Photo by Benny Goh

Southold Hotel Guide - Hotels with Pool in Southold, New York

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Southold Hotels with Pool

Tonight
27 Nov - 28 Nov
Tomorrow
28 Nov - 29 Nov
This weekend
28 Nov - 30 Nov
Next weekend
5 Dec - 7 Dec

Top Southold Hotels with 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 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, (386)
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 €104
includes taxes & fees
30 Nov - 1 Dec
The Bentley Hotel Southampton
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, (460)
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 centre.
The price is €66
includes taxes & fees
4 Dec - 5 Dec
Econo Lodge Inn & Suites Old Saybrook Westbrook
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool 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, (538)
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 €152
includes taxes & fees
30 Nov - 1 Dec
The Harbor Front Inn
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 €114
includes taxes & fees
30 Nov - 1 Dec
Hamlet Inn
Property map
North Fork Cottages & RV Resort

North Fork Cottages & RV Resort

3.0 star property
Greenport
  • Pool
  • Pet-friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (6)
The price is €192
includes taxes & fees
30 Nov - 1 Dec
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, (294)
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 €77
includes taxes & fees
30 Nov - 1 Dec
Clinton Motel
Indoor pool, open 9:00 AM to 9:00 PM, pool 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, (1011)
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 centre.
The price is €100
includes taxes & fees
3 Dec - 4 Dec
Quality Inn Old Saybrook - Westbrook
Exterior
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 star property
Westbrook Center
  • Indoor pool
  • Pool loungers
  • On private beach
  • Hot tub
8.8 out of 10, Excellent, (1007)
Aquatic splendour awaits at this beachfront resort featuring both indoor and seasonal outdoor pools surrounded by cabanas. Guests can rejuvenate at the spa, enjoy tennis courts, or stroll to the private beach after savouring Italian cuisine at 3 restaurants.
The price is €174
includes taxes & fees
8 Dec - 9 Dec
Water's Edge Resort & Spa
Indoor pool, outdoor pool
Hyatt Place Long Island East End

Hyatt Place Long Island East End

3.0 star property
Riverhead
  • Outdoor pool
  • Indoor pool
  • Poolside bar
9.2 out of 10, Wonderful, (1003)
Sparkling indoor and outdoor swimming pools offer year-round aquatic enjoyment, complemented by a convenient poolside bar for refreshments. After swimming, guests can explore the marina, visit nearby Splish Splash Water Park, or maintain fitness routines.
The price is €121
includes taxes & fees
21 Dec - 22 Dec
Hyatt Place Long Island 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.
View all properties

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Lovely, lovely place. Helpful and nice staff, immaculate rooms. Excellent on site restaurant, Fresh Salt. Great location."
Rose 2-night trip
Posted 2 days ago
Saybrook Point Resort & Marina

Explore a world of travel with Expedia

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 6 places to stay with pools. During your visit, you can explore sights such as The Old Field Vineyards and Sparkling Pointe, 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, an indoor pool and free self parking. Quality Inn Old Saybrook - Westbrook: Provides a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Features 2 outdoor swimming pools, an indoor pool and a full-service spa. Saybrook Point Resort & Marina: Offers a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking.
How many pool hotels are there 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 The Old Field Vineyards, Sparkling Pointe 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.