Find Hotels with a Pool in Southold, NY

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Check availability on Southold Hotels with a Pool

Tonight
Jan 29 - Jan 30
Tomorrow
Jan 30 - Jan 31
This weekend
Jan 30 - Feb 1
Next weekend
Feb 6 - Feb 8

Our top choices for Southold hotels with a pool

Seasonal outdoor 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
Seasonal outdoor pool, pool umbrellas, sun loungers

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (608 reviews)
"Nice place"
United States
Mateusz
The price is ₩191,733
₩259,889 total
includes taxes & fees
Feb 3 - Feb 4
Sound View Greenport
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (563 reviews)
"Everything was Great Immaculate hotel very good location sraff was great"
United States
latoya
The price is ₩191,743
₩259,890 total
includes taxes & fees
Feb 3 - Feb 4
The Harbor Front Inn
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, (448 reviews)
"Room was in good condition however I found the shower to be extremely small despite having great water pressure and extremely nice temperature."
United States
gail
The price is ₩123,505
₩159,627 total
includes taxes & fees
Feb 3 - Feb 4
Hamlet Inn
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (301 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is ₩111,498
₩128,223 total
includes taxes & fees
Feb 1 - Feb 2
Clinton Motel
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (432 reviews)
"Adorable room"
United States
Martin
The price is ₩156,341
₩180,052 total
includes taxes & fees
Feb 8 - Feb 9
The Bentley Hotel Southampton
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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Top Southold Hotel Reviews

Residence Inn by Marriott New York Long Island East End

Residence Inn by Marriott New York Long Island East End

10/10 Excellent
"Absolutely and I'm finally happy and safe with my fiance and I. So thank you 😊 "
Michelle 1-night trip
Posted 2 days ago
Residence Inn by Marriott New York Long Island East End

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 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: Features a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Offers an indoor pool, an outdoor pool, and a snack bar/deli. Sound View Greenport: Features a seasonal outdoor pool, an indoor pool, and a private beach. Hilton Garden Inn Riverhead: Offers a seasonal outdoor pool, an indoor pool, and 2 hot tubs. Water's Edge Resort & Spa: 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 Sparkling Pointe, Croteaux Vineyards, and Sannino's Bella Vita Vineyard 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.