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
Oct 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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 beach bar with wooden chairs and a small table, overlooking 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.
₩256,969
₩331,866 total
includes taxes & fees
Nov 2 - Nov 3
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 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.

2. 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.
₩293,517
₩335,343 total
includes taxes & fees
Nov 1 - Nov 2
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 hotel room with two beds, a wall art piece with the text "GOOD DREAMS START HERE", and a pink abstract wall design.

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.
₩191,657
₩218,968 total
includes taxes & fees
Oct 28 - Oct 29
The Bentley Hotel Southampton
A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a view of boats.
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.

4. The Harbor Front Inn

The Harbor Front Inn
Greenport
  • Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
₩239,907
₩312,372 total
includes taxes & fees
Nov 2 - Nov 3
The Harbor Front Inn
A swimming pool with lounge chairs and a table, surrounded by greenery and buildings.
A bedroom with a large bed, a chandelier, and multiple windows.
A modern kitchen with a central island, bar stools, pendant lighting, and a seating area with a sofa and coffee table.
A two-story house with a windmill on the roof, a balcony, and three Adirondack chairs in the front yard.

5. The Hampton Maid

The Hampton Maid
Hampton Bays
  • Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
₩283,465
₩323,858 total
includes taxes & fees
Oct 13 - Oct 14
The Hampton Maid
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 globe sculpture, wicker furniture, and a bottle of wine on a table.

6. 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.
₩179,595
₩205,187 total
includes taxes & fees
Nov 3 - Nov 4
Hyatt Place Long Island East End
Property amenity
Front of property - evening/night
Terrace/patio
Bar (on property)

7. 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.
₩269,727
₩308,152 total
includes taxes & fees
Oct 12 - Oct 13
Shelter Island House
Outdoor pool
Room
Terrace/patio
Beach

8. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
  • Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
₩226,531
₩407,506 total
includes taxes & fees
Nov 1 - Nov 2
Cliffside Resort Condominiums
A poolside area with a hat and towel on a lounge chair.
A rustic cabin with a wooden exterior, a front porch, and a staircase leading to the entrance.
A modern bathroom with a black bathtub, white sink, and shower area. There are framed pictures on the wall and a potted plant on the counter.
A modern house with a deck, outdoor seating, and a fire pit.

9. North Fork Resort

North Fork Resort
Greenport
₩357,045
₩407,925 total
includes taxes & fees
Oct 12 - Oct 13
North Fork Resort
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, with a grassy area and trees in the background.
A house with a covered porch, a garden with various plants and flowers, and a 'OPEN' sign on the window.
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 room with a wicker sofa, a small table with a potted plant, and a bed with a wooden ladder.

10. 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.
₩266,980
₩345,090 total
includes taxes & fees
Nov 9 - Nov 10
Hamlet Inn
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

Budget Host East End

Budget Host East End

10/10 Excellent
"La habitación estaba limpia, el baño también. Las camas talvez deberían ser más firmes, pero por lo demás la estadía en el hotel estuvo muy cómoda"
Juan 2-night trip
Posted 3 hours ago
Budget Host East End
The Hampton Maid

The Hampton Maid

10/10 Excellent
"Beautiful property. Lovely rooms."
Meredith 1-night trip
Posted 5 hours ago
The Hampton Maid
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"We changed our plans and spent all three afternoons at the spa and pool because it was so relaxing and lovely. The outdoor pool overlooked the marina and the indoor pool, sauna and whirpool helped invigorate us. The duck and risotto at the restaurant was excellent. The staff was incredibly helpful and attentive. We will be back again."
Leslie 2-night trip
Posted 7 hours ago
Saybrook Point Resort & Marina
Hilton Garden Inn Riverhead

Hilton Garden Inn Riverhead

8/10 Good
"Staff were very helpful, they printed some documents for me at the front desk. And, my room had reading lights over the bed. May not matter to most, but those lights are great for those of us who like to read in bed."
Darla 1-night trip
Posted 1 day ago
Hilton Garden Inn Riverhead
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"We were pleased with the excellent location to Sag Harbor's Main Street and the Zagaya restaurant *upstairs. It was superb! The staff was very friendly and helpful. The rooms were small and the baths particularly small so just a heads up on that although the toiletries were really nice. The hotel has a great vibe at night with live music in the bar area on Thursday evenings. The weather was cool...absolutely gorgeous for early October so we didn't use the pool/cabanas (although it was heated). I did peek in the fitness room and it was very nice. Not enough time to check out the spa but there's always next time!"
SUSAN 4-night trip
Posted 2 days ago
Faraway Sag Harbor
Hyatt Place Long Island East End

Hyatt Place Long Island East End

10/10 Excellent
"Parking wasn’t convenient."
Carl 1-night trip
Posted 5 days ago
Hyatt Place Long Island 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.

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