Find Hotels with a Pool in Southold, NY

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Southold Hotels with a Pool

This weekend
Next weekend

Top Southold Hotels with a Pool

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 6 places to stay with pools. While you're visiting, you can explore sights such as Sparkling Pointe and Croteaux 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, an indoor pool, and free self parking. Quality Inn Old Saybrook - Westbrook: Offers 2 outdoor pools, an indoor pool, and a full-service spa. Pier Blue Inn Old Saybrook - Essex: Features 2 outdoor tennis courts, a seasonal outdoor pool, and continental. Greenview Inn Riverhead: Hotel, 2-minute walk from The Hamptons Beaches. Provides spa services, a seasonal outdoor pool, and a snack bar/deli. Saybrook Point Resort & Marina: Features a private beach, a seasonal outdoor pool, and 2 bars.
How many pool hotels should I expect to find in Southold?
Expedia has 6 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 Osprey's Dominion 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.