The Best Hotels with a Pool in Southold, NY from NT$11,691 in 2026

Q: What are some accommodations with pools in Southold?

The Shoals Suites and Slips : Provides a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex : Features a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport : Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Water's Edge Resort & Spa : Features a private beach, a seasonal outdoor pool, and a full-service spa. The Atlantic Hotel : Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

A calm lake with a forest in the background during sunset.

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

Tomorrow

This weekend

Next weekend

Our top choices for Southold hotels with a pool

Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

Cliffside Resort Condominiums

Greenport

Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.

NT$19,799 total

includes taxes & fees

Aug 12 - Aug 13

Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

Greenport

Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.

The Pridwin Hotel

Shelter Island Heights

Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.

NT$29,135 total

includes taxes & fees

Aug 26 - Aug 27

Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio

The Harbor Front Inn

Greenport

Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.

NT$18,366 total

includes taxes & fees

Aug 26 - Aug 27

North Fork Resort

Greenport

NT$15,114 total

includes taxes & fees

Jul 28 - Jul 29

Hyatt Place Long Island East End

Riverhead

Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.

NT$11,800 total

includes taxes & fees

Aug 11 - Aug 12

Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Quality Inn Old Saybrook - Westbrook

Old Saybrook

Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.

NT$4,399 total

includes taxes & fees

Aug 24 - Aug 25

Desk, laptop workspace, iron/ironing board, rollaway beds (surcharge)

Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.

NT$2,998 total

includes taxes & fees

Aug 2 - Aug 3

View all properties

Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

The Hampton Maid

10/10 Excellent

"Amazing place."

Saybrook Point Resort & Marina

10/10 Excellent

"The hotel and marina is a great waterfront property with a nice restaurant, bars, pool (indoor and out) and a spa. The rooms are all recently refurbished and the outdoor amenities for food and drink while watching the boats come in and out of the marina has a great vibe. The staff could not be more accommodating .. overall a great place to stay while traveling through Connecticut (by boat pr by car!)... we have been coming for years and it never disappoints! Lawrence Neustadter"

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 5 places to stay with pools. While you're visiting, you can explore sights such as The Hamptons Beaches, and then relax and unwind poolside at one of the accommodations in Southold that travelers like for their pools.

What are some accommodations with pools in Southold?

The Shoals Suites and Slips: Provides a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Features a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport: Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Water's Edge Resort & Spa: Features a private beach, a seasonal outdoor pool, and a full-service spa. The Atlantic Hotel: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

How many pool hotels should I expect to find in Southold?

Expedia has 5 hotels in Southold for your poolside break.

What is there to see and do in Southold?

Explore places like The Hamptons Beaches while you're in the area. Make a point to visit attractions like McCabe's Beach and Horton Lane Beach.

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.

Explore a world of travel with Expedia

Book Hotels with a Pool in Southold on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Southold Hotels with a Pool