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

Southold Hotels with Swimming Pool

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Check availability on Southold Hotels with Swimming Pools

Next weekend
26 Jun - 28 Jun
In two weeks
3 Jul - 5 Jul

Our top choices for Southold hotels with a pool

Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (317 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is RM405
RM466 total
includes taxes & fees
28 Jun - 29 Jun
Clinton Motel
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, (1,001 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is RM489
RM562 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Old Saybrook - Westbrook
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, (480 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is RM333
RM383 total
includes taxes & fees
28 Jun - 29 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, (80 reviews)
  • cleanliness
    Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
The price is RM1,102
RM1,260 total
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, (24 reviews)
The price is RM1,988
RM2,271 total
includes taxes & fees
22 Jul - 23 Jul
North Fork Resort
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, (1,000 reviews)
  • cleanliness
    Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.
The price is RM1,402
RM1,716 total
includes taxes & fees
30 Jun - 1 Jul
Saybrook Point Resort & Marina
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, (485 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 RM983
RM1,270 total
includes taxes & fees
29 Jun - 30 Jun
Hamlet Inn
Beach nearby

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (39 reviews)
  • cleanliness
    Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
The price is RM906
RM1,035 total
includes taxes & fees
22 Jun - 23 Jun
West Neck Guesthouse
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, (258 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is RM926
RM1,238 total
includes taxes & fees
23 Jun - 24 Jun
Cliffside Resort Condominiums
Seasonal outdoor pool

Budget Host East End

Budget Host East End
2.0 star property
Riverhead
6.8 out of 10, (825 reviews)
  • cleanliness
    Escape summer heat at this serene riverfront motel with a clean, seasonal pool.
The price is RM517
RM591 total
includes taxes & fees
24 Jun - 25 Jun
Budget Host East End
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"The Soundview is one of my favorite hotels in greenport ( favorite) we had an amazing room I never wanted to leave!!"
robyn 2-night trip
Posted 21 hours ago
Sound View Greenport

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 The Hamptons Beaches, and then kick back and relax poolside at one of the accommodation options in Southold that travellers like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Hotel located near The Hamptons Beaches. Offers 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. Pier Blue Inn Old Saybrook - Essex: Offers a seasonal outdoor pool, an indoor pool and a private beach. The Bentley Hotel Southampton: Features a private beach, a seasonal outdoor pool and 2 bars. Water's Edge Resort & Spa: Offers buffet, an indoor pool and free self parking.
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?
Explore places such as The Hamptons Beaches while you're in the area. Make a point to visit attractions such as Horton Lane Beach and McCabe's Beach.
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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