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

Find Hotels with a Pool in Southold, NY

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Check availability on Southold Hotels with a Pool

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Southold hotels with a pool

A modern outdoor seating area with two wicker chairs and a small table, overlooking a body of water and a wooden deck.

1. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (349 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is ₩248,485
₩317,385 total
includes taxes & fees
Nov 1 - Nov 2
The Shoals Suites and Slips
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars

Top Southold Hotel Reviews

Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Perfect experience all around. But very noisy at 8 am - maintenance trucks, etc too loud. Would be better if they started at 9 am. A little jarring to hear the noise right outside rooms so early"
Mary Ann 1-night trip
Posted 20 hours ago
Faraway Sag Harbor

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.