Tranquil evening seascape on Truman's Beach Marsh in Southold, Long Island, New York, USA

Hotels with Swimming Pools in Southold

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Check availability on Southold Hotels with Swimming Pools

Our top choices for Southold hotels with a pool

Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,009 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is S$168
includes taxes & fees
21 Jun - 22 Jun
Quality Inn Old Saybrook - Westbrook
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (315 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is S$145
includes taxes & fees
14 Jun - 15 Jun
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, (478 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is S$119
includes taxes & fees
17 Jun - 18 Jun
Econo Lodge Inn & Suites Old Saybrook Westbrook
Reception

The Penny Lane

The Penny Lane
2.0 star property
Hampton Bays
9.0 out of 10, Wonderful, (79 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is S$390
includes taxes & fees
6 Jul - 7 Jul
The Penny Lane
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (22 reviews)
The price is S$397
includes taxes & fees
15 Jun - 16 Jun
North Fork Resort
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, (520 reviews)
  • cleanliness
    Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
The price is S$336
includes taxes & fees
14 Jun - 15 Jun
The Bentley Hotel Southampton
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (255 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is S$329
includes taxes & fees
14 Jun - 15 Jun
Cliffside Resort Condominiums
Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,002 reviews)
  • cleanliness
    Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
The price is S$535
includes taxes & fees
21 Jun - 22 Jun
Saybrook Point Resort & Marina
Seasonal outdoor pool

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (315 reviews)
  • cleanliness
    Dip into pool bliss just steps from the ocean at this resort with heated seasonal swimming and tennis courts.
The price is S$423
includes taxes & fees
24 Jun - 25 Jun
Windward Shores Ocean Resort
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, (484 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 S$396
includes taxes & fees
29 Jun - 30 Jun
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.
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Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Beautiful property, close to shops, nice indoor , outdoor pool. Rooms large and comfortable . Staff friendly and excellent service from Beginning to end. Highly recommend !"
Janet 2-night trip
Posted 9 hours ago
Saybrook Point Resort & Marina

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 5 places to stay with pools. During your visit, you can explore sights such as Croteaux Vineyards and The Old Field 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: Offers buffet, a seasonal outdoor pool and free self parking. Vine & Sand: Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Atlantic Hotel: Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Features a seasonal outdoor pool, an indoor pool and a private beach. Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool and 2 bars.
How many pool hotels are there 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 McCabe's Beach and Horton Lane Beach. Discover sights such as Croteaux Vineyards, The Old Field Vineyards and Horton Point Park 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.

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