The Best Hotels with a Pool in Southold, NY from ￥23,676 in 2026

Q: What are some accommodations with pools in Southold?

The Shoals Suites and Slips : 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. Water's Edge Resort & Spa : Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport : Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Atlantic Hotel : Hotel, 3-minute walk from The Hamptons Beaches. Offers spa services, a seasonal outdoor pool, and a snack bar/deli.

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

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Our top choices for Southold hotels with a pool

A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.

1. Sound View Greenport

Greenport

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

￥31,988 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.

2. The Harbor Front Inn

Greenport

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

￥28,494 total

includes taxes & fees

Nov 16 - Nov 17

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.

3. Sag Harbor Inn

Sag Harbor

Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.

￥39,475 total

includes taxes & fees

Nov 1 - Nov 2

A poolside area with sun loungers, a pool, and a building with a balcony.

4. Oyster Estate

Greenport

Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.

￥42,143 total

includes taxes & fees

Nov 9 - Nov 10

5. Cliffside Resort Condominiums

Greenport

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

￥47,969 total

includes taxes & fees

Nov 12 - Nov 13

A poolside area with a hat and towel on a lounge chair.

6. North Fork Resort

Greenport

￥55,985 total

includes taxes & fees

Nov 1 - Nov 2

7. Shelter Island House

Shelter Island Heights

Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.

￥46,640 total

includes taxes & fees

Oct 31 - Nov 1

A pool area with umbrellas, potted plants, and a pathway leading to a building.

8. Faraway Sag Harbor

Sag Harbor

Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.

￥63,348 total

includes taxes & fees

Nov 16 - Nov 17

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Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

Hyatt Place Long Island East End

10/10 Excellent

"Great location, great service."

Faraway Sag Harbor

8/10 Good

"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."

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: 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. Water's Edge Resort & Spa: Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Atlantic Hotel: Hotel, 3-minute walk from The Hamptons Beaches. Offers spa services, a seasonal outdoor pool, and a snack bar/deli.

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 Sparkling Pointe, Croteaux Vineyards, and Sannino's Bella Vita Vineyard 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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