The Best Hotels with a Pool in Southold, NY from NT$2,814 in 2026

Q: What are some accommodations with pools in Southold?

The Shoals Suites and Slips : Offers buffet, a seasonal outdoor pool, and free self parking. Vine & Sand : Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Pier Blue Inn Old Saybrook - Essex : Features a private beach, a seasonal outdoor pool, and 2 bars. The Bentley Hotel Southampton : Offers a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport : Hotel, 1-minute walk from The Hamptons Beaches. Provides daily, a seasonal outdoor pool, and free self parking.

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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.

NT$2,814 total

includes taxes & fees

Jun 3 - Jun 4

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$4,079 total

includes taxes & fees

Jun 7 - Jun 8

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.

NT$2,904 total

includes taxes & fees

Jun 15 - Jun 16

The Penny Lane

Hampton Bays

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

NT$9,871 total

includes taxes & fees

Jun 24 - Jun 25

North Fork Resort

Greenport

NT$10,484 total

includes taxes & fees

Jun 16 - Jun 17

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

Southampton

Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.

NT$7,917 total

includes taxes & fees

Jun 3 - Jun 4

West Neck Guesthouse

Shelter Island Heights

Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.

NT$7,844 total

includes taxes & fees

Jun 9 - Jun 10

Windward Shores Ocean Resort

Napeague

Dip into pool bliss just steps from the ocean at this resort with heated seasonal swimming and tennis courts.

NT$9,508 total

includes taxes & fees

Jun 10 - Jun 11

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Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

Sound View Greenport

10/10 Excellent

"Great"

The Atlantic Hotel

6/10 Okay

"Overall, I had a pleasant stay at this hotel. The room was comfortable, clean upon arrival, and the staff were friendly and helpful when contacted. The only issue I encountered was that I wasn't aware daily housekeeping was not included during my stay. As a result, I had to call the front desk to have my garbage removed and to request a fresh set of towels. Housekeeping came in the evening, but it would have been helpful if the housekeeping policy had been communicated more clearly at check-in or in the room information. Aside from that, my experience was positive."

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 Croteaux Vineyards and Horton Lane Beach, 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, a seasonal outdoor pool, and free self parking. Vine & Sand: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool, and 2 bars. The Bentley Hotel Southampton: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Provides daily, a seasonal outdoor pool, and free self parking.

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?

Enjoy a stroll along the shore at Horton Lane Beach and McCabe's Beach. Discover sights such as Croteaux Vineyards, Corey Creek Winery, and Horton Point Park 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.

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