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
14 Sep - 15 Sep
Tomorrow
15 Sep - 16 Sep
This weekend
18 Sep - 20 Sep
Next weekend
25 Sep - 27 Sep

Our top choices for Cutchogue hotels with a pool

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.

1. 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.
฿4,792
฿5,475 total
includes taxes & fees
13 Oct - 14 Oct
The Bentley Hotel Southampton
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, with a grassy area and trees in the background.
A spacious living room with a white sofa, a coffee table, and a fireplace. There are large windows offering a view of the outdoors.
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.
A room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.

2. Hamlet Inn

Hamlet Inn
Southampton
  • Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
฿4,189
฿5,415 total
includes taxes & fees
27 Sept - 28 Sept
Hamlet Inn
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 seaside restaurant with outdoor seating, a deck, and a view of the ocean.
A coastal building with large windows, a deck, and a view of the sea at sunset.

3. Sound View Greenport

Sound View Greenport
Greenport
  • Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
฿8,780
฿10,975 total
includes taxes & fees
1 Oct - 2 Oct
Sound View Greenport
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden fence and trees.
A sign for 'The Atlantic Southampton' with a stylized logo and text.
A modern kitchen with a central island, a dining area with a black and white striped sofa, and a living area with a black leather couch.
A hotel room with a bed, bedside tables, a desk with chairs, a sofa, a window with curtains, and a door leading outside.

4. The Atlantic Hotel

The Atlantic Hotel
Southampton
  • Splash into summer at this modern hotel with tennis courts and a seasonal pool for sunny relaxation.
฿3,941
฿5,329 total
includes taxes & fees
1 Oct - 2 Oct
The Atlantic Hotel
A pool area with lounge chairs and a covered seating area, surrounded by greenery and a view of neighboring houses.
Two Adirondack chairs facing a beach with a clear view of the sea and a distant island.
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 bedroom with a bed, a desk, a chair, a window with a view of trees and a body of water.

5. Ocean View Terrace Inn

Ocean View Terrace Inn
Hampton Bays
  • Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
฿4,532
฿7,122 total
includes taxes & fees
21 Sept - 22 Sept
Ocean View Terrace Inn
A swimming pool with lounge chairs and a table, surrounded by greenery and buildings.
A beach with sand and sparse vegetation.
A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.
A bedroom with a large bed, a chandelier, and multiple windows.

6. The Hampton Maid

The Hampton Maid
Hampton Bays
  • Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
฿6,990
฿7,986 total
includes taxes & fees
13 Oct - 14 Oct
The Hampton Maid
A swimming pool with a child on a pink and white inflatable float.
A dining area with wicker chairs, a glass table, and a flat-screen TV mounted on the wall.
A hotel room with two beds, a desk, a coffee maker, and a view of greenery through the window.
A stone fireplace with a built-in bench, a window with a view of trees, and a stone floor.

7. Hampton's Vacation Inn

Hampton's Vacation Inn
Hampton Bays
  • Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.
฿4,090
฿4,673 total
includes taxes & fees
17 Sept - 18 Sept
Hampton's Vacation Inn
A conservatory with a sofa, chairs, a small table, and a view of houses.
A sunlit room with a glass ceiling, a sofa, chairs, a table, and a view of the outside.
A bedroom with a bed, two bedside tables, a window with curtains, a wall-mounted lamp, and a framed picture.
A residential property with a covered patio, a gravel driveway, and a fenced yard.

8. The Penny Lane

The Penny Lane
Hampton Bays
  • Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.
฿5,327
฿6,086 total
includes taxes & fees
1 Oct - 2 Oct
The Penny Lane
A rectangular swimming pool with a deck area, surrounded by lounge chairs and umbrellas.
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.

9. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
฿8,299
฿10,425 total
includes taxes & fees
15 Oct - 16 Oct
The Harbor Front Inn
A poolside area with lounge chairs, umbrellas, and a view of boats in the background.
A dining area with wooden paneling, a patterned floor, and a view of outdoor seating through large windows.
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.

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.
฿5,619
฿6,419 total
includes taxes & fees
13 Oct - 14 Oct
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

Sound View Greenport

Sound View Greenport

10/10 Excellent
"The rooms were exceptionally clean, and the staff was friendly, attentive, and professional throughout our stay. However, the breakfast options were average and could definitely be improved. Overall, it was a pleasant experience, and I would still highly recommend this hotel."
Ragip 1-night trip
Posted 1 hour ago
Sound View Greenport
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

8/10 Good
"Nice value hotel"
Henry 2-night trip
Posted 5 hours ago
Hilton Garden Inn Riverhead
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"Excellent hotel. Comfortable beds. Nice decorated. Very professional and friendly staff."
Miguel 2-night trip
Posted 23 hours ago
Faraway Sag Harbor
Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct ."
Michael 1-night trip
Posted 2 days ago
Water's Edge Resort & Spa

Frequently asked questions

What are some accommodation options with pools in Cutchogue?
Sound View Greenport: Features a private beach, a seasonal outdoor pool and 2 bars. Pier Blue Inn Old Saybrook - Essex: Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Atlantic Hotel: Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access.
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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