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
30 Sep - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 spacious room with wicker furniture, large windows, and a view of the sea.
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.
AED 786
AED 1,003 total
includes taxes & fees
1 Nov - 2 Nov
Sound View Greenport
Pool
A rooftop terrace with lounge chairs, a wooden table, and a view of the landscape.
A neatly arranged hotel room with a bed, two bedside tables with lamps, a window with curtains, and two framed artworks on the wall.
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.
AED 556
AED 740 total
includes taxes & fees
1 Nov - 2 Nov
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A wooden shower enclosure with a tiled wall, a showerhead, and a toilet visible through the door.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.

3. Oyster Estate

Oyster Estate
Greenport
  • Dive into summer vibes at this hip pool escape where loungers beckon and relaxation flows freely.
AED 955
AED 1,203 total
includes taxes & fees
1 Nov - 2 Nov
Oyster Estate
Outdoor pool
Terrace/patio
Beach
Room

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
AED 621
AED 1,117 total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums
Property amenity
Terrace/patio
Bar (on property)
Front of property - evening/night

5. 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.
AED 739
AED 844 total
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House
A poolside area with a hat and towel on a lounge chair.
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 modern house with a deck, outdoor seating, and a fire pit.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.

6. North Fork Resort

North Fork Resort
Greenport
AED 946
AED 1,081 total
includes taxes & fees
4 Oct - 5 Oct
North Fork Resort
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A hotel lobby with a sofa, chairs, tables, and a large window.

7. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
  • Swim into serenity at this charming Sag Harbor retreat with a seasonal outdoor pool and balcony views.
AED 804
AED 919 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
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 cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendor at a tranquil pool retreat with chic cabanas and luxe loungers.
AED 1,537
AED 1,932 total
includes taxes & fees
1 Nov - 2 Nov
Faraway Sag Harbor
A pool area with lounge chairs and umbrellas, a mural on the wall, and a clear view of the sky.
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.
A modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

9. 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.
AED 461
AED 632 total
includes taxes & fees
7 Oct - 8 Oct
The Bentley Hotel Southampton
A swimming pool with lounge chairs and umbrellas, surrounded by a forested area.
A bathtub surrounded by candles and flower petals.
Beach
A bedroom with two beds, a ceiling fan, a large window, and a view of greenery outside.

10. A Room At The Beach

A Room At The Beach
Bridgehampton
  • Soak up sunshine and serene vibes at this Hamptons motel with a stylish outdoor pool.
AED 1,088
AED 1,243 total
includes taxes & fees
4 Oct - 5 Oct
A Room At The Beach
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Choose what matters most at hotels with a pool in Southold

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Southold Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

8/10 Good
"The staff are very welcoming. A small point but the hot water in the bathroom is just warm and takes a time to arrive...."
David 2-night trip
Posted 11 hours ago
Saybrook Point Resort & Marina
Budget Host East End

Budget Host East End

8/10 Good
"Staff"
Harvey 2-night trip
Posted 9 days ago
Budget Host East End

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: 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 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.