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

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Check availability on Cutchogue Hotels with Pool

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Cutchogue 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 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.
฿6,003
฿7,815 total
includes taxes & fees
16 Nov - 17 Nov
Sound View Greenport
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, with a building in the background.
A hotel lobby with a sofa, chairs, tables, and a large window.
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.

2. 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
15 Nov - 16 Nov
Sag Harbor Inn
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 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.

3. 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
A swimming pool with a wooden deck, lounge chairs, and a fence.
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.
A hotel room with a bed, a blue sofa, a wicker chair, a small table with a vase, and a lamp.

4. 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
15 Nov - 16 Nov
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 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.
A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.

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.
฿4,272
฿4,880 total
includes taxes & fees
3 Nov - 4 Nov
Hyatt Place Long Island East End
A rectangular swimming pool with metal ladders on both sides, surrounded by a stone wall and a fence.
A coffee station with two coffee machines and a variety of coffee pods and cups.
A hotel room with a gray sofa, a blue ottoman, a wooden desk, and a bed with white linens.
A breakfast buffet area with various food stations, including yogurt, eggs, and hot water.

6. 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.
฿4,272
฿4,880 total
includes taxes & fees
3 Nov - 4 Nov
Holiday Inn Express & Suites Riverhead - Long Island by IHG
A swimming pool with lounge chairs and a table, surrounded by greenery and buildings.
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.
A bedroom with a large bed, a chandelier, and multiple windows.

7. The Hampton Maid

The Hampton Maid
Hampton Bays
  • Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
฿7,088
฿8,098 total
includes taxes & fees
26 Oct - 27 Oct
The Hampton Maid
A modern bathroom with a marble sink, a toilet, and a large mirror.
A two-story house with a front porch, a staircase, and a large glass window on the upper floor.
A lobby with yellow upholstered chairs, a round wooden table, and a large abstract painting on the wall.
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.

8. The Preston House & Hotel

The Preston House & Hotel
Riverhead
  • Sunrise splash sessions in the rooftop pool with local art exhibitions nearby.
฿8,541
฿9,758 total
includes taxes & fees
2 Nov - 3 Nov
The Preston House & Hotel
Property amenity
Terrace/patio
Front of property – evening/night
Bar (on property)

9. 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
28 Oct - 29 Oct
Shelter Island House
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 covered patio area with outdoor seating, a potted plant, and a well-maintained lawn.
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.
฿5,348
฿6,378 total
includes taxes & fees
18 Oct - 19 Oct
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

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 4 hours ago
The Atlantic Hotel
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Property was amaculate and a big shout out to Joe at the front desk. Made our stay wonderful!!!"
Timothy 2-night trip
Posted 8 hours ago
Hyatt Place Long Island East End
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 are some accommodation options 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 such as 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 with an outdoor swimming pool if you plan to visit Cutchogue 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 are visiting during the coldest months of January, February or March, when the average temp is 3°C.

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