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 a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport : Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Atlantic Hotel : Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton : Offers a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa : Hotel located near Splish Splash Water Park. Offers a snack bar/deli, a seasonal outdoor pool and complimentary high-speed (wired) Internet access.

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

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

This weekend

Next weekend

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.

Rp1.834.317 total

includes taxes & fees

30 Jun - 1 Jul

The Penny Lane

Hampton Bays

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

Rp5.463.011 total

includes taxes & fees

14 Jul - 15 Jul

North Fork Resort

Greenport

Rp7.610.886 total

includes taxes & fees

5 Jul - 6 Jul

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.

Rp1.659.748 total

includes taxes & fees

19 Jul - 20 Jul

The Inn And Spa At East Wind

Calverton

Float in year-round comfort at this Long Island hotel's pristine indoor pool retreat.

Rp4.035.797 total

includes taxes & fees

27 Jul - 28 Jul

Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool loungers

Hampton's Vacation Inn

Hampton Bays

Soak in poolside bliss at this Hampton guesthouse with refreshing seasonal pool, tennis court, and nearby beach activities.

Rp3.690.157 total

includes taxes & fees

29 Jun - 30 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.

Rp5.295.234 total

includes taxes & fees

12 Jul - 13 Jul

Indoor pool, 2 outdoor pools, open 5:00 AM to 10:00 PM, pool umbrellas

Saybrook Point Resort & Marina

Old Saybrook Center

Swim into serenity with three breathtaking pools and luxurious loungers for perfect poolside days at this resort.

Rp7.443.653 total

includes taxes & fees

30 Jun - 1 Jul

View all properties

Choose what matters most at hotels with a pool in Cutchogue

Breakfast included

4 stars

Top Cutchogue Hotel Reviews

The Hampton Maid

10/10 Excellent

"Our stay at the Hampton maid was absolute perfection from start to finish. The representative at the front desk, went above and beyond to make us feel welcome, ensuring a seamless check-in and offering incredible personalized recommendations for the area. When we opened the door to our room, we could not believe the features that were offered to us for our stay. Refrigerator was filled with cold beverages for purchase also snacks, and other amenities located on the table near the window. The bathroom products they offered were top notch with incredible fragrances. The linens were crisp and clean, and the comforter was amazing. The pool was clean and inviting while the lounge chairs were comfortable, and they also offered pool towels that were extremely large and thirsty. Our first night we dined in the hotel restaurant and took advantage of the happy hour menu, which was extensive and reasonably priced . The presentation of each item that we ordered was flavorful and delicious. The bartender had extensive knowledge of the wine list and suggestions were also offered by the head chef. Upon the completion of our dinner we return to our room and sat outside on our deck. It felt like we were sitting in a mountain like setting as we enjoyed the serenity of the surroundings. We could not have picked a better spot and amore enjoyable two night retreat. This place is worth every penny"

The Pridwin Hotel

8/10 Good

"We were at the Pridwin because of a family wedding on Shelter Island. What an absolutely beautiful hotel! The location is fabulous, right across from the bay and the hotel is designed to really take advantage of the views. Our compliments and thanks to the outstanding staff, they were so warm and helpful! I would go back again in a heartbeat."

Frequently asked questions

What are some accommodation options with pools in Cutchogue?

Pier Blue Inn Old Saybrook - Essex: Offers a private beach, a seasonal outdoor pool and 2 bars. Sound View Greenport: Hotel located near The Hamptons Beaches. Provides 2 outdoor tennis courts, a seasonal outdoor pool and free self parking. The Atlantic Hotel: Hotel located near The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and complimentary wireless Internet access. The Bentley Hotel Southampton: Offers a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa: Hotel located near Splish Splash Water Park. Offers a snack bar/deli, a seasonal outdoor pool and complimentary high-speed (wired) Internet access.

What is there to see and do in Cutchogue?

Explore places such as The Hamptons Beaches while you're in the area. Make a point to visit attractions such as 8 Hands Farm.

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