Southold Hotel Guide - Hotels with Pool in Southold, New York

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Check availability on Southold Hotels with Pool

Our top choices for Southold hotels with a pool

Seasonal outdoor pool
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (13 reviews)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
Outdoor pool, a heated pool
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Southold
10.0 out of 10, Exceptional, (1 review)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
United States
Jessica P.
The price is €381
includes taxes & fees
27 Jan - 28 Jan
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
A heated pool
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Southold
10.0 out of 10, Exceptional, (1 review)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is €357
includes taxes & fees
27 Jan - 28 Jan
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
A heated pool
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Southold
The price is €357
includes taxes & fees
27 Jan - 28 Jan
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
A heated pool
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
The price is €381
includes taxes & fees
27 Jan - 28 Jan
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Seasonal outdoor pool, pool umbrellas, pool loungers
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (606 reviews)
"Nice place"
United States
Mateusz
The price is €156
includes taxes & fees
14 Jan - 15 Jan
Sound View Greenport
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool loungers
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (562 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is €141
includes taxes & fees
15 Jan - 16 Jan
The Harbor Front Inn
Seasonal outdoor pool
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (300 reviews)
"Is good"
United States
Miguel
The price is €75
includes taxes & fees
15 Jan - 16 Jan
Clinton Motel
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, (447 reviews)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is €96
includes taxes & fees
14 Jan - 15 Jan
Hamlet Inn
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, (1,001 reviews)
"Clean and quiet. "
United States
Jeffrey
The price is €110
includes taxes & fees
27 Jan - 28 Jan
Hyatt Place Long Island East End
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 Southold Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Staff was very friendly room was clean and comfortable "
Richard 1-night trip
Posted 1 day ago
The Atlantic Hotel

Frequently asked questions

What's it like visiting Southold?
If laying by the pool is your idea of the perfect getaway, you may want to consider family-friendly Southold, which offers 6 places to stay with pools. During your visit, you can explore sights such as Croteaux Vineyards and Horton Lane Beach, and then kick back and relax poolside at one of the accommodation options in Southold that guests like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Provides a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Pier Blue Inn Old Saybrook - Essex: Features an indoor pool, an outdoor pool and a snack bar/deli. The Bentley Hotel Southampton: Offers a private beach, a seasonal outdoor pool and complimentary cabanas. Hilton Garden Inn Riverhead: Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking.
How many pool hotels are there in Southold?
Expedia has 6 hotels in Southold for your poolside break.
What is there to see and do in Southold?
Enjoy a stroll along the shore at Horton Lane Beach and McCabe's Beach. Discover sights such as Croteaux Vineyards, Corey Creek Winery and Sparkling Pointe during your stay.
When is the best time to book a hotel with a pool in Southold?
You may want to think about a place to stay that offers an outdoor pool if you plan to visit Southold in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or March, when the average temp is 3°C.
What's the best way to travel around Southold?
Knowing the transportation options in Southold can help you enjoy the area beyond your hotel pool. To see more of the larger area, hop on a train at Southold Station. Southold may not have many public transport options to choose from, so consider renting a car to explore more.