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
9.6 out of 10, Exceptional, (15 reviews)
The price is ￥66,026
￥75,435 total
includes taxes & fees
Apr 17 - Apr 18
Vine & Sand
A heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Southold
The price is ￥49,962
￥63,810 total
includes taxes & fees
Mar 18 - Mar 19
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
A heated pool

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Southold
10.0 out of 10, Exceptional, (1 review)
The price is ￥49,962
￥63,810 total
includes taxes & fees
Mar 18 - Mar 19
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Outdoor pool, a heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Southold
10.0 out of 10, Exceptional, (1 review)
The price is ￥54,975
￥70,264 total
includes taxes & fees
Mar 18 - Mar 19
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
A heated pool

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
The price is ￥54,975
￥70,264 total
includes taxes & fees
Mar 18 - Mar 19
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
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, (459 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 ￥15,612
￥20,179 total
includes taxes & fees
Mar 19 - Mar 20
Hamlet Inn
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, (1,003 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is ￥14,744
￥16,955 total
includes taxes & fees
Mar 29 - Mar 30
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (303 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is ￥12,413
￥14,275 total
includes taxes & fees
Mar 24 - Mar 25
Clinton Motel
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, (468 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is ￥10,667
￥12,267 total
includes taxes & fees
Mar 24 - Mar 25
Econo Lodge Inn & Suites Old Saybrook Westbrook
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, (574 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is ￥21,341
￥28,927 total
includes taxes & fees
Mar 22 - Mar 23
The Harbor Front 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

Hotels with pools and free breakfast in Southold

Interior
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15)
The price is ￥66,026
￥75,435 total
includes taxes & fees
Apr 17 - Apr 18
Vine & Sand
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.
View all properties

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

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!"
Eileen 2-night trip
Posted 10 hours ago
Saybrook Point Resort & Marina

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 Croteaux Vineyards and Horton Lane Beach, 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: Provides a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Features a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Offers a seasonal outdoor pool, an indoor pool, and 2 hot tubs. Residence Inn by Marriott New York Long Island East End: Features 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, Osprey's Dominion, 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.