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

Find Hotels with a Pool in Southold, NY

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Check availability on Southold Hotels with a Pool

Tonight
Sep 15 - Sep 16
Tomorrow
Sep 16 - Sep 17
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Southold hotels with a pool

Seasonal outdoor pool, pool umbrellas, sun loungers
Private beach, sun loungers, beach umbrellas, beach towels
Terrace/patio
Resort view

1. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
₩357,658
₩447,075 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers
Studio (Suite, King) | Frette Italian sheets, premium bedding, down comforters, pillowtop beds
Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio
View from room

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
₩338,068
₩424,692 total
includes taxes & fees
Oct 15 - Oct 16
The Harbor Front Inn
Seasonal outdoor pool
Balcony
Shower, free toiletries, towels, soap
Cottage, 2 Bedrooms, Patio | Living room | Flat-screen TV

3. North Fork Resort

North Fork Resort
Greenport
₩431,056
₩492,482 total
includes taxes & fees
Sep 21 - Sep 22
North Fork Resort
Property amenity
Front of property - evening/night
Terrace/patio
Bar (on property)

4. Shelter Island House

Shelter Island House
Shelter Island Heights
  • Relaxing seasonal pool oasis beckons at this Shelter Island retreat, where a poolside bar enhances sun-drenched afternoons.
₩269,997
₩308,461 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas
Private beach
Condo | 2 bedrooms, iron/ironing board, WiFi (free), individually decorated
Condo | Terrace/patio

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
₩387,615
₩562,453 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
1 bedroom, premium bedding, down comforters, in-room safe
Reception
Suite, 1 Bedroom (2 Queen beds, 1st Floor) | 1 bedroom, premium bedding, down comforters, in-room safe

6. The Bentley Hotel Southampton

The Bentley Hotel Southampton
Southampton
  • Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
₩200,142
₩262,321 total
includes taxes & fees
Oct 5 - Oct 6
The Bentley Hotel Southampton
Seasonal outdoor pool
Cribs (free), rollaway beds (surcharge), WiFi (free), bed sheets
Property grounds
Free self parking

7. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
₩104,645
₩120,342 total
includes taxes & fees
Sep 16 - Sep 17
Clinton Motel
Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas
Lobby lounge
Restaurant
Double Room | Terrace/patio

8. Hamlet Inn

Hamlet Inn
Southampton
  • Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
₩170,650
₩220,573 total
includes taxes & fees
Sep 27 - Sep 28
Hamlet Inn
Seasonal outdoor pool, open 9:00 AM to 8:30 PM, pool umbrellas
Restaurant
Bay King | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
Exterior

9. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
₩463,144
₩583,534 total
includes taxes & fees
Oct 5 - Oct 6
Oyster Estate
Seasonal outdoor pool, pool umbrellas, sun loungers
Terrace/patio
Premium bedding, iron/ironing board, WiFi (free), individually furnished
Private beach, sun loungers, beach umbrellas, beach towels

10. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
  • Splash into coastal luxury at this beachfront hotel with a seasonal pool, spa, and private beach access.
₩810,730
₩1,018,882 total
includes taxes & fees
Sep 16 - Sep 17
The Pridwin Hotel
View all properties

Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Southold Hotel Reviews

Sound View Greenport

Sound View Greenport

10/10 Excellent
"Great place on the water. Piano Bar is nice; good food & drink. All the staff was very friendly and helpful."
Joseph 3-night trip
Posted 7 hours ago
Sound View Greenport
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Friendly staff, comfortable and clean room. Modern and bright."
Danielle 1-night trip
Posted 11 hours ago
Hilton Garden Inn Riverhead
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Miguel 2-night trip
Posted 2 days ago
Faraway Sag Harbor
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."
Michael 1-night trip
Posted 3 days ago
Water's Edge Resort & Spa

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 5 places to stay with pools. While you're visiting, you can explore sights such as The Hamptons Beaches, and then relax and unwind poolside at one of the accommodations in Southold that travelers like for their pools.
What are some accommodations with pools in Southold?
The Shoals Suites and Slips: Provides a private beach, a seasonal outdoor pool, and 2 bars. Pier Blue Inn Old Saybrook - Essex: Features a seasonal outdoor pool, an indoor pool, and a private beach. Sound View Greenport: Offers 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Water's Edge Resort & Spa: Provides free self parking, a seasonal outdoor pool, and complimentary wireless internet access. The Atlantic Hotel: Hotel, 3-minute walk from The Hamptons Beaches. Features spa services, a seasonal outdoor pool, and a snack bar/deli.
How many pool hotels should I expect to find in Southold?
Expedia has 5 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 Sannino's Bella Vita Vineyard 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.

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