
Vacation rentals with a pool in Cutchogue
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cutchogue
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Serene, private, Hamptons oasis; 1 block to dining
Experience the calm and stillness of this serene home. Enjoy the privacy of your own space. Designed to be a zen oasis for you! Relax poolside with nature surrounding you; you may spot a deer or bunny on the property! Spark up the BBQ + firepit under the starry sky; sip your morning coffee on the porch, enjoy 80' streaming TV. You will be in an ideal location; you can walk just 1 block to waterfront cafe + dining w/ the best sunsets. Drive 3-10 minutes to Main Street, beaches + so much more!

Brand new house with an all year round hot tub.
Your family will be close to everything when you stay at this centrally-located place. Very close beaches near dune road. Movie theaters, supermarkets, liquor store, farms and a bunch of local restaurants that you can visit.DJs are not allowed. Loud music and parties are strictly prohibited. It's a very quiet, relaxing, and peaceful neighborhood. No smoking inside the house.check in 3pm check out 11am extra charge. If you don't check out 11am.a minimum of 5 cars, no more than 5 cars

PRIVATE BASEMENT APARTMENT WITH POOL IN SAG HARBOR
Beautiful basement apartment partially in-ground, with many windows and private entrance is located in Sag Harbor , 3 minutes from village and Heavens Bech by car or 15 minutes walking distance . The apartment has king size bed and comfortable sofa in the living room . In the kitchen you can find coffe maker , toaster , microwave, dishwasher, small fridge , hot plate for light cooking . Tv , WiFi , Airconditoining , access to pool from May till end of the September .

North Fork Farmhouse with Saltwater Pool
Enjoy spectacular sunsets from the great room and deck overviewing your secluded hedged yard and saltwater pool. Located in the heart of the North Fork this 1820s farmhouse with modern amenities is nestled amongst vineyards and farmland with dramatic views in every direction. Quaint villages, premier restaurants, wineries, farms and beaches surround you. A truly magical, peaceful paradise for you and your group. Note pool is open May through mid October.

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach
Unwind in Hamptons Bliss! A coastal oasis awaits at this exquisite vacation house. Immerse yourself in luxury, from the elegant interiors to the serene outdoor retreat including a massive fenced-in salt water heated pool (Memorial Day to Labor Day) that will leave you in awe. Indulge in beachside bliss, upscale shopping, and culinary delights. Create memories that will linger long after the sun sets over the horizon. Your dream Hamptons getaway starts here!

Beautiful Waterview Condo on the North Fork of LI
Waterview luxury suite accommodates up to 6 guests with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. This location is minutes from town as well as wineries and centrally located to the ferry which can take you to Shelter Island and the South Fork. The resort is well maintained with a pool , BBQ grills and private beach access as well as ample parking for guests.

Private Oasis W/Stunning Vinyard and Pool Views
Enjoy spectacular wine country sunset views from the living room that extend to the gorgeous saltwater gunite pool and spa. (Please note THE POOL AND SPA (attached hot tub) are OPEN FROM MAY 1 - OCTOBER 15 only). Beautifully decorated, comfortable home with an updated chef's kitchen and fireplace. Fabulous restaurants, wineries, farms, beaches and exquisite small towns all nearby. Simply put, a magical, peaceful paradise for you and your group.

Luxury Hamptons Home with Heated Saltwater Pool
Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

Private Cozy Cottage with Pool / Private Beach
**POOL CLOSES SEPTEMBER 30TH** **POOL opens last week of May** This is a guest house for 1 or 2 adults. Its separate from the main house. Kids are allowed but must bring own sleeping arrangements. You do NOT have to do any chores before checking out. **PETS NOT ALLOWED** I hate to do this but someone ruined it for everyone. Max Occupancy: 4 Guests can only bring 1 vehicle since there is not enough room in the driveway

Waterfront Escape | Private Beach, Pool & Views
Overlooking the Long Island Sound, this beautiful waterfront condo is the perfect North Fork coastal escape. Enjoy peaceful mornings with panoramic water views, spend your days soaking up the sun on the private beach, and unwind on the waterfront deck as the sun sets over the Sound. Located just minutes from Greenport Village, you’ll be close to charming boutiques, local farms, award-winning wineries, and gourmet dining.

Astounding Watermill 5 Bedroom home with Pool
Situated off of a quiet lane on a half-acre of land, updated, modern residence offers a peaceful and quiet Hamptons getaway. 5 bedrooms / 3 modern bathrooms offers a relaxing escape. Large open kitchen leads out to the back garden, pool and indoor-outdoor eating areas. Please read the additional disclosures, guidelines, and rules. No events, no parties, no smoking –

Secluded Farmhouse - Studio Apartment Style Unit
Private studio suite with separate entrance and full bath in a modern North Fork farmhouse on a peaceful farm property. Enjoy a screened porch, fire pit, and outdoor seating. Includes mini fridge, Keurig, tea, homemade granola, and seasonal eggs/produce. Attached to our home, so some light household noise is possible. Private chef + yoga services available.
Popular amenities for Cutchogue rentals with a pool
House rentals with a pool

Private & Pristine with Pool and Kid’s Playard

4 Bedroom Sag Harbor Home w/ Pool & Tennis Access

Newly Renovated 3Bed/2 Bath - Hamptons Getaway!

Luxury Hamptons Poolside Paradise w/ Outdoor Sauna

East Hampton Oasis - Pool and Hot Tub

North Fork Sound Front Home with Pool

Beach House Feel - Newly renovated Backyard Oasis

Secluded Luxury: New Gunite Pool, Walk to Bay
Condo rentals with a pool

One Bedroom Apartment Nestled in the Dunes

Greenport Getaway at Cliffside Condos

Water front, sunsets, sail boats, min stay 30 days

Beautiful condo on Long Islands Northfork

Cliffside Resort Poolside Condo A106

Waterfront Elevated Bungalow - Spectacular Views

Newly Renovated Modern Townhouse w/Pool & Tennis

1856 Trading House close to water
Home rentals with a private pool
East Hampton Villa | Heated Saltwater Pool & Beach

Explore the Water & Woods at a Relaxing Retreat
Enchanting Home with Large Decks and Heated Pool
Perfect Getaway at Sunny Modern Shampton LakeHouse
Saltbox with Separate Poolhouse in Northwest Woods
When is the best time to visit Cutchogue?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$79,071 GYD | G$80,953 GYD | G$92,249 GYD | G$132,412 GYD | G$146,218 GYD | G$143,917 GYD | G$184,080 GYD | G$183,034 GYD | G$146,218 GYD | G$104,591 GYD | G$112,122 GYD | G$99,361 GYD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about vacation rentals with a pool in Cutchogue

Total vacation rentals
Explore 30 vacation rentals in Cutchogue

Nightly prices starting at
Cutchogue vacation rentals start at G$52,296 GYD per night before taxes and fees

Verified guest reviews
Over 1,170 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Cutchogue vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Cutchogue rentals

4.9 Average rating
Cutchogue stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Beachfront rentals Cutchogue
- House rentals Cutchogue
- Pet-friendly rentals Cutchogue
- Rentals with a fire pit Cutchogue
- Rentals with a washer and dryer Cutchogue
- Family-friendly rentals Cutchogue
- Rentals with a kayak Cutchogue
- Waterfront rentals Cutchogue
- Rentals with a hot tub Cutchogue
- Rentals with beach access Cutchogue
- Rentals with a fireplace Cutchogue
- Rentals with outdoor seating Cutchogue
- Rentals with a patio Cutchogue
- Fitness-friendly rentals Cutchogue
- Rentals with pools Suffolk County
- Rentals with pools New York
- Rentals with pools United States
- Yale University
- Cooper's Beach, Southampton
- Fairfield Beach
- Charlestown Beach
- Mohegan Sun
- Ocean Beach Park
- Robert Moses State Park Beach
- Foxwoods Resort Casino
- Mystic Seaport Museum
- Sunken Meadow State Park
- Hammonasset Beach State Park
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Blue Shutters Beach
- Sherwood Island State Park
- Compo Beach
- Amagansett Beach
- Orient Beach State Park
- Wölffer Estate Vineyard
- Mount Southington Ski Area
- Ocean Beach
- Meschutt Beach





