Book the Best Hotels with POOL in Sleepy Hollow in 2026

Q: What are some accommodations with pools in Sleepy Hollow?

Eaglewood Resort and Spa : Features 2 restaurants, an indoor pool, and a full-service spa. Hyatt Regency Schaumburg Chicago : Hotel, 6-minute walk from Woodfield Mall. Offers complimentary wired internet access, an indoor pool, and free self parking. DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove : Provides a snack bar/deli, an indoor pool, and free self parking. Comfort Inn & Suites Arlington Heights - Schaumburg : Offers a snack bar/deli, an indoor pool, and buffet. Hyatt Place Itasca : Hotel located near Woodfield Mall. Offers a snack bar/deli, an indoor pool, and full.

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Our top choices for Sleepy Hollow hotels with a pool

A swimming pool with a tiled deck, lounge chairs, and a view of the outdoors.

1. Best Western Plus Elgin - Chicago

West Dundee

Dive into serenity at this hotel's indoor oasis, complete with loungers for poolside relaxation.

CA $138 total

includes taxes & fees

Nov 11 - Nov 12

An indoor swimming pool with clear water, surrounded by a tiled deck. There are chairs and tables around the pool, and a window with a view of trees outside.

2. Comfort Suites Elgin Northwest

Elgin

Dive into year-round swimming at this modern hotel with an indoor pool that welcomes families to splash and relax anytime.

CA $166 total

includes taxes & fees

Dec 1 - Dec 2

An indoor swimming pool with tiled floors, lounge chairs, and a clear view of the outside through large windows.

3. Holiday Inn Chicago Northwest-Elgin by IHG

Elgin

Soak your cares away in this sparkling indoor pool oasis with inviting hot tub retreat.

CA $213 total

includes taxes & fees

Dec 6 - Dec 7

An indoor swimming pool with blue chairs, a lifeguard chair, and a no diving sign.

4. Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG

Hoffman Estates

Make a splash at the indoor pool getaway just steps from NOW Arena, where refreshing swims meet 24-hour fitness.

CA $163 total

includes taxes & fees

Dec 9 - Dec 10

A swimming pool with a lifeguard chair, a sign warning of no lifeguard on duty, and a checkered wall pattern.

5. Country Inn & Suites by Radisson, Elgin, IL

Elgin

Dive into refreshing relaxation with an indoor pool that's perfect for all-season swimming, just moments from local attractions.

CA $115 total

includes taxes & fees

Dec 6 - Dec 7

An indoor swimming pool with clear blue water, surrounded by large windows offering views of the outdoors.

6. Hampton Inn by Hilton Huntley Chicago

Huntley

Splash into relaxation at this art deco hotel with indoor pool and 24-hour fitness centre.

CA $193 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a tiled deck, a lounge area with chairs, and exercise equipment in the background.

7. Hilton Garden Inn Hoffman Estates

Hoffman Estates

Take a refreshing plunge into indoor pool luxury after a day of Schaumburg adventures at this welcoming hotel.

CA $164 total

includes taxes & fees

Nov 15 - Nov 16

An indoor swimming pool with clear glass ceiling, built-in seating, and a tiled floor.

8. Hyatt Place Chicago/Hoffman Estates

Hoffman Estates

Splash into relaxation at this serene indoor pool oasis with extended hours and poolside comfort.

CA $176 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with a tiled edge, a seating area with chairs, and a door leading to another room.

9. Hampton Inn & Suites Chicago/Hoffman Estates

Hoffman Estates

Dive into pool bliss at this Chicago hotel, where indoor aquatic relaxation awaits.

CA $141 total

includes taxes & fees

Nov 23 - Nov 24

A hotel lobby with a staircase, seating area, and artwork on the walls.

10. Quality Inn and Suites St Charles - West Chicago

St. Charles

Unwind poolside at this modern hotel with a seasonal outdoor pool and lush green surroundings, perfect for summertime splashing.

CA $107 total

includes taxes & fees

Dec 9 - Dec 10

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Choose what matters most at hotels with a pool in Sleepy Hollow

Breakfast included

Hot tub

Top Sleepy Hollow Hotel Reviews

Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG

Hoffman Estates

10/10 Excellent

Shahid

Hilton Garden Inn Hoffman Estates

Hoffman Estates

10/10 Excellent

Ninad

An indoor swimming pool with clear pool rules and a lifeguard warning sign.

Holiday Inn Express Hotel & Suites Chicago-Algonquin by IHG

Algonquin

10/10 Excellent

A great overall experience. The hotel was clean and well kept. The room was clean, spacious and quiet. Wi-fi was excellent; very fast. Service was great. Nice buffet breakfast that includes hot and cold items. Free parking. Keep in mind that this is about a 90-minute drive from downtown Chicago, once you factor in the traffic and construction along the highways. The only downside with the hotel was the fitness centre, which consisted exclusively of 3 treadmills. Nothing else. There was a pool...

Steven

Hampton Inn & Suites Chicago/Hoffman Estates

Hoffman Estates

10/10 Excellent

Mehwish

An indoor swimming pool with clear water, surrounded by tiled walls and a ceiling with recessed lighting.

Country Inn & Suites by Radisson, Schaumburg, IL

Schaumburg

10/10 Excellent

Man Chun

A swimming pool with lounge chairs and a view of greenery outside.

Aloft by Marriott Chicago Schaumburg

Rolling Meadows

10/10 Excellent

Gene

An indoor swimming pool with clear lane markings, a changing room area, and a seating area with lounge chairs.

Fairfield Inn & Suites by Marriott Chicago Schaumburg

Schaumburg

10/10 Excellent

Blair

An indoor swimming pool with clear glass walls, stone flooring, and outdoor seating areas.

Holiday Inn Chicago Nw Crystal Lk Conv Ctr by IHG

Crystal Lake

10/10 Excellent

Craig

Frequently Asked Questions

What are some accommodations with pools in Sleepy Hollow?

Eaglewood Resort and Spa: Features 2 restaurants, an indoor pool, and a full-service spa. Hyatt Regency Schaumburg Chicago: Hotel, 6-minute walk from Woodfield Mall. Offers complimentary wired internet access, an indoor pool, and free self parking. DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove: Provides a snack bar/deli, an indoor pool, and free self parking. Comfort Inn & Suites Arlington Heights - Schaumburg: Offers a snack bar/deli, an indoor pool, and buffet. Hyatt Place Itasca: Hotel located near Woodfield Mall. Offers a snack bar/deli, an indoor pool, and full.

What is there to see and do in Sleepy Hollow?

Make a point to visit attractions like Elgin Sports Complex and Santa's Village. During your stay, check out sights such as Randall Oaks Golf Club, Hemmens Cultural Center, and Grand Victoria Casino.

When is the best time to book a hotel with a pool in Sleepy Hollow?

You may want to consider an accommodation that offers an outdoor pool if you're planning to visit Sleepy Hollow in the hottest 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 visit during the coldest months of January, February, or December when the average temperature is 28°F.

Find Hotels with a Pool in Sleepy Hollow, IL from CA $95

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sleepy Hollow hotels with a pool

1. Best Western Plus Elgin - Chicago

2. Comfort Suites Elgin Northwest

3. Holiday Inn Chicago Northwest-Elgin by IHG

4. Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG

5. Country Inn & Suites by Radisson, Elgin, IL

6. Hampton Inn by Hilton Huntley Chicago

7. Hilton Garden Inn Hoffman Estates

8. Hyatt Place Chicago/Hoffman Estates

9. Hampton Inn & Suites Chicago/Hoffman Estates

10. Quality Inn and Suites St Charles - West Chicago

Choose what matters most at hotels with a pool in Sleepy Hollow

Top Sleepy Hollow Hotel Reviews

Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG

10/10 Excellent

Frequently Asked Questions

What are some accommodations with pools in Sleepy Hollow?

What is there to see and do in Sleepy Hollow?

When is the best time to book a hotel with a pool in Sleepy Hollow?

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