Photo by Benny Goh

Find Hotels with a Pool in Southold, NY

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Southold Hotels with a Pool

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Southold Hotels with a Pool

Seasonal outdoor pool
Vine & Sand

Vine & Sand

3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"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

Southold
10.0 out of 10, Exceptional, (1)
"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 SAR 1,336
SAR 1,728 total
includes taxes & fees
1 Jan - 2 January 2026
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

Southold
10.0 out of 10, Exceptional, (1)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is SAR 1,218
SAR 1,575 total
includes taxes & fees
1 Jan - 2 January 2026
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

Southold
The price is SAR 1,218
SAR 1,575 total
includes taxes & fees
1 Jan - 2 January 2026
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

Southold
The price is SAR 1,336
SAR 1,728 total
includes taxes & fees
1 Jan - 2 January 2026
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2.0 star property
Southampton
9.6 out of 10, Exceptional, (390)
"great cost-effective option; room was very spacious and clean."
United States
Isadora
The price is SAR 414
SAR 477 total
includes taxes & fees
22 Dec - 23 Dec
The Bentley Hotel Southampton
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
8.8 out of 10, Excellent, (540)
"Awesome stay!!! Great Location "
United States
Bryan
The price is SAR 492
SAR 746 total
includes taxes & fees
29 Dec - 30 Dec
The Harbor Front Inn
Seasonal outdoor pool
Clinton Motel

Clinton Motel

2.5 star property
Clinton
8.6 out of 10, Excellent, (296)
"Great staff and clean rooms"
United States
Tyler
The price is SAR 293
SAR 337 total
includes taxes & fees
8 Dec - 9 Dec
Clinton Motel
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
8.6 out of 10, Excellent, (439)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is SAR 385
SAR 498 total
includes taxes & fees
18 Dec - 19 Dec
Hamlet Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
Old Saybrook
7.2 out of 10, Good, (460)
"🙂"
United States
Jared
The price is SAR 252
SAR 289 total
includes taxes & fees
5 Jan - 6 January 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
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 Southold Hotel Reviews

Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Staff was courteous and the room was spotless. Food service is very good as well. "
Efrem 1-night trip
Posted 4 days ago
Hilton Garden Inn Riverhead

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Southold?
If lounging next to a pool is your idea of the perfect getaway, you may want to check out family-friendly Southold, which has 6 places to stay with pools. While you're visiting, you can explore sights such as The Old Field Vineyards and Sparkling Pointe, and then relax and unwind poolside at one of the accommodations in Southold that guests like for their pools.
What are some accommodations with pools in Southold?
The Shoals Suites and Slips: Offers buffet, an indoor pool, and free self parking. Quality Inn Old Saybrook - Westbrook: Provides a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Features 2 outdoor pools, an indoor pool, and a full-service spa. Saybrook Point Resort & Marina: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking.
How many pool hotels should I expect to find 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 The Old Field Vineyards, Sparkling Pointe, and Croteaux Vineyards 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 with an outdoor swimming pool if you will be visiting Southold in the warmest months of August, July, or September when the average temp is 70°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or March when the average temp is 38°F.
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 venture out into the surrounding area, ride aboard one of the trains from Southold Station. Southold might not have many public transit options to choose from so consider renting a car to explore more.