Photo by Benny Goh

Find Hotels with a Pool in Southold, NY

Start date: Check-in selected.
To Date
End date: Check-out

Check availability on Southold Hotels with a Pool

Top Southold Hotels with a Pool

Seasonal outdoor pool
Vine & Sand

Vine & Sand

3.0 star property
Southold
  • Near private beach
9.6 out of 10, Exceptional, (13)
$320 nightly
The price is $366
Dec 2 - Dec 3
Total with taxes and fees
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, (527)
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.
$178 nightly
The price is $203
Dec 11 - Dec 12
Total with taxes and fees
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.
$72 nightly
The price is $82
Nov 16 - Nov 17
Total with taxes and fees
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, (372)
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.
$118 nightly
The price is $135
Dec 3 - Dec 4
Total with taxes and fees
The Bentley Hotel Southampton
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, (3)
$195 nightly
The price is $223
Nov 11 - Nov 12
Total with taxes and fees
North Fork Cottages & RV Resort
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, (289)
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.
$78 nightly
The price is $90
Nov 11 - Nov 12
Total with taxes and fees
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, (1004)
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.
$101 nightly
The price is $116
Nov 23 - Nov 24
Total with taxes and fees
Quality Inn Old Saybrook - Westbrook
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, (436)
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.
$131 nightly
The price is $147
Nov 11 - Nov 12
Total with taxes and fees
Hamlet Inn
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, (586)
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.
$218 nightly
The price is $249
Nov 11 - Nov 12
Total with taxes and fees
Sound View Greenport
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
Southampton
  • Outdoor pool
7.2 out of 10, Good, (965)
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.
$138 nightly
The price is $158
Nov 24 - Nov 25
Total with taxes and fees
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.
View all properties

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Hospitality at its finest! Bed here was beyond comfortable❤️"
Kelly 1-night trip
Posted 5 days ago
Saybrook Point Resort & Marina

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 Croteaux 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: Offers 2 outdoor pools, an indoor pool, and a full-service spa. Quality Inn Old Saybrook - Westbrook: Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Saybrook Point Resort & Marina: Offers a private beach, a seasonal outdoor pool, and 2 bars. The Atlantic Hotel: Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access.
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 McCabe's Beach and Horton Lane Beach. Discover sights such as Sparkling Pointe, Croteaux Vineyards, and Corey Creek Winery 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.

Explore a world of travel with Expedia