Find Hotels with a Pool in Water Mill, NY

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Check availability on Water Mill Hotels with a Pool

Our top choices for Water Mill hotels with a pool

Seasonal outdoor pool
Head of Pond House

Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (3)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
The price is ₩731,466
₩835,700 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Head of Pond House
Pool
Hotel Indigo East End by IHG

Hotel Indigo East End by IHG

Hotel Indigo East End by IHG
3.5 star property
Riverhead
8.8 out of 10, Excellent, (1000)
"The places lovely good restaurant. Nice dinner excellent complimentary breakfast."
United States
Caroline
The price is ₩162,548
₩185,704 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel Indigo East End by IHG
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (443)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is ₩131,664
₩170,173 total
includes taxes & fees
Dec 16 - Dec 17
Hamlet Inn
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (547)
"Awesome stay!!! Great Location "
United States
Bryan
The price is ₩198,161
₩298,718 total
includes taxes & fees
Dec 16 - Dec 17
The Harbor Front Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (396)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is ₩184,899
₩212,725 total
includes taxes & fees
Dec 21 - Dec 22
The Bentley Hotel Southampton
Indoor pool, outdoor pool
Hyatt Place Long Island East End

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1002)
"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"
United States
Helen
The price is ₩165,504
₩189,088 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Hyatt Place Long Island East End
Front of property
The Preston House & Hotel

The Preston House & Hotel

The Preston House & Hotel
3.5 star property
Riverhead
9.8 out of 10, Exceptional, (372)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is ₩203,348
₩232,324 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Preston House & Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is ₩235,251
₩341,114 total
includes taxes & fees
Dec 16 - Dec 17
Sound View Greenport
Seasonal outdoor pool, open 8:00 AM to 7:30 PM, pool umbrellas
Holiday Inn Express Hotel & Suites Long Island-East End by IHG

Holiday Inn Express Hotel & Suites Long Island-East End by IHG

Holiday Inn Express Hotel & Suites Long Island-East End by IHG
2.5 star property
Riverhead
8.6 out of 10, Excellent, (1004)
"Nice room. Good breakfast. Nice lobby and breakfast area. "
United States
Richard
The price is ₩158,115
₩180,647 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Long Island-East End by IHG
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.
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Top Water Mill Hotel Reviews

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Everything was excellent. "
John 2-night trip
Posted 6 days ago
Hilton Garden Inn Riverhead

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Frequently asked questions

What's it like visiting Water Mill?
If laying by the pool is your idea of a great vacation, you may want to check out luxurious Water Mill, which offers 5 places to stay with pools. While you're here, you can explore attractions like Parrish Art Museum and Duck Walk Vineyards, and then kick back and relax poolside at one of the accommodations in Water Mill that guests like for their pools.
What are some accommodations with pools in Water Mill?
Head of Pond House: Features daily, a seasonal outdoor pool, and free self parking. Gurney's Montauk Resort & Seawater Spa: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport: Provides a private beach, a seasonal outdoor pool, and 2 bars. The Bentley Hotel Southampton: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Sea Crest Resort: Offers complimentary wireless internet access, an outdoor pool, and kitchens.
How many pool hotels can I expect to find in Water Mill?
Expedia has 5 hotels in Water Mill for your poolside break.
What is there to see and do in Water Mill?
The picturesque setting of The Hamptons Beaches and Mecox Bay showcase the area's natural beauty. During your stay, check out sights such as Parrish Art Museum, Duck Walk Vineyards, and Atlantic Golf Course.
When is the best time to book a hotel with a pool in Water Mill?
You may want to think about an accommodation that offers an outdoor pool if you're planning to visit Water Mill in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be what you want if you visit during the coldest months of January, February, or March when the average temperature is 38°F.