Top Cutchogue rentals with pool or private pool - New York

Explore Cutchogue rentals with pools

Premier Host

Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country

Sleeps 8 · 4 bedrooms · 1+ bathroom

North Fork, New Construction with heated pool, walking distance to beach

Sleeps 8 · 4 bedrooms · 2 bathrooms

Premier Host

Escape to serene 3-bedroom Cutchogue haven with pool, near beaches & vineyards.

Sleeps 6 · 3 bedrooms · 2 bathrooms

Relaxation Awaits-Fully renovated home heated pool, private manicured grounds.

Sleeps 6 · 3 bedrooms · 2 bathrooms

Top rated rentals with pools - Cutchogue

Premier Host

Beautiful home

From the day of booking, Andrew and Morgan were responsive and wonderful to communicate with. So generous with their time and had fantastic suggestions for restaurants and activities for our Thanksgiving week in their home. The house exceeded our expectations. Fully equipped with everything you need, beautifully furnished and so comfortable for the two families. Lots of space for the kids to play and entertain themselves, indoors and out. The view is breathtaking, we had to photograph it every morning and evening! We loved the beach - (only 5 minutes walk) wineries, restaurants, groceries and great coffee shops only a short drive (or bicycle ride) away. Thank you Andrew and Morgan for sharing your home with us. We made wonderful Thanksgiving memories and were full of gratitude! We will definitely be back.

Ashleigh B.

Stayed Nov 2021

View from the upper deck with Kayakers & Paddle Boarders enjoying the water

Beautiful rustic cottage in idyllic setting.

Very much enjoyed a relaxing stay in this delightful cottage which is nestled in a beautiful peaceful garden and artfully and comfortablely decorated. Perfect location - a minute walk to private beach and close proximity to all other local beaches and national park walks. Nancy was very helpful and communicative - and neighbor Rick was a perfect host. Perfect peaceful and relaxing getaway.

Jan W.

Stayed Oct 2018

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Frequently asked questions

Are there any holiday homes with a pool in Cutchogue?

Pick one of our 11 holiday homes with a pool and make a start on planning your trip to Cutchogue. Whether you want to be in Silver Beach, Montclair Colony, Greenport West or another much-visited neighbourhood, you'll discover the ideal poolside property on Stayz.

How much does it cost to stay in a holiday home with a pool in Cutchogue?

If you're hoping to save on your holiday home with a pool, Stayz's filters can help. After finishing your initial search, tailor your results based on your preferences, including star rating, price and features and amenities. We've got accommodation in Cutchogue for all sorts of budgets, so make the most of our filters to find your perfect stay.

When is the best time to book a holiday home with a pool in Cutchogue?

The best time to book a holiday home with a pool in Cutchogue is up to you! Start by checking the temperatures and weather conditions during different periods of the year. Also decide if you want to splash around in the high or the low season.

What holiday homes with a pool in Cutchogue have nice views?

Stay at a holiday home with a pool in Cutchogue and you can spend your days alternating between enjoying dips and staring out at terrific vistas. Some of our most popular home houses here offer coastal views.