17

Cutchogue, NY Houses for Rent with Pool

Section Image
  • /31

    $4,200 per month

    • 3 Beds
    • 3 Baths
    • 1,300 Sq Ft
    • House for Rent

    840 Little Neck Rd, Cutchogue, NY 11935

    840 Little Neck Road, Cutchogue - A lovely, ranch-style home, that offers a blend of comfort and charm that's hard to resist. The property boasts three bedrooms and three bathrooms. The main floor features 3 bedrooms, one being the primary bedroom complete with an ensuite. Cook up a storm in the large eat-in kitchen or serve meals in the separate dining area. The open and airy living

    Rita Rooney Douglas Elliman Real Estate

    840 Little Neck Rd, Cutchogue, NY 11935
  • /32

    $35,000 per month

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    535 Birch Ln, Cutchogue, NY 11935

    Newly built, completed in 2025! Spend your July in Cutchogue at this home located in a Sound-front community with private beach access. Private fenced backyard with heated in-ground pool and extra large patios. Coastal colors and up-to-the minute design will put you at ease for a month of relaxation. A huge screened porch overlooking the yard will be your favorite place to drink your morning

    Melissa Principi Douglas Elliman Real Estate

    535 Birch Ln, Cutchogue, NY 11935
  • /13

    $10,000 per month

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    2300 Pine Tree Rd, Cutchogue, NY 11935

    Welcome to 2300 Pine Tree Road, Cutchogue, where every day feels like a vacation. The property boasts a fully fenced, heated saltwater pool, a perfect spot for relaxing. Multiple outdoor dining areas provide ample space for entertaining or enjoying a quiet meal under the stars. For sports enthusiasts, the property features a basketball and pickleball court, offering endless hours of fun.

    Rita Rooney Douglas Elliman Real Estate

    2300 Pine Tree Rd, Cutchogue, NY 11935
  • /25

    $30,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    250 Pine Tree Ct, Cutchogue, NY 11935

    Escape to your private Cutchogue oasis this summer! This stunning home boasts four bedrooms, including two en-suite, and 3.5 baths, offering luxurious accommodations for your getaway. Unwind in the in-ground pool or lounge on the wrap-around porch overlooking a tranquil creek. Two living rooms and an open-concept kitchen provide ample space for entertaining, while the wooded lot ensures

    Mackenzie Needham Daniel Gale Sothebys Intl Rlty

    250 Pine Tree Ct, Cutchogue, NY 11935
  • /26

    $140,000 per month

    • 4 Beds
    • 4.5 Baths
    • 2,000 Sq Ft
    • House for Rent

    4705 Nassau Point Rd, Cutchogue, NY 11935

    SPARKLING BAY FRONTBay front living in prestigious Nassau Point. This spacious, newly renovated home features 4+ bedrooms, large living room with fireplace, eat-in kitchen and an office. 100 feet on the Bay and a full acre, waterside deck overlooking Peconic Bay, steps to private beach, gunite & heated pool, pool house with a kitchenette, recreation area, changing area with a full bath, half

    Sheri Winter Parker Corcoran

    4705 Nassau Point Rd, Cutchogue, NY 11935
  • /25

    $30,000 per month

    • 5 Beds
    • 5 Baths
    • 3,500 Sq Ft
    • House for Rent

    5270 Nassau Point Rd, Cutchogue, NY 11935

    Have the best North Fork summer ever in this newly renovated home in prestigious Nassau Point! At its heart is a sunny great room with a soaring cathedral ceiling. The chef’s kitchen includes premium appliances, a large island, and flows into the living room with backyard views. The formal dining room, with bay views, is perfect for more formal gatherings.The main floor features a queen

    Diane Arpaia Signature Premier Properties

    5270 Nassau Point Rd, Cutchogue, NY 11935
  • /25

    $35,000 per month

    • 6 Beds
    • 7.5 Baths
    • 7,000 Sq Ft
    • House for Rent

    15105 Oregon Rd, Cutchogue, NY 11935

    Don't miss your chance to rent this unparalleled estate, nestled on 5 picturesque acres among the region's most prestigious vineyards.This magnificent home is a perfect blend of elegance and tranquility, ideal for those seeking a refined living experience.Spanning an impressive 7,000 sf, the residence is designed with sharp attention to detail. Floor-to-ceiling windows flood the space with

    Lisa Gillooly Compass Greater NY LLC

    15105 Oregon Rd, Cutchogue, NY 11935
  • /13

    $9,500 per month

    • 4 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    3475 Wunneweta Rd, Cutchogue, NY 11935

    Welcome to your serene off-season retreat in -a stunning rental that epitomizes modern elegance and tranquil seclusion. This exceptional residence offers 4 spacious bedrooms and 3 luxurious bathrooms, all nestled on an expansive 43,560 square foot lot. Step inside to discover a beautifully designed interior featuring a chef's kitchen, perfect for culinary enthusiasts. The open-concept living

    Jennifer Benton Compass Greater NY LLC

    3475 Wunneweta Rd, Cutchogue, NY 11935
  • /26

    $24,200 per month

    • 4 Beds
    • 4 Baths
    • 2,400 Sq Ft
    • House for Rent

    1100 Alvahs Ln, Cutchogue, NY 11935

    Come and enjoy the privacy that lies behind the doors of this reimagined modern ranch. Once inside you will be thrilled by the level of detail in this 2023 gut renovation. As you enter the home, you are welcomed with expansive views across the large backyard onto the surrounding vineyards. The 14' lofty ceiling highlights the kitchen and dining space creating a bright and airy feel for you to

    Sheri Winter Parker Corcoran

    1100 Alvahs Ln, Cutchogue, NY 11935
  • /27

    $4,000 per month

    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft
    • House for Rent

    795 Monsell Ln, Cutchogue, NY 11935

    Your Summer Waterfront Retreat Is Now Available And Waiting For You! Gourmet Chef's Kitchen With Stainless Steel Appliances. Gas Stove. Open Plan Living, Filled With Natural Light. Built In Closets In All 3 Bedrooms. Studio/Extra Bedroom On Ground-floor. Wood Burning Stove. Recent Upgrades Include The Following: New Anderson Windows Throughout In 2021. New Pool Liner And Travertine Pavers

    Pete Halpin Douglas Elliman Real Estate

    795 Monsell Ln, Cutchogue, NY 11935
  • /15

    $15,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,800 Sq Ft
    • House for Rent

    530 Stillwater Ave, Cutchogue, NY 11935

    Perfect summer getaway! 3 bedrooms, 2.5 bathrooms, in-ground pool, close to beach, business district, vineyards and restaurants. Two week minimum stay., Additional information: Appearance:very good

    Erin Kaelin Signature Premier Properties

    530 Stillwater Ave, Cutchogue, NY 11935
  • /26

    $40,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,250 Sq Ft
    • House for Rent

    2430 Dignans Rd, Cutchogue, NY 11935

    Cutchogue North Fork: Spend August-LD 2026 in this beautifully appointed & very private Long Island Sound front home at 2430 Dignans Road, Cutchogue: come find out why the owners call it North Cliff. Spectacular decks & pool set high on the cliffs overlooking the LI Sound - private easy steps to beach. On the other side forever views of Oregon Road farmland. Published in international Fashion

    Nicholas Planamento William Raveis New York LLC

    2430 Dignans Rd, Cutchogue, NY 11935
  • /20

    $22,000 per month

    • 4 Beds
    • 2 Baths
    • 2,600 Sq Ft
    • House for Rent

    25 Moose Trail, Cutchogue, NY 11935

    Discover the perfect blend of comfort and luxury in this stunning 4-bedroom Cape, ideally situated in the heart of Cutchogue. Designed for both relaxation and entertainment, this home features a chef’s kitchen and an array of spacious living areas, including a formal dining room, game room with a pool table and arcade games, plus a first-floor bedroom and full bath—all tastefully

    Jeanmarie Bay William Raveis New York LLC

    25 Moose Trail, Cutchogue, NY 11935
  • /30

    $30,000 per month

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft
    • House for Rent

    3655 Pequash Ave, Cutchogue, NY 11935

    New to Market FLEET's NECK Rental! Walk to Beach from your Private FABULOUS SUMMER OASIS. 4 Bedroom and 2 Full Bath Contemporary Home on tucked away Lot Set Well-Back from Road on 1 + acres. Offers Sleek Main Floor Living Area with Fireplace, Chandeliered Dining Area, Foyer, Light Bright Kitchen with All Stainless-Steel Appliances, that leads to a Furnished 2-Level Deck with Both Living and

    Deirdre Fedun Fedun Real Estate Inc

    3655 Pequash Ave, Cutchogue, NY 11935
  • /23

    $22,500 per month

    • 4 Beds
    • 4 Baths
    • House for Rent

    935 Southern Cross Rd, Cutchogue, NY 11935

    Available 2025: April: $12,000, May: $17,500, June: $22,500, July: $35,000. Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large gatherings. The first

    Mariah Mills Daniel Gale Sothebys Intl Rlty

    935 Southern Cross Rd, Cutchogue, NY 11935
  • /29

    $10,000 per month

    • 3 Beds
    • 2 Baths
    • 1,474 Sq Ft
    • House for Rent

    2600 Oregon Rd, Mattituck, NY 11952

    MAGIC ON OREGON ROAD Romance, elegance, and the bucolic backdrop of Oregon Road make this home a standout! Nestled within a vineyard, this 3 bedroom, 2 bath vintage farmhouse charmer lies on 2 acres with an in-ground pool and endless vineyard views. Short distance to tasting rooms, farm stands, renowned restaurants, vineyards, and fantastic beaches that the North Fork is known for! $10,000.00 for

    Sheri Winter Parker Corcoran

    2600 Oregon Rd, Mattituck, NY 11952
  • /35

    $24,000 per month

    • 3 Beds
    • 2 Baths
    • 1,800 Sq Ft
    • House for Rent

    Unlisted Address

    Mattituck, North Fork: Sunshine and solace await you in this immaculate and recently renovated vacation home with a brand NEW, heated, saltwater pool (16x34 gunite)! Large open and bright rooms with lots of natural light allow you to relax in comfort and enjoy your time off. Home accommodates a maximum of 6 guests and features first floor bedroom with luxurious bath, open concept dining

    Nicholas Planamento William Raveis New York LLC

    Unlisted Address
How to Rent a Home