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

Hotels with Swimming Pools in Cutchogue

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Cutchogue Hotels with Swimming Pools

This weekend
Next weekend

Our top choices for Cutchogue hotels with a pool

1. The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (607 reviews)
  • cleanliness
    Dive into the pristine oasis of the seasonal outdoor pool, complete with umbrellas and loungers for ultimate relaxation.
The price is S$210
includes taxes & fees
3 Nov - 4 Nov
The Bentley Hotel Southampton

2. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (762 reviews)
  • cleanliness
    Coastal bliss awaits at this private beach hotel with a seasonal pool and sunset views.
The price is S$272
includes taxes & fees
22 Nov - 23 Nov
Sound View Greenport

3. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (668 reviews)
  • cleanliness
    Dive into pool paradise at this oceanside retreat with sun loungers for ultimate relaxation.
The price is S$231
includes taxes & fees
16 Nov - 17 Nov
The Harbor Front Inn

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (297 reviews)
  • cleanliness
    Unwind in a beachfront haven with a refreshing seasonal pool, comfortable loungers, and breathtaking sunset views.
The price is S$389
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums

5. Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (517 reviews)
  • cleanliness
    Serene seasonal pool retreat with private beach access just 2 miles away offers the perfect summer escape on Long Island.
The price is S$177
includes taxes & fees
28 Oct - 29 Oct
Hamlet Inn

6. The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (1,000 reviews)
  • cleanliness
    Splash into summer at this modern hotel with tennis courts and a seasonal pool for sunny relaxation.
The price is S$188
includes taxes & fees
30 Oct - 31 Oct
The Atlantic Hotel

7. Ocean View Terrace Inn

Ocean View Terrace Inn
2.0 star property
Hampton Bays
8.8 out of 10, Excellent, (141 reviews)
  • cleanliness
    Beachside seasonal pool awaits with ocean adventures and relaxing massages nearby.
The price is S$248
includes taxes & fees
28 Oct - 29 Oct
Ocean View Terrace Inn

8. Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Take a dip in two refreshing pools at this Long Island hotel, where poolside relaxation meets marina adventure and family fun.
The price is S$190
includes taxes & fees
22 Nov - 23 Nov
Hyatt Place Long Island East End

9. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (681 reviews)
  • cleanliness
    Swim into serenity at this charming Sag Harbour retreat with a seasonal outdoor pool and balcony views.
The price is S$320
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn

10. The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.2 out of 10, Wonderful, (810 reviews)
  • cleanliness
    Splash into summer at this Hampton motel, where the seasonal pool and massage services await.
The price is S$309
includes taxes & fees
28 Oct - 29 Oct
The Hampton Maid
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Choose what matters most at hotels with a pool in Cutchogue

Top Cutchogue Hotel Reviews

Frequently asked questions

What are some accommodation options 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 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.

Explore a world of travel with Expedia