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 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Southold hotels with a pool

Pool
Beach
Restaurant
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.
NT$8,381
NT$10,477 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport
Pool
View from room
Studio (Suite, King)
Suite, 1 Bedroom, Terrace, Harbor View | Terrace/patio

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
NT$8,206
NT$10,277 total
includes taxes & fees
Oct 4 - Oct 5
The Harbor Front Inn
Property amenity
Property amenity
Bar (on property)
Terrace/patio

3. 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.
NT$6,349
NT$7,254 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
Pool
Balcony
Cottage, 2 Bedrooms, Patio | Living room
Bathroom

4. North Fork Resort

North Fork Resort
Greenport
NT$10,110
NT$11,551 total
includes taxes & fees
Sep 13 - Sep 14
North Fork Resort
Outdoor pool
Condo
Condo
Beach

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
NT$9,115
NT$13,227 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
Pool
Room
Reception
Room

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.
NT$4,575
NT$6,015 total
includes taxes & fees
Oct 5 - Oct 6
The Bentley Hotel Southampton
Pool
Beach
Room
Terrace/patio

7. 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.
NT$15,952
NT$20,048 total
includes taxes & fees
Sep 14 - Sep 15
The Pridwin Hotel
Pool
Parking
Room
Room

8. Clinton Motel

Clinton Motel
Clinton
  • Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.
NT$2,454
NT$2,823 total
includes taxes & fees
Sep 14 - Sep 15
Clinton Motel
Room
Pool
Exterior
Exterior

9. Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
Old Saybrook
  • Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodations.
NT$2,257
NT$2,595 total
includes taxes & fees
Sep 27 - Sep 28
Econo Lodge Inn & Suites Old Saybrook Westbrook
Pool
Double Room | Terrace/patio
Restaurant
Lobby lounge

10. 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.
NT$3,999
NT$5,169 total
includes taxes & fees
Sep 13 - Sep 14
Hamlet Inn
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

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"it was a clean bright comfortable room .Super cozy bed and pillows ,wonderful jacuzzi tub! A nice touch with an espresso machine in the room! Parking was easy and close to everything needed."
Amy 1-night trip
Posted 2 hours ago
The Atlantic Hotel
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

8/10 Good
"I was traveling through CT, stopped here overnight...hotel is conveniently located right off the highway. Very clean, very comfortable bed...my room could have used more lighting... namely, a lamp on the desk to get some work done after dark. Otherwise, this Quality Inn room was just right."
Joy 1-night trip
Posted 14 hours ago
Quality Inn Old Saybrook - Westbrook
Hyatt Place Long Island East End

Hyatt Place Long Island East End

8/10 Good
"Good location. Rooms were good size, friendly staff and excellent breakfast. I was with my wife only but saw many families with children enjoying the pools. This was my second stay at The Hyatt and will go again.Location is very good as you are 10 to 15 minutes away fron the Wine trail."
Stanley 1-night trip
Posted 17 hours ago
Hyatt Place Long Island East End
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Bartender was great. I got in late a wanted a beer so she took her time cleaning up so i could relax and have a beer! Great service."
Gerald 1-night trip
Posted 5 days ago
Hilton Garden Inn Riverhead
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Faraway has been renovated Beautifully. The food has improved since Baron's Cove. The pool would benefit improving service and perhaps combining the food / drinks servers and pool attendants. In addition since we have been guests of the older Hotel, Baron's Cove for 16 years it would have been meaningful to have the new staff welcome guests and perhaps give a priority rate or welcome massage etc."
Claudia 3-night trip
Posted 9 days ago
Faraway Sag Harbor

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: Offers a private beach, a seasonal outdoor pool, and 2 bars. Sound View Greenport: Features 2 outdoor tennis courts, a seasonal outdoor pool, and free self parking. Pier Blue Inn Old Saybrook - Essex: Offers a seasonal outdoor pool, an indoor pool, and a private beach. The Atlantic Hotel: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Water's Edge Resort & Spa: Offers 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 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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