Hotels with Swimming Pool, Southold New York

Q: What are some accommodations 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 wired internet access.

Check availability on Southold Hotels with Swimming Pool

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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.

P6,288 total

includes taxes & fees

Jul 13 - Jul 14

Quality Inn Old Saybrook - Westbrook

Old Saybrook

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

P8,348 total

includes taxes & fees

Aug 2 - Aug 3

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 accommodations.

P5,690 total

includes taxes & fees

Jul 15 - Jul 16

Water's Edge Resort & Spa

Westbrook Center

Pristine waters await at this coastal retreat with private beach access and year-round pools.

P23,212 total

includes taxes & fees

Jul 9 - Jul 10

The Penny Lane

Hampton Bays

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

P19,559 total

includes taxes & fees

Jul 22 - Jul 23

Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Old Saybrook Center

Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.

P29,727 total

includes taxes & fees

Aug 3 - Aug 4

The Hampton Maid

Hampton Bays

Splash into summer at this Hampton motel, where the seasonal pool and massage services await.

P27,481 total

includes taxes & fees

Jul 15 - Jul 16

North Fork Resort

Greenport

P26,091 total

includes taxes & fees

Jul 20 - Jul 21

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Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

Hotel Indigo Long Island - East End by IHG

8/10 Good

"Hotel was convenient and offered a pool to relax, great food in the restaurant! Bed and pillows were very comfortable - we enjoyed our stay to visit the east end."

Saybrook Point Resort & Marina

10/10 Excellent

"Very clean and updated room. Mattress and pillows were very comfortable. Nice furnishings and a large TV. The outdoor pool is not that big so you must get there before 8am to get a lounge. It was great to have a spa on site. My massage therapist was excellent. The check in was painless and the staff was incredibly friendly and helpful with everything. Plenty of parking! I highly recommend this property!!"

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: 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 wired 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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