Hotels with Swimming Pool, Southold New York

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 seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa : Hotel located near Splish Splash Water Park. Offers a seasonal outdoor pool, an indoor pool, and 2 hot tubs. Residence Inn by Marriott New York Long Island East End : Features a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport : Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access.

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Our top choices for Southold hotels with a pool

Vine & Sand

Southold

P26,395 total

includes taxes & fees

Apr 12 - Apr 13

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

Quality Inn Old Saybrook - Westbrook

Old Saybrook

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

P6,913 total

includes taxes & fees

Apr 15 - Apr 16

Clinton Motel

Clinton

Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.

P5,331 total

includes taxes & fees

Apr 15 - Apr 16

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.

P4,889 total

includes taxes & fees

Apr 16 - Apr 17

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.

P8,572 total

includes taxes & fees

Apr 12 - Apr 13

Southampton Long Island Hotel

Southampton

Luxurious poolside retreat with seasonal outdoor oasis and plush sun loungers, just minutes from Cooper's Beach in the Hamptons.

P10,435 total

includes taxes & fees

May 10 - May 11

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Choose what matters most at hotels with a pool in Southold

Breakfast included

4 stars

Top Southold Hotel Reviews

Residence Inn by Marriott New York Long Island East End

6/10 Okay

"Average or below average hotel. Price is too expensive for the quality of the hotel"

Quality Inn Old Saybrook - Westbrook

6/10 Okay

"The checkin staff and later that evening were a 5. Checkout we were not happy with. My daughter got sick and we asked for 12 checkout for her room only. We didn’t say she was sick. She said 11:30. She didn’t tell anyone as housekeeping came to room at 11:20. We called and again asked for time - she said she can have a “few minutes”. We don’t stay at Quality Inns but travel a lot and have never been told no to a later check if needed it. BTW the parking lot was pretty empty so I don’t think they “needed that one room”. Again the younger girl at checking was great and the gentleman later that night were great. "

Saybrook Point Resort & Marina

10/10 Excellent

"Our group of 6 girlfriends had an amazing stay at Saybrook Point Resort & Marina. From the moment we arrived, we knew the weekend was going to be very special. The staff was always warm & welcoming. Shoutout to Scott at reception for ensuring a perfect stay! Dinner at Fresh Salt was delicious & the atmosphere was lively. Shuttle into town was a great option. Can’t wait to book another visit!"

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 Horton Lane Beach and Croteaux Vineyards, and then relax and unwind poolside at one of the accommodations in Southold that guests 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 seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Hotel located near Splish Splash Water Park. Offers a seasonal outdoor pool, an indoor pool, and 2 hot tubs. Residence Inn by Marriott New York Long Island East End: Features a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: 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?

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