Hotels with Swimming Pool in Southold, New York

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Southold Hotels with Swimming Pool

Next weekend
In two weeks

Our top choices for Southold hotels with a pool

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
Vine & Sand

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (302 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is P4,536
P5,217 total
includes taxes & fees
Feb 23 - Feb 24
Clinton Motel

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (453 reviews)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is P5,025
P6,494 total
includes taxes & fees
Feb 23 - Feb 24
Hamlet Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (568 reviews)
"Lovely hotel with great location in town. Great free breakfast and wonderful staff. We will return! "
United States
Pamela
The price is P7,589
P10,332 total
includes taxes & fees
Feb 23 - Feb 24
The Harbor Front Inn

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (306 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is P7,663
P10,336 total
includes taxes & fees
Feb 25 - Feb 26
Windward Shores Ocean Resort

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, (466 reviews)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is P3,898
P4,483 total
includes taxes & fees
Mar 1 - Mar 2
Econo Lodge Inn & Suites Old Saybrook Westbrook
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.

Choose what matters most at hotels with a pool in Southold

Top Southold Hotel Reviews

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 6 places to stay with pools. While you're visiting, you can explore sights such as The Old Field Vineyards 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: Features a sauna, a pool, and sun loungers. Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars. Water's Edge Resort & Spa: Features a seasonal outdoor pool, an indoor pool, and a private beach. Residence Inn by Marriott New York Long Island East End: Offers a seasonal outdoor pool, an indoor pool, and 2 hot tubs. Hyatt Place Long Island East End: Provides an indoor pool, an outdoor pool, and 2 bars.
How many pool hotels should I expect to find in Southold?
Expedia has 6 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 The Old Field Vineyards, Croteaux Vineyards, 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.

Explore a world of travel with Expedia