The Best Hotels with a Pool in Southold, NY from ₩195,657 in 2026

Q: What are some accommodations with pools in Southold?

The Shoals Suites and Slips : Offers buffet, a seasonal outdoor pool, and free self parking. Vine & Sand : Features a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex : Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport : Features a seasonal outdoor pool, an indoor pool, and a private beach. The Atlantic Hotel : Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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

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Our top choices for Southold hotels with a pool

Seasonal outdoor pool, pool umbrellas, sun loungers

1. Sound View Greenport

Greenport

Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.

₩1,792,473 total

includes taxes & fees

Aug 21 - Aug 22

Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

2. Cliffside Resort Condominiums

Greenport

Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.

₩681,783 total

includes taxes & fees

Aug 6 - Aug 7

3. The Pridwin Hotel

Shelter Island Heights

Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.

₩1,223,511 total

includes taxes & fees

Aug 31 - Sep 1

Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio

4. The Harbor Front Inn

Greenport

Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.

₩788,261 total

includes taxes & fees

Aug 30 - Aug 31

5. Shelter Island House

Shelter Island Heights

Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.

₩520,301 total

includes taxes & fees

Aug 13 - Aug 14

6. North Fork Resort

Greenport

₩869,159 total

includes taxes & fees

Aug 18 - Aug 19

7. West Neck Guesthouse

Shelter Island Heights

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

₩515,779 total

includes taxes & fees

Aug 3 - Aug 4

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

8. Quality Inn Old Saybrook - Westbrook

Old Saybrook

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

₩195,657 total

includes taxes & fees

Aug 25 - Aug 26

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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

"We stayed for 2 nights with our grandchildren. They had a great time and we loved the place. Will definitely consider another stay."

Water's Edge Resort & Spa

8/10 Good

"My husband and I chose this resort for a quiet and relaxing time away and the resort did not disappoint. The grounds are beautiful and meticulously maintained, including the beach and pool area. The room was spacious and very clean as was the whole resort. We got massages at the spa and it was amazing. The only small issue we had was at the restaurants. The food was delicious but they were short staffed on servers which made for delays on taking orders and receiving our food. We did find some great local restaurants though. We really enjoyed our stay and would definitely go back."

Sound View Greenport

10/10 Excellent

"My family and I recently stayed at the Sound View Hotel and had a wonderful experience all thanks to their front desk staffer named Adrianne. While our trip was off to a rough start regarding the initial room we were assigned, the moment I voiced my complaints to Adrianne she stepped in and went above and beyond to ensure we were more than happy with our room, and our overall stay at the hotel. If you want a wonderful getaway in Greenport, look no further!...Adrianne, thank you again for all that you did to make our trip so special. We are so grateful!"

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: Offers buffet, a seasonal outdoor pool, and free self parking. Vine & Sand: Features a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Sound View Greenport: Features a seasonal outdoor pool, an indoor pool, and a private beach. The Atlantic Hotel: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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?

Explore places like The Hamptons Beaches while you're in the area. Make a point to visit attractions like 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 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.

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