Find Hotels with a Pool in Southold, NY

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Check availability on Southold Hotels with a Pool

Our top choices for Southold hotels with a pool

Seasonal outdoor pool

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
The price is NT$11,376
NT$12,997 total
includes taxes & fees
Apr 19 - Apr 20
Vine & Sand
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (306 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is NT$2,464
NT$2,834 total
includes taxes & fees
Apr 22 - Apr 23
Clinton Motel
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is NT$3,379
NT$3,886 total
includes taxes & fees
Apr 20 - Apr 21
Quality Inn Old Saybrook - Westbrook
Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (471 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is NT$2,399
NT$2,759 total
includes taxes & fees
Apr 26 - Apr 27
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
The price is NT$5,869
NT$6,705 total
includes taxes & fees
Apr 29 - Apr 30
North Fork Cottages & RV Resort
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (469 reviews)
  • cleanliness
    Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
The price is NT$3,521
NT$4,551 total
includes taxes & fees
Apr 23 - Apr 24
Hamlet Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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

Sound View Greenport

8/10 Good
"The check-in staff were friendly and helpful, finding us a different room when ours wasn’t available. The breakfast was significantly better than a simple continental, offering a variety of items. It is a sprawling complex on the LI sound, with nice views from our room and the dining areas. The restaurant, although a bit pricey, had great service, wonderful views, and excellent quality."
Hans 2-night trip
Posted 10 hours ago
Sound View Greenport

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 Sparkling Pointe 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: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Hotel located near Splish Splash Water Park. Features a seasonal outdoor pool, an indoor pool, and 2 hot tubs. Residence Inn by Marriott New York Long Island East End: Offers a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Provides 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 Sparkling Pointe, Croteaux Vineyards, and Corey Creek Winery 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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