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

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Check availability on Cutchogue Hotels with a Pool

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 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 coastal building with large windows, a deck, and a view of the sea at sunset.
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.
AED 641
AED 837 total
includes taxes & fees
3 Nov - 4 Nov
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.
AED 529
AED 604 total
includes taxes & fees
12 Oct - 13 Oct
The Bentley Hotel Southampton
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 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.

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.
AED 804
AED 919 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
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 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.

4. 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
3 Nov - 4 Nov
The Harbor Front Inn
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 bedroom with a large bed, a chandelier, and multiple windows.

5. The Hampton Maid

The Hampton Maid
Hampton Bays
  • Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
AED 777
AED 888 total
includes taxes & fees
13 Oct - 14 Oct
The Hampton Maid
Property amenity
Property amenity
Bar (on property)
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.
AED 739
AED 844 total
includes taxes & fees
4 Oct - 5 Oct
Shelter Island House
Outdoor pool
Terrace/patio
Room
Room

7. 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
A poolside area with lounge chairs and yellow umbrellas.
A hotel room with a bed, pillows, a lamp, a wall art piece, and a nightstand.
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.

8. 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
A poolside area with lounge chairs, a table with food and drinks, and a pool.
A breakfast buffet with various food items and beverages.
A beach chair with a towel labeled "CANOE PLACE" and a wicker basket with bottles and a container on the sand.
A person riding a bicycle under a striped awning with a logo, in front of a building with large windows and a white facade.

9. Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
Hampton Bays
  • Dive into pool-side luxury at this Hamptons retreat where massages and seasonal swimming create a waterfront escape period.
AED 1,640
AED 1,986 total
includes taxes & fees
21 Oct - 22 Oct
Canoe Place Inn and Cottages
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 dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.
A marina with boats docked, a fire feature, and outdoor seating with a bottle and glasses.

10. 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.
AED 573
AED 655 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Long Island East End
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
"Byłoby miło gdyby w pokoju oprócz kawy była także herbata."
Wojciech 1-night trip
Posted 1 day ago
The Atlantic Hotel
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 2 days ago
Saybrook Point Resort & Marina
Budget Host East End

Budget Host East End

8/10 Good
"Staff"
Harvey 2-night trip
Posted 11 days 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.