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

Seasonal outdoor pool

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
The price is AED 1,192
AED 1,362 total
includes taxes & fees
12 May - 13 May
Vine & Sand
A heated pool

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 AED 1,177
AED 1,525 total
includes taxes & fees
11 May - 12 May
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
A heated pool

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 AED 1,177
AED 1,525 total
includes taxes & fees
11 May - 12 May
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Outdoor pool, a heated pool

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 AED 1,281
AED 1,661 total
includes taxes & fees
11 May - 12 May
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
A heated pool

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 AED 1,281
AED 1,661 total
includes taxes & fees
11 May - 12 May
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Seasonal outdoor pool

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (308 reviews)
  • cleanliness
    Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
The price is AED 279
AED 321 total
includes taxes & fees
12 May - 13 May
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, (472 reviews)
  • cleanliness
    Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
The price is AED 296
AED 340 total
includes taxes & fees
17 May - 18 May
Econo Lodge Inn & Suites Old Saybrook Westbrook
Down comforters, free WiFi, bed sheets

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 price is AED 792
AED 905 total
includes taxes & fees
11 May - 12 May
The Penny Lane
Seasonal outdoor pool

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.8 out of 10, Excellent, (13 reviews)
The price is AED 718
AED 820 total
includes taxes & fees
12 May - 13 May
North Fork Cottages & RV 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, (490 reviews)
  • cleanliness
    Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
The price is AED 584
AED 667 total
includes taxes & fees
17 May - 18 May
The Bentley Hotel Southampton
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

Hotels with pools and free breakfast in Southold

Interior
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16)
The price is AED 1,192
AED 1,362 total
includes taxes & fees
12 May - 13 May
Vine & Sand
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.
View all properties

Top Southold Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"It was a good experience in general, definitely recommend and I would go back if I need to"
Gloryliz 2-night trip
Posted 2 days ago
The Atlantic Hotel

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