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

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Check availability on Southold Hotels with a Pool

Tonight
Sep 12 - Sep 13
Tomorrow
Sep 13 - Sep 14
Next weekend
Sep 18 - Sep 20
In two weeks
Sep 25 - Sep 27

Our top choices for Southold hotels with a pool

A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A spacious room with wicker furniture, large windows, and a view of the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A coastal building with large windows, a deck, and a view of the sea at sunset.

1. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
₩356,396
₩445,500 total
includes taxes & fees
Oct 1 - Oct 2
Sound View Greenport
A rectangular swimming pool with a deck area, surrounded by lounge chairs and umbrellas.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
₩348,950
₩436,999 total
includes taxes & fees
Oct 4 - Oct 5
The Harbor Front Inn

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.
₩269,997
₩308,461 total
includes taxes & fees
Oct 4 - Oct 5
Shelter Island House
A poolside area with a hat and towel on a lounge chair.
A modern living room with a sofa, a dining table, and a kitchen area in the background.
A modern house with a deck, outdoor seating, and a fire pit.
A modern bathroom with a black bathtub, white sink, and shower area. There are framed pictures on the wall and a potted plant on the counter.

4. North Fork Resort

North Fork Resort
Greenport
₩431,056
₩492,482 total
includes taxes & fees
Sep 13 - Sep 14
North Fork Resort

5. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
₩389,999
₩565,911 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
A modern outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.
A hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.
A modern bathroom with a large mirror, wooden vanity, and a sink. There is a chair and a small table in the adjacent living area, with a sofa and a view of the outdoors.

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.
₩195,874
₩223,787 total
includes taxes & fees
Oct 12 - Oct 13
The Bentley Hotel Southampton
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.
A deck with outdoor seating, overlooking a body of water with a sunset view.
A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

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.
₩680,134
₩854,757 total
includes taxes & fees
Sep 13 - Sep 14
The Pridwin Hotel
A rectangular swimming pool with a fenced area, surrounded by trees and a concrete deck with white metal loungers.
A motel with a large parking lot and multiple rooms.
A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.
A parking lot with a building in the background.

8. 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 14 - Sep 15
Clinton Motel
A hotel room with a large bathtub, a desk with a lamp, a chair, and a bed with a red blanket.
A hotel lobby with a reception desk, a flat-screen TV mounted above a fireplace, and comfortable seating areas.
A tranquil park with a gazebo, a pond with a fountain, and a building in the background.
A deck with a table and chairs under a blue umbrella, surrounded by a wooden deck and a white fence.

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.
₩95,965
₩110,360 total
includes taxes & fees
Sep 27 - Sep 28
Econo Lodge Inn & Suites Old Saybrook Westbrook
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, with a grassy area and trees in the background.
A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.
A glass-top table with a vase of flowers, surrounded by white-covered chairs, in a bright indoor setting with plants and a fireplace in the background.
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

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.
₩170,048
₩219,795 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

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 hours ago
Water's Edge Resort & Spa
The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"This property is a lovely option if you want to be near to central Southampton but not in the middle of it. the room was really nicely appointed, they have a lovely grounds area near the pool, and a really nice pool deck with a pretty big heated pool. We really enjoyed the pool. Only negative is that It's located on a 2 lane highway without much close buy in the way of restaurants or other necessities; getting around was awkward and costly without a car. However, the place we stayed at was nice!"
Nancy 2-night trip
Posted 22 hours ago
The Atlantic Hotel
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Central to go any place within Long Island"
Eneida 4-night trip
Posted 1 day ago
Hyatt Place Long Island East End
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 10 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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