Search Hotels with Pool in Southold

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Check availability on Southold Hotels with Pool

Our top choices for Southold hotels with a pool

Seasonal outdoor pool

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
The price is ฿13,854
฿15,828 total
includes taxes & fees
18 May - 19 May
Vine & Sand
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, (473 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.
The price is ฿2,629
฿3,024 total
includes taxes & fees
25 May - 26 May
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (309 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is ฿2,873
฿3,304 total
includes taxes & fees
19 May - 20 May
Clinton Motel
Seasonal outdoor pool

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.2 out of 10, Wonderful, (699 reviews)
  • cleanliness
    Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
The price is ฿5,755
฿6,575 total
includes taxes & fees
20 May - 21 May
The Hampton Maid
Seasonal outdoor pool

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.0 out of 10, Wonderful, (14 reviews)
The price is ฿7,111
฿8,125 total
includes taxes & fees
19 May - 20 May
North Fork Resort
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 ฿3,858
฿4,436 total
includes taxes & fees
8 Jun - 9 Jun
Quality Inn 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.
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Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars

Top Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

6/10 Okay
"Bedding was suboptimal and toilets clogged. Additionally, very noisy due to 2 weddings in the resort that night… so not very relaxing."
Pascale 1-night trip
Posted 4 hours ago
Water's Edge Resort & Spa

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 Sparkling Pointe and Mattebella 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: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Hotel, 1-minute walk from The Hamptons Beaches. Features daily, a seasonal outdoor pool and free self parking. Sag Harbor Inn: Provides a seasonal outdoor pool, an indoor pool and a private beach.
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 Horton Lane Beach and McCabe's Beach. Discover sights such as Sparkling Pointe, Mattebella Vineyards and Croteaux Vineyards 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.