A calm lake with a forest in the background during sunset.

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Check availability on Southold Hotels with Swimming Pool

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug

Our top choices for Southold hotels with a pool

Seasonal outdoor pool, pool umbrellas, pool loungers

1. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (673 reviews)
  • cleanliness
    Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
The price is ₹38,434
₹52,085 total
includes taxes & fees
27 Aug - 28 Aug
Sound View Greenport
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

2. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (278 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is ₹45,664
₹60,676 total
includes taxes & fees
18 Aug - 19 Aug
Cliffside Resort Condominiums
Seasonal outdoor pool, pool umbrellas, pool loungers

3. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (95 reviews)
  • cleanliness
    Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
The price is ₹59,980
₹75,380 total
includes taxes & fees
31 Aug - 1 Sept
The Pridwin Hotel
Suite, 1 Bedroom, Terrace, Harbour View | Terrace/patio

4. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (634 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is ₹36,702
₹46,836 total
includes taxes & fees
5 Aug - 6 Aug
The Harbor Front Inn
Property amenity

5. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (63 reviews)
  • cleanliness
    Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
The price is ₹30,168
₹34,467 total
includes taxes & fees
13 Aug - 14 Aug
Shelter Island House
Seasonal outdoor pool

6. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (42 reviews)
The price is ₹58,380
₹66,699 total
includes taxes & fees
25 Aug - 26 Aug
North Fork Resort
Beach nearby

7. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very good, (43 reviews)
  • cleanliness
    Charming B&B features seasonal outdoor pool and free bicycle rentals for guests.
The price is ₹29,906
₹34,168 total
includes taxes & fees
4 Aug - 5 Aug
West Neck Guesthouse
Indoor pool, open 9:00 AM to 9:00 PM, pool umbrellas, pool loungers

8. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
  • cleanliness
    Plunge into pool paradise at this welcoming hotel with sun loungers and a relaxing indoor retreat.
The price is ₹11,271
₹12,961 total
includes taxes & fees
24 Aug - 25 Aug
Quality Inn Old Saybrook - Westbrook
Outdoor pool

9. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (653 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
The price is ₹48,555
₹55,474 total
includes taxes & fees
3 Aug - 4 Aug
Sag Harbor Inn
Seasonal outdoor pool

10. Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.6 out of 10, Excellent, (128 reviews)
  • cleanliness
    Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
The price is ₹22,150
₹32,158 total
includes taxes & fees
13 Aug - 14 Aug
Ocean View Terrace Inn
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

Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars

Top Southold Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"The place is really good but overpriced, in the room there is old furniture. Refrigerator doesn’t work well . The rooms can be more updated with price customers are paying . there is no coffee free for customers, every hotel offers coffee station . There was only one Starbucks spot - but honestly coffee tasted like water . Place is overpriced . The views , pool is excellent we enjoyed."
Irine 4-night trip
Posted 13 hours ago
Water's Edge Resort & Spa

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 5 places to stay with pools. During your visit, you can explore sights such as The Hamptons Beaches, and then kick back and relax poolside at one of the accommodation options in Southold that travellers like for their pools.
What are some accommodation options with pools in Southold?
The Shoals Suites and Slips: Offers buffet, a seasonal outdoor pool and free self parking. Vine & Sand: Features a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex: Hotel located near The Hamptons Beaches. Offers 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Sound View Greenport: Features a seasonal outdoor pool, an indoor pool and a private beach. The Atlantic Hotel: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
How many pool hotels are there in Southold?
Expedia has 5 hotels in Southold for your poolside break.
What is there to see and do in Southold?
Explore places such as The Hamptons Beaches while you're in the area. Make a point to visit attractions such as McCabe's Beach and Horton Lane Beach.
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.