Find Hotels with a Pool in Head of the Harbor, NY

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

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Head of the Harbor Hotels with a Pool

Our top choices for Head of the Harbor hotels with a pool

Indoor pool, open 5:30 AM to 11:00 PM, sun loungers
Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven
2.5 star property
Farmingville
8.8 out of 10, Excellent, (1248)
"The staff is great. The breakfast is good. The rooms are comfortable. "
United States
Kenyata
$103 nightly
The price is $118
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hampton Inn Long Island-Brookhaven
Indoor pool, seasonal outdoor pool, pool umbrellas, sun loungers
Hyatt Regency Long Island

Hyatt Regency Long Island

Hyatt Regency Long Island
4.0 star property
Hauppauge
8.2 out of 10, Very Good, (1083)
"Great place! "
United States
Carla Maeling
$135 nightly
The price is $154
Dec 20 - Dec 21
Total with taxes and fees
Hyatt Regency Long Island
Terrace/patio
Hampton Inn & Suites By Hilton Long Island Farmingdale

Hampton Inn & Suites By Hilton Long Island Farmingdale

Hampton Inn & Suites By Hilton Long Island Farmingdale
2.5 star property
Farmingdale
9.2 out of 10, Wonderful, (89)
"Brand new hotel and room was great. Front desk was very nice and friendly. Breakfast was average but coffee was always available and good. "
United States
Robin
$147 nightly
The price is $168
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hampton Inn & Suites By Hilton Long Island Farmingdale
Indoor pool
The Inn And Spa At East Wind

The Inn And Spa At East Wind

The Inn And Spa At East Wind
3.5 star property
Calverton
8.8 out of 10, Excellent, (878)
"It a beautiful facility, great guest services "
United States
Terry
$109 nightly
The price is $125
Dec 28 - Dec 29
Total with taxes and fees
The Inn And Spa At East Wind
Indoor pool
Hilton Garden Inn Stony Brook

Hilton Garden Inn Stony Brook

Hilton Garden Inn Stony Brook
3.0 star property
Stony Brook
9.0 out of 10, Wonderful, (1002)
"Great visit"
United States
steven
$111 nightly
The price is $127
Dec 21 - Dec 22
Total with taxes and fees
Hilton Garden Inn Stony Brook
Indoor pool
Fairfield Inn by Marriott Medford Long Island

Fairfield Inn by Marriott Medford Long Island

Fairfield Inn by Marriott Medford Long Island
2.5 star property
Medford
8.8 out of 10, Excellent, (1002)
"always an excellent stay "
United States
tanya
$116 nightly
The price is $133
Jan 8 - Jan 9, 2026
Total with taxes and fees
Fairfield Inn by Marriott Medford Long Island
Seasonal outdoor pool
Chalet Inn & Suites Centerport

Chalet Inn & Suites Centerport

Chalet Inn & Suites Centerport
2.0 star property
Centerport
7.8 out of 10, Good, (760)
"A friendly staff and very good location in centerport"
United States
Virna
$120 nightly
The price is $137
Jan 4 - Jan 5, 2026
Total with taxes and fees
Chalet Inn & Suites Centerport
Terrace/patio
Home2 Suites by Hilton Long Island Brookhaven

Home2 Suites by Hilton Long Island Brookhaven

Home2 Suites by Hilton Long Island Brookhaven
3.0 star property
Yaphank
9.2 out of 10, Wonderful, (1002)
"The staff was great and it was very clean "
United States
Michele
$119 nightly
The price is $136
Jan 1 - Jan 2, 2026
Total with taxes and fees
Home2 Suites by Hilton Long Island Brookhaven
Bar (on property)
Residence Inn by Marriott Melville

Residence Inn by Marriott Melville

Residence Inn by Marriott Melville
3.0 star property
Melville
10.0 out of 10, Exceptional, (19)
"Beautiful, spacious and clean. Ideal for a family."
United States
Stephanie
$167 nightly
The price is $191
Dec 21 - Dec 22
Total with taxes and fees
Residence Inn by Marriott Melville
Lobby
Days Inn by Wyndham Woodbury Long Island

Days Inn by Wyndham Woodbury Long Island

Days Inn by Wyndham Woodbury Long Island
2.5 star property
Woodbury
7.2 out of 10, Good, (1001)
"Wonderful and relaxing stay at the Days Inn at Woodbury. Hospitality is great and outside renovations look great. "
United States
Marvie
$94 nightly
The price is $105
Dec 17 - Dec 18
Total with taxes and fees
Days Inn by Wyndham Woodbury Long Island
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 Head of the Harbor Hotel Reviews

Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

10/10 Excellent
"Good"
Ikromjon 1-night trip
Posted 2 days ago
Holiday Inn Express Hauppauge-Long Island

Frequently asked questions

What are some accommodations with pools in Head of the Harbor?
The Bella Vista St James! Waterfront house with a beach dock and so much more!: Offers a seasonal outdoor pool, an indoor pool, and 2 outdoor tennis courts. Hyatt Regency Long Island: Provides free self parking, a pool, and complimentary wireless internet access. Days Inn by Wyndham Woodbury Long Island: Features a snack bar/deli, an indoor pool, and daily. Holiday Inn Express Hauppauge-Long Island: Features a snack bar/deli, an indoor pool, and complimentary wired internet access. La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport: Provides buffet, an indoor pool, and complimentary wired internet access.
What is there to see and do in Head of the Harbor?
Surround yourself with nature at Avalon Park and Preserve. Discover sights such as Stony Brook Grist Mill and Harmony Vineyards during your stay.
When is the best time to book a hotel with a pool in Head of the Harbor?
You may want to consider an accommodation that has an outdoor pool if you plan to visit Head of the Harbor in the hottest months of July, August, or September when the average temp is 72°F. Lodging with an indoor pool may be what you want if you come to town during the coldest months of January, February, or March when the average temperature is 37°F.

Explore a world of travel with Expedia