Southold Hotel Guide - Hotels with Pool in Southold, New York

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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)
Vine & Sand

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 €343
includes taxes & fees
1 Mar - 2 Mar
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--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 €343
includes taxes & fees
1 Mar - 2 Mar
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 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 €377
includes taxes & fees
1 Mar - 2 Mar
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 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 €377
includes taxes & fees
1 Mar - 2 Mar
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (302 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is €76
includes taxes & fees
3 Mar - 4 Mar
Clinton Motel

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (453 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 €117
includes taxes & fees
3 Mar - 4 Mar
Hamlet Inn

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 €98
includes taxes & fees
9 Mar - 10 Mar
Quality Inn Old Saybrook - Westbrook

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (207 reviews)
  • cleanliness
    Luxurious poolside retreat with seasonal outdoor oasis and plush sun loungers, just minutes from Cooper's Beach in the Hamptons.
The price is €120
includes taxes & fees
29 Mar - 30 Mar
Southampton Long Island Hotel

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, (467 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is €65
includes taxes & fees
9 Mar - 10 Mar
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

Hotels with pools and free breakfast in Southold

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.

Top Southold Hotel Reviews

Frequently asked questions

What's it like visiting Southold?
If laying by the pool is your idea of the perfect getaway, you may want to consider family-friendly Southold, which offers 6 places to stay with pools. During your visit, you can explore sights such as The Old Field Vineyards and Croteaux Vineyards, and then kick back and relax poolside at one of the accommodation options in Southold that guests like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Features a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Offers a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Features an indoor pool, an outdoor pool and 2 bars. Hyatt Place Long Island East End: Offers a seasonal outdoor pool, an indoor pool and 2 hot tubs. Residence Inn by Marriott New York Long Island East End: Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
How many pool hotels are there 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 that offers an outdoor pool if you plan to visit Southold in the warmest months of August, July or September, when the average temp is 21°C. Accommodation offering an indoor pool may be the way to go if you visit during the coldest months of January, February or March, when the average temp is 3°C.
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 see more of the larger area, hop on a train at Southold Station. Southold may not have many public transport options to choose from, so consider renting a car to explore more.