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Hotels with Swimming Pool in Southold, New York

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Check availability on Southold Hotels with Swimming Pool

Top Southold Hotels with Swimming Pool

Seasonal outdoor pool
Vine & Sand

Vine & Sand

3.0 star property
Southold
  • Near private beach
9.6 out of 10, Exceptional, (13)
Vine & Sand
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
The Harbor Front Inn

The Harbor Front Inn

3.5 star property
Greenport
  • Pool loungers
  • Near the beach
8.8 out of 10, Excellent, (535)
Sunlight dances across the seasonal outdoor pool where comfortable loungers invite leisurely afternoons. After swimming, guests appreciate the 24-hour health club, designer bathroom amenities, and continental breakfast before exploring nearby shops and restaurants.
The price is P6,146
P9,906 total
includes taxes & fees
Dec 21 - Dec 22
The Harbor Front Inn
Exterior
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
Old Saybrook
  • Near the beach
7.2 out of 10, Good, (459)
Cooling waters welcome afternoon swimmers to the serene outdoor pool surrounded by lush gardens and a spacious terrace. Individually furnished rooms with modern updates create a comfortable retreat after days spent exploring the Old Saybrook city center.
The price is P4,215
P4,847 total
includes taxes & fees
Nov 30 - Dec 1
Econo Lodge Inn & Suites Old Saybrook Westbrook
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
  • Pool loungers
  • Near private beach
9.6 out of 10, Exceptional, (382)
Swimming awaits at the immaculately clean seasonal outdoor pool where plush loungers invite leisurely afternoons under shady umbrellas. Recently renovated spaces, private beach access just 2 miles away, and proximity to renowned golf courses complete this Southampton retreat.
The price is P6,741
P7,761 total
includes taxes & fees
Nov 24 - Nov 25
The Bentley Hotel Southampton
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Hamlet Inn

Hamlet Inn

2.0 star property
Southampton
  • Pool loungers
  • Near private beach
8.6 out of 10, Excellent, (438)
Refreshing dips await at the seasonal outdoor pool, complete with sun loungers for afternoon relaxation. Nearby water adventures include kayaking, sailing, and surfing, while the private beach provides a peaceful coastal sanctuary.
The price is P4,571
P5,908 total
includes taxes & fees
Nov 22 - Nov 23
Hamlet Inn
Property map
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
  • Pool
  • Kitchen
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
9.4 out of 10, Exceptional, (6)
The price is P11,491
P13,129 total
includes taxes & fees
Nov 23 - Nov 24
North Fork Cottages & RV Resort
Seasonal outdoor pool, pool umbrellas, sun loungers
Sound View Greenport

Sound View Greenport

4.0 star property
Greenport
  • Poolside bar
  • Pool loungers
  • On private beach
8.6 out of 10, Excellent, (593)
Panoramic oceanfront vistas captivate from the seasonal pool area, complete with loungers, umbrellas, and a lively poolside bar. After swimming, guests savor fresh seafood at The Halyard restaurant while watching magnificent sunsets paint the sky.
The price is P9,446
P13,676 total
includes taxes & fees
Dec 22 - Dec 23
Sound View Greenport
Seasonal outdoor pool
Clinton Motel

Clinton Motel

2.5 star property
Clinton
  • Pool
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
8.6 out of 10, Excellent, (293)
Seasonal swimming beckons from July through September in the outdoor pool, complementing days spent exploring nearby beaches. Garden grounds feature barbecue areas and picnic spots, creating a laid-back summer escape just minutes from local cafes.
The price is P4,596
P5,286 total
includes taxes & fees
Dec 1 - Dec 2
Clinton Motel
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 star property
Old Saybrook
  • Indoor pool
  • Pool loungers
7.8 out of 10, Good, (1008)
Swim year-round in the spotless indoor pool, open daily from 9 AM to 9 PM, after exploring nearby Essex attractions. Comfortable sun loungers invite extended relaxation while fitness enthusiasts appreciate the adjacent exercise center.
The price is P5,961
P6,855 total
includes taxes & fees
Nov 30 - Dec 1
Quality Inn Old Saybrook - Westbrook
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
Southampton
  • Outdoor pool
7.2 out of 10, Good, (970)
Splash into vacation mode at the seasonal outdoor pool, a serene oasis complemented by 2 tennis courts. Beyond the hotel grounds, adventure awaits with nearby hiking trails, kayaking, and sailing opportunities for active travelers.
The Atlantic Hotel
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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Top Southold Hotel Reviews

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Very nice place. Nice and clean. Friendly staff. "
Bettyann 1-night trip
Posted 4 days ago
Hyatt Place Long Island East End

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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 6 places to stay with pools. While you're visiting, you can explore sights such as Sparkling Pointe and The Old Field 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: Provides buffet, an indoor pool, and free self parking. Pier Blue Inn Old Saybrook - Essex: Features a private beach, a seasonal outdoor pool, and 2 bars. Quality Inn Old Saybrook - Westbrook: Offers 2 outdoor pools, an indoor pool, and a full-service spa. Sound View Greenport: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Saybrook Point Resort & Marina: Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking.
How many pool hotels should I expect to find in Southold?
Expedia has 6 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, The Old Field 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.