Southold Hotels with Pool, New York: Southold Hotel Guide

Q: What are some accommodation options with pools in Southold?

The Shoals Suites and Slips : Provides a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex : Features a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport : Hotel located near The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Water's Edge Resort & Spa : Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Bentley Hotel Southampton : Hotel located near Splish Splash Water Park. Provides a snack bar/deli, a seasonal outdoor pool and complimentary high-speed (wired) Internet access.

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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.

includes taxes & fees

20 Jul - 21 Jul

The Penny Lane

Hampton Bays

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

includes taxes & fees

11 Aug - 12 Aug

Quality Inn Old Saybrook - Westbrook

Old Saybrook

Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.

includes taxes & fees

3 Aug - 4 Aug

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 accommodation.

includes taxes & fees

20 Jul - 21 Jul

Hampton's Vacation Inn

Hampton Bays

Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.

includes taxes & fees

28 Jul - 29 Jul

Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Southampton

Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.

includes taxes & fees

4 Aug - 5 Aug

Ocean View Terrace Inn

Hampton Bays

Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.

includes taxes & fees

15 Jul - 16 Jul

North Fork Resort

Greenport

includes taxes & fees

15 Jul - 16 Jul

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Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

Hampton's Vacation Inn

10/10 Excellent

"Staff went above and beyond!! I left an entire drawer filled with stuff and they were so kind to neatly fold and put aside for me till I was able to come and grab it! Room was super clean and spacious property was so cute with a pool and even a Koi fish pond that was right outside our room! Thank you so much for being so kind to us we will be back❤️"

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 5 places to stay with pools. During your visit, you can explore sights such as The Hamptons Beaches, and then kick back and relax poolside at one of the accommodation options in Southold that travellers like for their pools.

What are some accommodation options with pools in Southold?

The Shoals Suites and Slips: Provides a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex: Features a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport: Hotel located near The Hamptons Beaches. Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Water's Edge Resort & Spa: Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Bentley Hotel Southampton: Hotel located near Splish Splash Water Park. Provides a snack bar/deli, a seasonal outdoor pool and complimentary high-speed (wired) Internet access.

How many pool hotels are there in Southold?

Expedia has 5 hotels in Southold for your poolside break.

What is there to see and do in Southold?

Explore places such as The Hamptons Beaches while you're in the area. Make a point to visit attractions such as McCabe's Beach and Horton Lane Beach.

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.

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