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

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Check availability on Southold Hotels with Pool

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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 scene with a wooden structure, two wooden chairs, a campfire, and string lights.
A spacious room with wicker furniture, large windows, and a view of the sea.
A beach bar with wooden chairs and a small table, overlooking 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.
฿6,003
฿7,815 total
includes taxes & fees
16 Nov - 17 Nov
Sound View Greenport
A swimming pool with a wooden deck, lounge chairs, and a fence.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.
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.

2. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
฿5,999
฿7,811 total
includes taxes & fees
2 Nov - 3 Nov
The Harbor Front Inn
A poolside area with lounge chairs and yellow umbrellas.
A wooden desk with drawers, a chair, a lamp, and a framed picture on the wall.
A wooden cabinet with a newspaper, a coffee maker, and a mug on top. There is a small stool and a window with blinds.
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.
฿7,541
฿9,501 total
includes taxes & fees
28 Oct - 29 Oct
Oyster Estate
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 hotel lobby with a sofa, chairs, tables, and a large window.
A waterfront property with a large house, multiple boats docked, and lush greenery.

4. 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.
฿7,340
฿8,386 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
Property amenity
Terrace/patio
Front of property – evening/night
Property amenity

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.
฿6,745
฿7,706 total
includes taxes & fees
19 Oct - 20 Oct
Shelter Island House
Outdoor pool
Beach
Terrace/patio
Room

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
฿5,665
฿10,190 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums
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 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.

7. North Fork Resort

North Fork Resort
Greenport
฿10,768
฿12,303 total
includes taxes & fees
18 Oct - 19 Oct
North Fork Resort
A pool area with umbrellas, potted plants, and a pathway leading to a building.
A cozy outdoor seating area with a brick fireplace, cushioned seating, and potted plants.
A hallway with dark wooden doors, a patterned carpet, and a decorative ceiling.
A spacious living room with a fireplace, comfortable seating, and large windows.

8. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
  • Dive into summer splendour at a tranquil pool retreat with chic cabanas and luxe loungers.
฿12,367
฿15,542 total
includes taxes & fees
16 Nov - 17 Nov
Faraway Sag Harbor
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.
A marina with boats docked, a globe sculpture, wicker furniture, and a bottle of wine on a table.
A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.

9. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
  • Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.
฿4,256
฿4,863 total
includes taxes & fees
3 Nov - 4 Nov
Hyatt Place Long Island East End
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 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 modern lounge area with a pool view, white furniture, and contemporary lighting fixtures.

10. 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.
฿4,793
฿5,476 total
includes taxes & fees
16 Nov - 17 Nov
The Bentley Hotel Southampton
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

8/10 Good
"Front desk staff provider typical Long Island hospitality… Just rude! You should send your people to the South for training for six months to get that chip off their shoulder."
shaun 3-night trip
Posted 3 hours ago
Hyatt Place Long Island East End
The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"This is actually a really great place to stay if you want something reasonable in the Hamptons. The rooms are clean and spacious and the grounds of the hotel are beautiful. I highly recommend!!!"
Constantine 1-night trip
Posted 8 hours ago
The Atlantic Hotel
Sound View Greenport

Sound View Greenport

10/10 Excellent
"The breakfast could have had a better choice."
Allen 1-night trip
Posted 3 days ago
Sound View Greenport

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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