loungers

Ramada Hotel & Conference Center by Wyndham Hammond

2.5 star property
7.4 out of 10, Good, (1003)
"They have wheelchair accessible rooms and bathrooms and the staff was absolutely wonderful We enjoyed our stay there very much"
The price is CA $135
CA $151 total
includes taxes & fees
Aug 6 - Aug 7
Ramada Hotel & Conference Center by Wyndham Hammond
Comfort Suites near I-80 and I-94
Indoor pool

Comfort Suites near I-80 and I-94

2.5 star property
7.0 out of 10, Good, (665)
"Clean and nice"
The price is CA $133
CA $150 total
includes taxes & fees
Sep 4 - Sep 5
Comfort Suites near I-80 and I-94
The Wade
1 bedroom, premium bedding, down comforters, pillowtop beds

The Wade

4.5 star property
8.2 out of 10, Very good, (1156)
"It was a very relaxing stay and amazing view!"
The price is CA $196
CA $230 total
includes taxes & fees
Sep 4 - Sep 5
The Wade
Hyatt Regency McCormick Place Chicago
Indoor pool

Hyatt Regency McCormick Place Chicago

4.0 star property
9.2 out of 10, Wonderful, (1009)
"Great place to stay especially with the price! "
The price is CA $260
CA $338 total
includes taxes & fees
Aug 20 - Aug 21
Hyatt Regency McCormick Place Chicago
Sheraton Grand Chicago Riverwalk
Fitness facility

Sheraton Grand Chicago Riverwalk

4.0 star property
8.4 out of 10, Very good, (1420)
" Great stay, helpful staff, perfectly located. "
The price is CA $302
CA $395 total
includes taxes & fees
Sep 1 - Sep 2
Sheraton Grand Chicago Riverwalk
Loews Chicago Hotel
Indoor pool

Loews Chicago Hotel

4.5 star property
9.4 out of 10, Exceptional, (1516)
"This is a nice hotel in a great neighborhood. "
The price is CA $274
CA $365 total
includes taxes & fees
Sep 1 - Sep 2
Loews Chicago Hotel
Hilton Grand Vacations Club Chicago Magnificent Mile
Seasonal outdoor pool, sun loungers

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 star property
9.2 out of 10, Wonderful, (275)
"walkable to many desireable places."
The price is CA $291
CA $342 total
includes taxes & fees
Aug 24 - Aug 25
Hilton Grand Vacations Club Chicago Magnificent Mile
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Indoor pool

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

4.0 star property
8.2 out of 10, Very good, (2727)
"Wonderful place to stay definitely will return"
The price is CA $240
CA $317 total
includes taxes & fees
Aug 24 - Aug 25
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile
Outdoor pool, sun loungers

DoubleTree by Hilton Chicago - Magnificent Mile

4.0 star property
8.8 out of 10, Excellent, (1958)
"Very pleasant stay!"
The price is CA $219
CA $257 total
includes taxes & fees
Sep 1 - Sep 2
DoubleTree by Hilton Chicago - Magnificent Mile
Radisson Blu Aqua Hotel Chicago
Indoor pool, seasonal outdoor pool, free cabanas, sun loungers

Radisson Blu Aqua Hotel Chicago

4.5 star property
8.4 out of 10, Very good, (1586)
"Lovely hotel and in the most convenient location"
The price is CA $253
CA $339 total
includes taxes & fees
Aug 17 - Aug 18
Radisson Blu Aqua Hotel Chicago
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.

Top Sleepy Hollow Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Very good overall "
Shawn P 5-night trip
Posted 15 hours ago
InterContinental Chicago Magnificent Mile by IHG

Frequently asked questions

What are some accommodations with pools in Sleepy Hollow?
Congress Plaza Hotel: Hotel steps from Michigan Avenue. Offers 2 restaurants, an indoor pool, and a steam room. InterContinental Chicago Magnificent Mile by IHG: 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 wired internet access, an indoor pool, and LCD televisions. Crowne Plaza Chicago West Loop by IHG: Hotel, 8-minute walk from Lake Michigan. Offers a 24-hour fitness center, an indoor pool, and flat-screen televisions. Embassy Suites by Hilton Chicago Downtown River North: Hotel, 3-minute walk from Merchandise Mart. Features 2 restaurants, an indoor pool, and complimentary wireless internet access.
What is there to see and do in Sleepy Hollow?
Explore places like Michigan Avenue, Navy Pier, and Wrigley Field 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.