Hotels with a Pool in Southold

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Top 5 Hotels with a Pool in Southold at a glance

Quality Inn Old Saybrook - Westbrook — 2.5-star hotel in Old Saybrook. Guest rating: 7.8/10 — Good.
The Harbor Front Inn — 3.5-star hotel in Greenport. Guest rating: 8.8/10 — Excellent.
Shelter Island House — 3.5-star hotel in Shelter Island Heights. Guest rating: 8.4/10 — Very Good.
Clinton Motel — 2.5-star hotel in Clinton. Guest rating: 8.6/10 — Excellent.
Sag Harbor Inn — 3.5-star hotel in Sag Harbor. Guest rating: 9.4/10 — Exceptional.

Hotels with a Pool in Southold

An indoor swimming pool with a tiled floor, a pool ladder, and a ceiling with a grid pattern.

A hallway with a blue reception desk, framed artwork on the walls, and a wooden door with a men's restroom sign.

A spacious lobby with two sofas, a coffee table, and a flat-screen TV mounted on the wall.

A hotel lobby with a reception desk, two sofas, a coffee table, and a carpeted floor.

Quality Inn Old Saybrook - Westbrook

Old Saybrook

Indoor pool
Pool loungers

$101

$116 total

includes taxes & fees

Sep 27 - Sep 28

A swimming pool with lounge chairs and a wooden deck.

A balcony with a view of a dock and a boat, a table with a basket of pastries, and a chair.

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.

The Harbor Front Inn

Greenport

Pool loungers
Near the beach

$276

$367 total

includes taxes & fees

Sep 10 - Sep 11

Shelter Island House

Shelter Island Heights

Near the beach

$316

$361 total

includes taxes & fees

Sep 7 - Sep 8

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 two beds, a desk, a chair, a window with curtains, and two wall-mounted lamps.

A hotel room with a large bed, two bedside tables, a desk with chairs, a TV, and a small table with flowers.

Clinton Motel

Clinton

Pool
Free parking
Free WiFi
Air conditioning
24/7 front desk

$78

$90 total

includes taxes & fees

Sep 2 - Sep 3

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 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.

Sag Harbor Inn

Sag Harbor

Outdoor pool
Near the beach

$301

$344 total

includes taxes & fees

Sep 21 - Sep 22

A pool area with lounge chairs and umbrellas, a swimming pool, and a view of the sea.

A balcony with a view of the ocean, a white railing, and two white chairs with blue cushions.

A formal dining room with multiple tables and chairs, large windows with a city view, and a decorative carpet.

A large hotel with a spacious outdoor patio area, multiple dining tables, and umbrellas.

Water's Edge Resort & Spa

Westbrook Center

Indoor pool
Pool loungers
On private beach
Hot tub

$220

$270 total

includes taxes & fees

Sep 15 - Sep 16

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a view of the sea.

A beach with rows of white lounge chairs and umbrellas, a wooden table with a drink, and a person walking along the shore.

A deck with outdoor seating, overlooking a body of water with a sunset view.

The Pridwin Hotel

Shelter Island Heights

Poolside bar
Pool loungers
On private beach
Full-service spa

$535

$672 total

includes taxes & fees

Sep 7 - Sep 8

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.

An outdoor patio with wicker furniture, a fire pit, string lights, and potted plants.

A modern bar area with a round glass table, leather chairs, and a bar counter with stools.

A modern living room with a sofa, coffee table, and a dining area with a bar.

Residence Inn by Marriott New York Long Island East End

Riverhead

Indoor pool
2 hot tubs

$206

$235 total

includes taxes & fees

Sep 7 - Sep 8

A swimming pool with lounge chairs and umbrellas, a fence, and a sunset view.

A coastal building with large windows, a deck, and a view of the sea at sunset.

A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

A seaside restaurant with outdoor seating, a deck, and a view of the ocean.

Sound View Greenport

Greenport

Poolside bar
Pool loungers
On private beach

$72

$168 total

includes taxes & fees

Sep 30 - Oct 1

A cozy living room with a wooden floor, a round dining table, a sofa, and a bookshelf.

A bedroom with a bed, bedside tables, a nightstand, a lamp, a painting, a robe, and a bathroom door.

A cozy interior with a bar area, seating, and a fireplace.

A cozy interior with a wooden bench, a sofa, and a bar area.

Oyster Estate

Greenport

Pool loungers
Hot tub

$340

$428 total

includes taxes & fees

Sep 14 - Sep 15

A swimming pool with lounge chairs and a table, surrounded by greenery and buildings.

A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.

A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

A beach with sand and sparse vegetation.

The Hampton Maid

Hampton Bays

Near the beach

$261

$298 total

includes taxes & fees

Sep 8 - Sep 9

A poolside area with lounge chairs, umbrellas, and a view of boats in the background.

A modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

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.

Hyatt Place Long Island East End

Riverhead

Outdoor pool
Indoor pool
Poolside bar

$203

$232 total

includes taxes & fees

Sep 9 - Sep 10

An indoor swimming pool with clear blue water, wooden beams, and lounge chairs.

A two-story Victorian-style house with a balcony, a porch, and a small tower.

An aerial view of a marina with boats docked, a parking lot, and buildings with a waterfront view.

A marina at sunset with boats docked, a fire feature on the deck, and a chair.

Saybrook Point Resort & Marina

Old Saybrook Center

2 outdoor pools
Indoor pool
Pool loungers
Near the beach
Hot tub

$369

$459 total

includes taxes & fees

Sep 3 - Sep 4

A rectangular swimming pool with metal ladders on both sides, surrounded by a stone wall and a fence.

A Holiday Inn Express hotel with a stone facade, multiple windows, and a covered entrance area.

A Holiday Inn Express hotel with a stone facade, large windows, and a covered entrance.

A gym with treadmills, elliptical machines, a bench, and a rack of dumbbells.

Holiday Inn Express & Suites Riverhead - Long Island by IHG

Riverhead

Pool loungers

$206

$235 total

includes taxes & fees

Sep 8 - Sep 9

An indoor swimming pool with tiled flooring, metal pool ladders, and white chairs around the perimeter.

A patio area with wicker furniture, a stone fire pit, and candles.

A modern bar area with a long counter, bar stools, and a television mounted above.

A modern hotel with a covered entrance, large windows, and a well-maintained garden.

Hilton Garden Inn Riverhead

Riverhead

Outdoor pool
Indoor pool
Pool loungers
Hot tub

$155

$177 total

includes taxes & fees

Sep 13 - Sep 14

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.

The Bentley Hotel Southampton

Southampton

Pool loungers
Near private beach

$160

$208 total

includes taxes & fees

Sep 15 - Sep 16

A pool area with lounge chairs and a covered seating area, surrounded by greenery and a view of neighboring houses.

A bedroom with a bed, a desk, a chair, a window with a view of trees and a body of water.

An outdoor seating area with Adirondack chairs and a table, surrounded by American flags and flowers, with a view of houses and a body of water in the background.

A house with a dark blue exterior, a white porch railing, and a red door.

Ocean View Terrace Inn

Hampton Bays

On the beach

$151

$233 total

includes taxes & fees

Sep 3 - Sep 4

Cliffside Resort Condominiums

Greenport

Pool loungers
On private beach

$340

$478 total

includes taxes & fees

Sep 8 - Sep 9

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 house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.

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.

Hamlet Inn

Southampton

Pool loungers
Near private beach

$144

$186 total

includes taxes & fees

Sep 27 - Sep 28

A bar area with multiple screens displaying content, a variety of bottles on shelves, and several bar stools.

A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

An outdoor dining area with brick walls, tables, and chairs.

A clear blue pool with lounge chairs and a stone wall in the background.

Hotel Indigo Long Island - East End by IHG

Riverhead

Pool loungers

$203

$232 total

includes taxes & fees

Sep 27 - Sep 28

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Discover your perfect hotel with a pool in Southold

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Top landmarks in Southold

Sparkling Pointe

8.8/10 (11 reviews)

Travelers might want a tour of Sparkling Pointe, just one of the places to visit, and located 1 mi (1.6 km) from central Southold.

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Croteaux Vineyards

10.0/10 (12 reviews)

Travelers might want a tour of Croteaux Vineyards, just one of the places to visit, and located 1.5 mi (2.4 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Mattebella Vineyards or Corey Creek Winery, both within a short walk.

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Sannino's Bella Vita Vineyard

9.6/10 (4 reviews)

Travelers might want a tour of Sannino's Bella Vita Vineyard, just one of the places to visit, and located 2.2 mi (3.5 km) from central Southold. If you enjoy your tour, head to Osprey's Dominion, just a short walk away.

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Horton Point Park

9.4/10 (3 reviews)

Horton Point Park is 1.7 mi (2.8 km) from central Southold, why not stop by during your stay. Want to stretch your legs some more? Head to Goldsmith's Inlet Park, located nearby.

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Horton Lane Beach

9.0/10 (4 reviews)

If you can't wait to get to the beach, you might enjoy a trip to Horton Lane Beach located 1.6 mi (2.6 km) from central Southold. If you want to continue walking by the waves, head to McCabe's Beach located nearby.

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Corey Creek Winery

9.6/10 (5 reviews)

Travelers might want a tour of Corey Creek Winery, just one of the places to visit, and located 1.7 mi (2.7 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Croteaux Vineyards or Mattebella Vineyards, both within a short walk.

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McCabe's Beach

When the beach is calling your name, you might want to head down to McCabe's Beach, located 1.6 mi (2.5 km) from central Southold. If you want to continue walking by the waves, head to Horton Lane Beach located nearby.

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Mattebella Vineyards

8.0/10 (4 reviews)

Travelers might want a tour of Mattebella Vineyards, just one of the places to visit, and located 1.4 mi (2.3 km) from central Southold. Why not take a stroll along the beaches and watch the sunset while you're here? If you enjoy your tour, head to Croteaux Vineyards or Corey Creek Winery, both within a short walk.

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