The Best Hotels with a Pool in Southold, NY from AED 1,455 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 : Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport : Hotel located near The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Atlantic Hotel : Features a seasonal outdoor pool, an indoor pool, and a private beach. The Bentley Hotel Southampton : Hotel located near Splish Splash Water Park. Provides a snack bar/deli, a seasonal outdoor pool, and complimentary wired internet access.

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Our top choices for Southold hotels with a pool

Clinton Motel

Clinton

Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.

AED 376 total

includes taxes & fees

29 Jun - 30 Jun

North Fork Resort

Greenport

AED 1,027 total

includes taxes & fees

28 Jun - 29 Jun

Individually decorated, individually furnished, desk, laptop workspace

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.

AED 340 total

includes taxes & fees

7 Jul - 8 Jul

The Penny Lane

Hampton Bays

Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.

AED 1,102 total

includes taxes & fees

14 Jul - 15 Jul

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.

AED 499 total

includes taxes & fees

19 Jul - 20 Jul

Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Old Saybrook Center

Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.

AED 1,439 total

includes taxes & fees

29 Jun - 30 Jun

Hampton's Vacation Inn

Hampton Bays

Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.

AED 755 total

includes taxes & fees

29 Jun - 30 Jun

Ocean View Terrace Inn

Hampton Bays

Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.

AED 1,188 total

includes taxes & fees

1 Jul - 2 Jul

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Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

Hotel Indigo Long Island - East End by IHG

10/10 Excellent

"."

The Pridwin Hotel

8/10 Good

"We were at the Pridwin because of a family wedding on Shelter Island. What an absolutely beautiful hotel! The location is fabulous, right across from the bay and the hotel is designed to really take advantage of the views. Our compliments and thanks to the outstanding staff, they were so warm and helpful! I would go back again in a heartbeat."

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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: Hotel located near The Hamptons Beaches. Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport: Hotel located near The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Atlantic Hotel: Features a seasonal outdoor pool, an indoor pool, and a private beach. The Bentley Hotel Southampton: Hotel located near Splish Splash Water Park. Provides a snack bar/deli, a seasonal outdoor pool, and complimentary wired 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 Horton Lane Beach and McCabe's 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.

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