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

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
"Our room and the entire home was beautifully and charmingly renovated, breakfast was delicious, the room was filled with thoughtful touches, and the pool and hot tub were lovely."
United States
Michelle
The price is ¥61,421
¥70,173 total
includes taxes & fees
May 25 - May 26
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 ¥59,979
¥78,339 total
includes taxes & fees
May 27 - May 28
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)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is ¥59,979
¥78,339 total
includes taxes & fees
May 27 - May 28
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 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 ¥64,487
¥84,218 total
includes taxes & fees
May 27 - May 28
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 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)
"Pool and hot tub divine."
United States
Jessica P.
The price is ¥78,334
¥102,217 total
includes taxes & fees
Jun 1 - Jun 2
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (311 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
"The pool was great"
United States
Michelle
The price is ¥12,549
¥14,431 total
includes taxes & fees
May 26 - May 27
Clinton Motel

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, (474 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
"Pool was open and, while small, it was clean and refreshing. The woman at the front desk was very kind and helpful - made me feel welcome. The property itself is a bit outdated but it looks like they are working to update it. the room was very clean and comfortable for our family of 3. Only issue was the AC system was VERY loud and woke me up every 20 minutes when it went off. I had to shut it off around 3 am and try to salvage my nights sleep. Not sure if this is all rooms or just bad luck on...
United States
Melissa
The price is ¥12,792
¥14,711 total
includes taxes & fees
May 27 - May 28
Econo Lodge Inn & Suites Old Saybrook Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,000 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
"I liked the pool a lot. I think that the hours should be earlier than 9 am to open for us early morning swimmers."
United States
Jill
The price is ¥19,872
¥22,853 total
includes taxes & fees
Jun 3 - Jun 4
Quality Inn Old Saybrook - Westbrook

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (77 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
"The hotel was very clean and the location was very good. It was close to restaurants and beach."
United States
Anonymous traveler
The price is ¥41,308
¥47,195 total
includes taxes & fees
May 28 - May 29
The Penny Lane

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (477 reviews)
  • cleanliness
    Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
"room was clean and comfortable with a nice lil lawn and pool"
United States
Julia
The price is ¥19,157
¥24,760 total
includes taxes & fees
May 26 - May 27
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.

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 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: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool, and 2 bars. The Bentley Hotel Southampton: Hotel, 1-minute walk from The Hamptons Beaches. Offers daily, a seasonal outdoor pool, and free self parking. Sound View Greenport: Provides a seasonal outdoor pool, an indoor pool, and a private beach.
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.