The Best Hotels with a Pool in Southold, NY from ₩140,509 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 : Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Atlantic Hotel : Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Bentley Hotel Southampton : Features a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex : Offers a private beach, a seasonal outdoor pool, and 2 bars.

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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.

₩155,288 total

includes taxes & fees

Jun 18 - Jun 19

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.

₩197,254 total

includes taxes & fees

Jun 21 - Jun 22

The Penny Lane

Hampton Bays

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

₩461,939 total

includes taxes & fees

Jul 6 - Jul 7

North Fork Resort

Greenport

₩507,027 total

includes taxes & fees

Jun 17 - Jun 18

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.

₩140,509 total

includes taxes & fees

Jun 21 - Jun 22

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.

₩405,583 total

includes taxes & fees

Jun 17 - Jun 18

East Hampton House Resort

East Hampton North

Seasonal outdoor pool creates a refreshing escape at this hotel, with tennis courts and gardens adding to the resort atmosphere.

₩649,704 total

includes taxes & fees

Jun 17 - Jun 18

West Neck Guesthouse

Shelter Island Heights

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

₩379,456 total

includes taxes & fees

Jun 22 - Jun 23

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Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

10/10 Excellent

"We had a lovely stay! Loved the room decor. Very calm and relaxing.. looking forward to Returning!"

Water's Edge Resort & Spa

8/10 Good

"The resort was very nice and well maintained. I would say the staff wasn't that great. I've much better experiences. I enjoyed my massage and spa. The only complaint I have is that at a room near mine room was very loud and woke me up at 11:30. I couldn't get a response from dialing 0 and I tried 5x. When I brought it to the attention of the front desk clerk she really didn't seem to care much."

Hyatt Place Long Island East End

10/10 Excellent

"The property itself was nice, and the breakfast was good with a decent selection of options. However, the cleanliness of the room was disappointing. There was a noticeable layer of dust on the tables, coffee machine, and even the glasses, which gave the impression that the room had not been thoroughly cleaned before my stay. While the hotel has some positive aspects, housekeeping standards need improvement."

The Pridwin Hotel

10/10 Excellent

"We had an absolutely enchanting long weekend at the Pridwin. This beautifully appointed property exudes timeless elegance, with thoughtful touches that made us feel truly pampered from the moment the staff reached out to us long before our stay. The complimentary breakfast, in-room snacks and drinks, outdoor fire pits with rocking chairs, and cozy nights spent by the fireplace with bar service turned our visit into a heartfelt home away from home — far warmer and more inviting than any sterile hotel experience. The outdoor heated pool was simply divine, backed by attentive and friendly service that made every swim a pleasure. Shelter Island offers the perfect backdrop for adventure and relaxation — exploring nearby vineyards to the north, or heading south by ferry to Sag Harbor and the broader Hamptons — all while knowing you can retreat each evening to this quiet, serene haven. A special shoutout to Tony, the bartender, whose genuine warmth and friendliness made us feel so welcome every time we crossed paths. Not to mention, he crafts exquisite cocktails and martinis that truly elevated our evenings."

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 The Old Field Vineyards, 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: Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. The Atlantic Hotel: Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Bentley Hotel Southampton: Features a seasonal outdoor pool, an indoor pool, and a private beach. Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool, and 2 bars.

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 McCabe's Beach and Horton Lane Beach. Discover sights such as Croteaux Vineyards, The Old Field Vineyards, 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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