A coastal landscape with a sandy beach, calm waters, and a clear sky.

Hotels with Swimming Pool in Cutchogue, New York

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Cutchogue Hotels with Swimming Pool

Tonight
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Cutchogue 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 bar with wooden chairs and a small table, overlooking the sea.
A beach scene with a wooden structure, two wooden chairs, a campfire, and string lights.

1. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
P11,993
P15,489 total
includes taxes & fees
Nov 2 - Nov 3
Sound View Greenport
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 lounge area with a pool view, white furniture, and contemporary lighting fixtures.

2. 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.
P9,007
P10,291 total
includes taxes & fees
Oct 12 - Oct 13
The Bentley Hotel Southampton
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A spacious lobby with multiple seating areas, a kitchen area, and large windows providing natural light.
A spacious hallway with a fireplace, a large window, and a built-in shelving unit.
A waterfront property with a large house, multiple boats docked, and lush greenery.

3. 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.
P13,699
P15,651 total
includes taxes & fees
Nov 1 - Nov 2
Sag Harbor Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
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.

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
P10,077
P13,299 total
includes taxes & fees
Nov 1 - Nov 2
The Harbor Front Inn
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 modern hotel with a glass facade, a covered entrance, and a sign indicating it is a Hyatt Place.

5. 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.
P9,758
P11,149 total
includes taxes & fees
Nov 1 - Nov 2
Hyatt Place Long Island East End
Property amenity
Property amenity
Terrace/patio
Front of property - evening/night

6. 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.
P12,589
P14,382 total
includes taxes & fees
Oct 6 - Oct 7
Shelter Island House
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 beach with sand and sparse vegetation.
A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.

7. The Hampton Maid

The Hampton Maid
Hampton Bays
  • Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
P13,230
P15,115 total
includes taxes & fees
Oct 13 - Oct 14
The Hampton Maid
A rectangular swimming pool with metal ladders on both sides, surrounded by a stone wall and a fence.
A breakfast buffet with a bakery section and a display for how the food is prepared.
A modern bathroom with a white bathtub, grab bars, a showerhead, and a towel rack.
A hotel room with a gray sofa, a blue ottoman, a wooden desk, and a bed with white linens.

8. Holiday Inn Express & Suites Riverhead - Long Island by IHG

Holiday Inn Express & Suites Riverhead - Long Island by IHG
Riverhead
  • Seasonal splash and sun at Long Island's relaxing poolside retreat with loungers and umbrellas.
P9,445
P10,791 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Riverhead - Long Island by IHG
A modern bathroom with a marble sink, a toilet, and a large mirror.
A modern bar area with a mural of a woman in a flowing dress, wooden bar stools, and a seating area with yellow sofas and chairs.
A lobby with yellow upholstered chairs, a round wooden table, and a large abstract painting on the wall.
A two-story house with a front porch, a staircase, and a large glass window on the upper floor.

9. The Preston House & Hotel

The Preston House & Hotel
Riverhead
  • Sunrise splash sessions in the rooftop pool with local art exhibitions nearby.
P11,970
P13,675 total
includes taxes & fees
Nov 2 - Nov 3
The Preston House & Hotel
A swimming pool with a white fence, a table with chairs, and a building with a white picket fence in the background.
A living room area with a sofa, a dining table, and a separate queen bedroom.
A living room with a wooden entertainment center, a sofa, a coffee table, and a lamp.
A bedroom with a bed, bedside tables, a chair, a desk, and a bathroom visible through an open door.

10. Southampton Long Island Hotel

Southampton Long Island Hotel
Southampton
  • Luxurious poolside retreat with seasonal outdoor oasis and plush sun loungers, just minutes from Cooper's Beach in the Hamptons.
P9,946
P11,861 total
includes taxes & fees
Oct 6 - Oct 7
Southampton Long Island Hotel
View all properties

Choose what matters most at hotels with a pool in Cutchogue

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Cutchogue Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

8/10 Good
"My only complaint would be i wish there was a Keurig machine in the room instead of an espresso machine. Would definitely stay there again."
Fred 2-night trip
Posted 4 hours ago
The Atlantic Hotel
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Scenery was picture postcard perfect! Highly recommend balcony view from the main hotel Room service was excellent and the dining room staff and food were wonderful Only downside. There were no robes in the room and if you drank the bottled water, you were charged. Not really disclosed very well I'm actually planning on going back"
Billie 2-night trip
Posted 6 hours ago
Water's Edge Resort & Spa
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

10/10 Excellent
"Great stay. The hotel was clean and convenient. Highly recommend."
Bryan 1-night trip
Posted 21 hours ago
Hilton Garden Inn Riverhead
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"I had one night slp there every thing was amazing clean and good breakfast was so fresh and yummy"
Susan 1-night trip
Posted 2 days ago
Hyatt Place Long Island East End
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 5 days ago
Saybrook Point Resort & Marina
Budget Host East End

Budget Host East End

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

Frequently asked questions

What are some accommodations with pools in Cutchogue?
Pier Blue Inn Old Saybrook - Essex: Offers a seasonal outdoor pool, an indoor pool, and a private beach. Water's Edge Resort & Spa: Provides 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. The Atlantic Hotel: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Zey Hotel: Hotel, 3-minute walk from The Hamptons Beaches. Provides spa services, a seasonal outdoor pool, and a snack bar/deli.
What is there to see and do in Cutchogue?
Make a point to visit attractions like 8 Hands Farm. Discover sights such as Peconic Bay Winery, Bedell Cellars, and Pugliese Vineyards during your stay.
When is the best time to book a hotel with a pool in Cutchogue?
You may want to think about a place to stay that offers an outdoor pool if you plan to visit Cutchogue 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 visit during the coldest months of January, February, or March when the average temp is 38°F.

Explore a world of travel with Expedia