Photo by Benny Goh

Hotels with Swimming Pools in Southold

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 Swimming Pools

Top Hotels with Swimming Pools in Southold

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 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, (437)
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 S$172
includes taxes & fees
17 Nov - 18 Nov
Hamlet Inn
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, (1007)
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 S$151
includes taxes & fees
23 Nov - 24 Nov
Quality Inn 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, (533)
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 S$264
includes taxes & fees
16 Dec - 17 Dec
The Harbor Front 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 S$281
includes taxes & fees
17 Nov - 18 Nov
North Fork Cottages & RV Resort
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 centre.
The price is S$107
includes taxes & fees
23 Nov - 24 Nov
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, (380)
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 S$172
includes taxes & fees
19 Nov - 20 Nov
The Bentley Hotel Southampton
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, (291)
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 S$116
includes taxes & fees
17 Nov - 18 Nov
Clinton Motel
Seasonal outdoor pool, open 9:00 AM to 8:00 PM, pool umbrellas
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
  • Pool loungers
8.8 out of 10, Excellent, (205)
Sparkling seasonal waters await at this boutique Hamptons bed & breakfast. Guests unwind poolside from May to September, enjoying loungers, umbrellas, and thoughtfully provided beach towels, all steps from renowned Wolffer Estates Vineyard.
The price is S$292
includes taxes & fees
17 Nov - 18 Nov
The Sagaponack
Outdoor pool
The Atlantic Hotel

The Atlantic Hotel

2.5 star property
Southampton
  • Outdoor pool
7.2 out of 10, Good, (966)
Splash into holiday 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 travellers.
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
"amenities clean room with turndown service "
michael 2-night trip
Posted 1 day 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 Sparkling Pointe and The Old Field 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: Provides buffet, an indoor pool and free self parking. Pier Blue Inn Old Saybrook - Essex: Offers 2 outdoor swimming 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 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 McCabe's Beach and Horton Lane Beach. Discover sights such as Sparkling Pointe, The Old Field Vineyards and Horton Point Park 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.