Hotels with Pool & Resorts in Southold

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Check availability on Southold Hotels with Pool

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Best Southold Hotels with Pool

Top Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Beautiful grounds and quiet private beach"
Jaime 2-night trip
Posted 6 days ago
Water's Edge Resort & Spa

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

What's it like visiting Southold?
If laying by the pool is your idea of the perfect getaway, you may want to consider family-friendly Southold, which offers 6 places to stay with pools. During your visit, you can explore sights such as Sparkling Pointe and Croteaux Vineyards, and then kick back and relax poolside at one of the accommodation options in Southold that guests like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Provides buffet, an indoor pool and free self parking. Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool and 2 bars. Quality Inn Old Saybrook - Westbrook: Features 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. New Designer-Built Home with Private Beach: Offers 2 outdoor swimming pools, an indoor pool and a full-service spa. Sound View Greenport: Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
How many pool hotels are there 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 that offers an outdoor pool if you plan to visit Southold in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or March, when the average temp is 3°C.
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 see more of the larger area, hop on a train at Southold Station. Southold may not have many public transport options to choose from, so consider renting a car to explore more.