TOP Hotels with Pool in Cutchogue, NY for 2026

Q: What are some accommodation options with pools in Cutchogue?

Pier Blue Inn Old Saybrook - Essex : Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton : Provides a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport : Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa : Hotel, 1-minute walk from The Hamptons Beaches. Offers daily, a seasonal outdoor pool and free self parking. Sag Harbor Inn : Features daily, a seasonal outdoor pool and sunloungers.

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 Pool

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Cutchogue hotels with a pool

Clinton Motel

Clinton

Dive into cool relaxation at this coastal motel's seasonal pool, where Hammonasset Beach State Park adventures await.

฿2,916 total

includes taxes & fees

2 Jun - 3 Jun

Individually decorated, individually furnished, desk, laptop workspace

Econo Lodge Inn & Suites Old Saybrook Westbrook

Old Saybrook

Soak in the serenity at this garden-view pool retreat offering refreshing summer escapes amid recently refreshed accommodation.

฿3,010 total

includes taxes & fees

7 Jun - 8 Jun

Seasonal outdoor pool, open 10:00 AM to 8:00 PM, pool umbrellas

Hamlet Inn

Southampton

Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.

฿9,793 total

includes taxes & fees

3 Jun - 4 Jun

North Fork Resort

Greenport

฿11,029 total

includes taxes & fees

15 Jun - 16 Jun

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Bentley Hotel Southampton

Southampton

Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.

฿16,335 total

includes taxes & fees

1 Jul - 2 Jul

The Penny Lane

Hampton Bays

Seasonal poolside relaxation awaits at this oceanfront hotel with sun loungers, umbrellas, and gardens.

฿9,258 total

includes taxes & fees

7 Jun - 8 Jun

The Hampton Maid

Hampton Bays

Splash into summer at this Hampton motel, where the seasonal pool and massage services await.

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.

฿11,010 total

includes taxes & fees

1 Jul - 2 Jul

View all properties

Choose what matters most at hotels with a pool in Cutchogue

Breakfast included

4 stars

Top Cutchogue Hotel Reviews

Sound View Greenport

10/10 Excellent

"Love being on the water"

The Atlantic Hotel

6/10 Okay

"Overall, I had a pleasant stay at this hotel. The room was comfortable, clean upon arrival, and the staff were friendly and helpful when contacted. The only issue I encountered was that I wasn't aware daily housekeeping was not included during my stay. As a result, I had to call the front desk to have my garbage removed and to request a fresh set of towels. Housekeeping came in the evening, but it would have been helpful if the housekeeping policy had been communicated more clearly at check-in or in the room information. Aside from that, my experience was positive."

Frequently asked questions

What are some accommodation options with pools in Cutchogue?

Pier Blue Inn Old Saybrook - Essex: Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Provides a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Hotel, 1-minute walk from The Hamptons Beaches. Offers daily, a seasonal outdoor pool and free self parking. Sag Harbor Inn: Features daily, a seasonal outdoor pool and sunloungers.

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, Pugliese Vineyards and Bedell Cellars 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.

Explore a world of travel with Expedia

More ways to book

Book Hotels with Pool in Cutchogue on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Cutchogue Hotels with Pool