Top 10 Hotels with Pool & Accommodation in Southold from AU$125

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

The Shoals Suites and Slips : Offers buffet, a seasonal outdoor pool and free self parking. Vine & Sand : Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Pier Blue Inn Old Saybrook - Essex : Features a private beach, a seasonal outdoor pool and 2 bars. The Bentley Hotel Southampton : Offers a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport : Hotel, 1-minute walk from The Hamptons Beaches. Provides daily, a seasonal outdoor pool and free self parking.

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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

3 June - 4 June

Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

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

7 June - 8 June

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

18 June - 19 June

The Penny Lane

Hampton Bays

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

includes taxes & fees

24 June - 25 June

North Fork Resort

Greenport

includes taxes & fees

16 June - 17 June

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

The Bentley Hotel Southampton

Southampton

Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.

includes taxes & fees

22 June - 23 June

West Neck Guesthouse

Shelter Island Heights

Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.

includes taxes & fees

9 June - 10 June

Windward Shores Ocean Resort

Napeague

Dip into pool bliss just steps from the ocean at this resort with heated seasonal swimming and tennis courts.

includes taxes & fees

9 June - 10 June

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Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

Sound View Greenport

10/10 Excellent

"Great"

The Atlantic Hotel

6/10 Okay

"Overall, I had a pleasant stay at this hotel. The room was comfortable, clean upon arrival, and the staff were friendly and helpful when contacted. The only issue I encountered was that I wasn't aware daily housekeeping was not included during my stay. As a result, I had to call the front desk to have my garbage removed and to request a fresh set of towels. Housekeeping came in the evening, but it would have been helpful if the housekeeping policy had been communicated more clearly at check-in or in the room information. Aside from that, my experience was positive."

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 Croteaux Vineyards and Horton Lane Beach, 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: Offers buffet, a seasonal outdoor pool and free self parking. Vine & Sand: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool and 2 bars. The Bentley Hotel Southampton: Offers a seasonal outdoor pool, an indoor pool and a private beach. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Provides daily, a seasonal outdoor pool and free self parking.

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?

Enjoy a stroll along the shore at Horton Lane Beach and McCabe's Beach. Discover sights such as Croteaux Vineyards, Corey Creek Winery and Horton Point Park 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.

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