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

Hotels with Swimming Pools in Southold

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Check availability on Southold Hotels with Swimming Pools

Tonight
24 Oct - 25 Oct
Tomorrow
25 Oct - 26 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Southold hotels with a pool

A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.
A beach bar with wooden chairs and a small table, overlooking the sea.
A coastal building with a deck extending over the water, featuring large windows and a dining area.
A spacious room with wicker furniture, large windows, and a view of the sea.

1. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
S$272
includes taxes & fees
22 Nov - 23 Nov
Sound View Greenport
A swimming pool with a wooden deck, lounge chairs, and a fence.
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.
A bar area with wooden bar stools and a bookshelf.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
S$250
includes taxes & fees
24 Nov - 25 Nov
The Harbor Front Inn
Outdoor pool
Beach
Room
Terrace/patio

3. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
S$389
includes taxes & fees
12 Nov - 13 Nov
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 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.
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 outdoor seating area with a white sofa and a table, a sliding glass door, and a number '25' on the wall.

4. 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.
S$210
includes taxes & fees
31 Oct - 1 Nov
The Bentley Hotel Southampton
A poolside area with lounge chairs and yellow umbrellas.
A bedroom with a large bed, a window with curtains, a wall-mounted lamp, and a framed artwork.
A cozy interior with a bar area, seating, and a fireplace.
A modern living room with a sectional sofa, a wooden coffee table, and a large window providing a view of trees.

5. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
S$362
includes taxes & fees
26 Oct - 27 Oct
Oyster Estate
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A waterfront property with a large house, multiple boats docked, and lush greenery.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A hotel lobby with a sofa, chairs, tables, and a large window.

6. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
S$320
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
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 bathroom with a black bathtub, white sink, and shower area. There are framed pictures on the wall and a potted plant on the counter.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

7. North Fork Resort

North Fork Resort
Greenport
S$448
includes taxes & fees
25 Nov - 26 Nov
North Fork Resort
Property amenity
Terrace/patio
Property amenity
Bar (on property)

8. 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.
S$495
includes taxes & fees
31 Oct - 1 Nov
Shelter Island House
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A dining area with tables set for a meal, a fireplace, and a large mirror reflecting the room.
A spacious living room with a fireplace, comfortable seating, and large windows.

9. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
S$564
includes taxes & fees
22 Nov - 23 Nov
Faraway Sag Harbor
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.
A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.
A modern kitchen with a central island, a dining area with a black and white striped sofa, and a living area with a black leather couch.
A sign for 'The Atlantic Southampton' with a stylized logo and text.

10. The Atlantic Hotel

The Atlantic Hotel
Southampton
  • Splash into summer at this modern hotel with tennis courts and a seasonal pool for sunny relaxation.
S$188
includes taxes & fees
28 Oct - 29 Oct
The Atlantic 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

Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"clean room"
Susan 1-night trip
Posted 8 hours ago
Hyatt Place Long Island East End
Faraway Sag Harbor

Faraway Sag Harbor

8/10 Good
"Beautiful and charming hotel! Unfortunately the restaurant was only serving breakfast and not dinner, since we arrived off- season. However the restaurant was freezing due to the heating system not working so we had to go elsewhere in town for breakfast. Too bad because it was a lovely room with a harbor view. Our biggest disappointment by far was the coffee in the room and in the lobby. Nasty stuff! I have never tasted coffee this bad in any hotel (and we have been to many). First of all at this high- end price point per night, Faraway should be providing at least a Nespresso machine in each room for a decent morning cup of coffee instead of instant coffee packets which went out with Sanka like forty years ago. :( Then we thought that maybe the coffee urns on the bar in the common area would at least provide a half decent cup of coffee. Boy were we wrong! The fact that other filled cups of coffee which were left on the bar still full told us that other guests felt the same about the quality of coffee. Thank goodness for Goldbergs Bagel shop in town! Come on guys. If you want to be recognized as a high end getaway in an extremely wealthy part of Long Island, please find yourselves a better quality coffee source. Its not that hard these days. We speak for all true coffee lovers."
Joan 2-night trip
Posted 2 days ago
Faraway Sag Harbor
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"We were 4 girls and the room was two bedrooms and another bed also so it accommodated all of us. 😊"
Grace 1-night trip
Posted 5 days ago
The Atlantic Hotel

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: Features a seasonal outdoor pool, an indoor pool and a private beach. Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool and 2 bars. Water's Edge Resort & Spa: Features 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. Sound View Greenport: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Atlantic Hotel: Hotel, 3-minute walk from The Hamptons Beaches. Offers spa services, a seasonal outdoor pool and a snack bar/deli.
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?
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 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.

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