Home Vacation Rentals By Owner In Cutchogue, NY

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Exceptional(2)

$296.57

/ Nightly
Private Vacation Home

Walk to Beach: Long Island Wine Country Home!

Cutchogue, New York, United States

Wood-Burning Fireplace | Sunroom Dining Area | Surrounded by WineriesbrbrExperience Long Island's vibrant North Fork wine country like a local when you stay at this charming 'Vintage Cottage.' Nestled in the sought-after beach community of Nassau Point in the heart of wine country, this 3-bedroom, 1.5-bath vacation rental is the perfect place for your Cutchogue getaway. After a day of exploring, return home to cozy up by the fireplace or enjoy an evening stroll to the beach.brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bed br- Bedroom 2 (Peach Room): 1 full bed br- Bedroom 3 (Pink Room): 2 twin beds br- Basement Game Room: 1 sleeper sofa, 1 twin bunk bedbr- Additional Sleeping: 1 portable cribbrbrOUTDOOR LIVINGbr- Private backyard, hammockbr- Wood-burning fire pit w/ seatingbr- Patio, gas grillbr- Swingset, kid's tablebr- Beach towels, outdoor showerbrbrINDOOR LIVINGbr- Wood-burning fireplace, Smart TVbr- Sunroom, dining tablebr- 4-person dining nookbr- Dedicated office, 2 monitorsbr- Basement entertainment roombr- Board games, booksbr- Washer & dryer, laundry detergent brbrKITCHENbr- Electric stove, oven, dishwasher, microwavebr- Drip coffee maker, toaster, Crockpotbr- Cooking basics, spices, knife setbr- High chair, dishes & flatwarebrbrGENERALbr- Free WiFibr- Central heating & A/C, ceiling fansbr- Linens, towels, iron/boardbr- Complimentary toiletries, hair dryerbrbrACCESSIBILITYbr- 3 stairs requiredbr- Single-story home w/ basementbrbrPARKINGbr- Driveway (2 vehicles)brbr-- THE LOCATION --brbr- Centrally located in Long Island wine country; surrounded by vineyards & walking distance to the beachbr- 0.5 miles to Fisherman Beachbr- 3-5 miles to Lenz Winery, Pugliese Vineyards, Duck Walk Vineyards, Pellegrini Vineyards, & Mcall Winesbr- 4 miles to Cedars Golf Clubbr- 18 miles to Long Island Aquarium & Cranberry Bogbr- 46 miles to Long Island MacArthur Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This home requires 3 stairs to access, as well as an additional staircase to the basement entertainment room
Bed 5

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Bath 2

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Sleep 7

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Exceptional(3)

$1240.71

/ Nightly
Private Vacation Home

Wine Country Oasis in the Heart of Nassau Point

Cutchogue, New York, United States

Come spend a relaxing vacation in this beautiful home featuring a gourmet chef's kitchen with Viking and Sub-Zero appliances. The great room has cathedral ceilings overlooking the pool and gardens. Multi-level backyard with various seating areas, gorgeous landscaping, pool house with cabana and 2 outdoor dining areas. Finished basement has a playroom filled with toys/games and an adult game room complete with darts, foosball and arcade games. Enjoy private beach access within walking distance and public beach access is less than 5 minutes away.brbr5 bedroom. 3 Full Bath. 2 powder rooms. Primary suite, with gorgeous views, complete with spa bathroom home office and gym. Spacious Junior Master bedroom with ensuite. Kids Bedroom with 2 trundle beds and a crib. The main floor has a guest bedroom which opens right out to the deck and a Library with a murphy bed/combo desk that epitomizes relaxed luxury. Get cozy in the great room by the fireplace on a crisp fall night or sit out on the pool deck level to soak up the sun. Enjoy a soak in the hot tub or take in the stunning views from every front facing window. Other amenities include a mudroom with pantry and o1/2 bathroom, spacious entryway and picturesque coastal style dining room with epic views of the crystal clear water. brbrWe do not rent to bachelor/or bachelorette parties. 2 week minimum
Bed 5

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Bath 6

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Sleep 16

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Exceptional(3)

$765.91

/ Nightly
Private Vacation Home

Tranquil 5 Br North Fork Retreat With Pool And Huge Yard, Walk To Beach

Cutchogue, New York, United States

Our beautiful home in Cutchogue, on Long Island's North Fork, is located on a very quiet, woodsy street. The house has five bedrooms and two and a half baths, and is perfect for two families or an extended clan. Upstairs are the master bedroom with king-sized bed; kids' room with two twins and a trundle; and third bedroom with queen-sized bed. Full and half-baths upstairs, as well as a fully stocked kitchen (stove, dishwasher, fridge, microwave, toaster oven, and full set of spices, condiments, and indoor/outdoor service), living room, formal dining room, and family room with TV, cable, Netflix, Apple TV, game cart, and more.brbrDownstairs is a bedroom with two twins and a toddler bed (convertible back to crib); and a very large bedroom with a queen-sized bed and plenty of room for a pack-and-play. There is a also a full bath downstairs, and an enormous playroom stocked with books, games, a ping-pong table, dollhouse, art supplies, and more.brbrOutside is a full acre of flat, grassy lawn and a private, fully fenced pool with shaded table and chairs, lounges, pool toys, etc; and a 'summer house' -- a small, round room with electricity and screened windows, with table that seats 10 for meals.brbrThe local beach, with playground, lifeguards, restrooms, and picnic tables, is a short walk away (10-15 minutes depending on how slow you walk/your stroller rolls). Our private community beach is just 1/10th of a mile further along.brbrIt's a wonderful place for fishing, walking, shell fishing, swimming, and all-around relaxing, breathing, and connecting. brbrPreference is for two-week minimum stays, but full weeks-10 days considered. The house is a two-hour drive from most New York City locations; walking distance (just under a mile) from the Hampton Jitney stop in Cutchogue, and a short drive to the LIRR stations in Mattituck or Southold. Surrounded by vineyards, farms, and beaches. There is a pack-n-play at the house, as well as a safety gate, booster seats, and about a million beach toys.
Bed 5

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Bath 3

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Sleep 10

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$270.0

/ Nightly
Private Vacation Home

North Fork Farms & Vineyards Near Beaches & 40 Minutes From The Hamptons

Cutchogue, New York, United States

*Available as a Year Round Rental at $5,000 per month. Minimum 14 Night Stay(Town of Southold Requirements). Artist/Designer's Light Drenched Just Renovated Mid Century Ranch located on the gateway to Oregon Road's open farmland and multiple vineyards flanked by the Long Island Sound. This 3 Bedroom, 2 Full bath Ranch(MB walk in shower with 2nd vanity & 2nd bathroom tub with double sinks) offers amazing views from front porch, 2 decks and multiple outdoor dining areas in an ideal relaxing North Fork escape in the sunniest spot in New York state(Cutchogue). While just 1800 sq ft; this centrally air conditioned mid century just renovated ranch feels spacious and light drenched. With sweeping vistas of protected organic farm lands flocked with cows and calves from the front porch and a large expansive backyard bordered by a tree farm you will feel miles away from it all. The vibe is bright, stylish and contemporary mid century with a vaulted ceiling Open Floor Plan great room layout. Designed for easy living & entertaining in mind; the chefs(s) in the house enjoy prepping meals amongst friends and family at the expansive island stocked with all the right tools including a wine fridg and pot filler for your farmstand corn on the cob and lobster dinners. This eat in kitchen with dining table and island seating (offers dining for 8 comfortably) leads to a glass door to the backyard deck. The Master bedroom en suite is spacious with a seating area and a wall of glass doors to a private deck flanks one side of the living Room area with flat screen television with 2 additional bedrooms flanking the other side. The second Bedroom offers two 2 Twin Beds and a Desk. The third bedroom is a Guest Room that doubles as a Den/Office with two flat screen television and a built in digital friendly workstations. While the basement is rustic and unfinished; it is a great rec room escape for the young and young at heart. An arts and craft table and wii set up and play area for children make this a great asset for a rainy day and children under feet. brbrEnjoy relaxing moments with coffee or drinks on the front porch overlooking the farm or dining on the deck. Just a short drive to Local Fish and Grocery Shopping, and Cutchogue Village where you will find some great dining in charming settings. Centrally located between Love Lane in Mattituck and Greenport Village, and located in the heart of wineries where you can explore the best of the North Fork's many Tasting Rooms and endless Harvest festivals. Enjoy sunsets and meals in the park like expensive backyard with over 27 fruit trees on 2 acres that is bordered by a tree farm. Ideal location for runners, biking and exercise enthusiasts, nature enthusiasts and or for strollers in the mood for a glass of wine at Lieb Vineyard's or Shinn Vineyard's tasting rooms. Just 5 minutes to multiple Town of Southold Tennis & Pickle Ball Courts and playgrounds. Short car drives to the beaches or bike to the Long Island Sound. brAdults and children will love the expansive backyard with 27 fruit bearing trees on the property. brbrThe backyard is furnished for grilling, dining and relaxing. There are a couple of adult bikes and a couple of children's size bikes for riding and touring the area which borders one of the nicest farm roads on the North Fork.Child friendly for easy living and spending great quality time together and traveling light.brbrJust two hours from Manhattan, forty minutes from the Hamptons and a short ferry ride to Shelter Island, the North Fork is considered to be a beautiful old world jewel surrounded by water and flocked with nearly fifty vineyards and tasting rooms to explore. The North Fork is often referred to the Non-Hamptons of the North and South Forks of the East End of Long Island. Casual and relaxing, its' vibe and focus on landscape, preservation, farm to table food, nature, vineyards and the calm waters of the Long Island Sound and Peconic Bay the experience is low key in comparison to its' opposite fork of the Hamptons.brbrWine and Beach Country - Cutchogue is located in brthe Heart of Wine Country on the North Fork of Long Island, a 40 minute drive to the Hamptons, or two short enjoyable ferry rides to Sag Harbor(a quaint whaling village in the Hamptons). brbrManhattan is just a couple of hours away. The Hampton Jitney bus(just 5 minutes away) and the Long Island Railroad(10 minutes away) are convenient ways to get to NYC. brbrCutchogue is a bucolic town in the heart of the North Fork a contender for the Hamptons. Surrounded by nearly 50 vineyards, open farm lands, the Long Island Sound and the Peconic Bay Cutchogue is a hamlet of the North Fork. Foodies enjoy farm to table foods available in farm stands for cooking at home as well as in local restaurants throughout. Turn back the hands of time to a simpler time with local shopping, golf, horse back riding, tennis, museums and bay and Long Island Sound and Peconic Bay beaches. This area is truly special attracting international devotees, weekenders from Brooklyn and Manhattan and residents of Metropolitan New York suburbs. brbrSettled in the 1600's Cutchogue is a small quaint historical village nestled in between the coastal villages of busier North Fork towns of Greenport and Mattituck. The villages offer dining, museums, activities, boating, beaches and shopping. For children, Greenport offers boat rides, a Carousel and park. Perfect spot to explore the 'North Fork', vineyards, beaches, coastal towns, farms, and now an area full of vineyards that are now rivaling Napa Valley in California. Just five minutes away lies the Hampton Jitney Bus to Manhattan and 10 minutes away is the Long Island Railroad. The North Fork is rural and you will want to explore all villages and the many beaches so you will need a 'Car' to get around.brbrIdeal for Couples, and Family. Everything you need is on the first floor. Washer and Dryer in the basement. brFor Families...Bring your helmets and enjoy using our Toddler, Child and 3 Adult Bikes...For children...High Chair, Books, Board Games
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Bath 2

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Sleep 6

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$287.4

/ Nightly
Private Vacation Home

Charming home with a fire pit, grill, W/D, & AC - North Fork Wine Country

Cutchogue, New York, United States

The Endless Summer CottagebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis charming coastal retreat is everything you've dreamed of! Centrally located in North Fork Wine Country, you will have easy access to a plethora of wineries, beaches, boating spots, and fishing docks. Set sail at the Old Cove Yacht Club, practice your swing at Cedars Golf Course, and indulge in some magnificent stargazing every Saturday at the Custer Institute. brbrThe moment you pull up to this quintessentially coastal cottage, you will feel right at home. Head inside and take note of the spacious living room's warm wood flooring, soft seating, and large TV. The adjacent well-appointed kitchen presents a light-filled place to play chef. Dining as a family comes naturally at the dining table, or alfresco on the back patio. brbrThe bedrooms are equally sizable and comfortable with soft linens and little homey touches of comfort. Whereas the tiled bathrooms ooze old-school charm. Additionally inside, appreciate having access to a private washer/dryer, and central air-conditioning. brbrOutside, enjoy the warm breeze from the home's backyard where a grill and seating are surrounded by lush landscaping and the warm glow of twinkle lights. brbrTHINGS TO KNOWbrStreaming services available with guests’ own account(s).brFireplace is not for guest use.brRenters have beach rights and free parking at the Nassau Point Causeway Beach, which is 5 minutes away by car!brbrParking notes: There is free parking available for 2 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.
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Bath 2

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Sleep 6

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$444.06

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Private Vacation Home

Family-friendly getaway walk to beach in private community, w/ park, playground

Cutchogue, New York, United States

Sunny, open floor plan retreat, lots of privacy on 1 acre of land — perfect for families!brWelcome to the NOFO—where you'll be greeted by beautiful beaches, dozens of wineries and some of the best cuisine New York has to offer. Our private community feels like paradise - with 2 beaches, a waterfront park and playground, and a marina you can walk to in just a few minutes. The community is on a peninsula so you are always surrounded by water. It's truly idyllic. brbrAnd welcome to our home: a homey, cozy retreat located in Cutchogue—walking distance to town, Braun's Seafood, King Kullen, Black Sheep Bagels, Cutchogue Library, a diner, deli, pizza place, liquor store, winery, and more (yes, all walkable within 15-20 min!). Not to mention the plethora of activities, restaurants, wineries, and gatherings happening all across the North Fork. brbrUpon entering our house, you'll be greeted by vaulted ceilings in the entrance/living room. With an open concept, walk back and forth from the kitchen to the living room with ease. The long hallway offers privacy and separation between the bedrooms and the rest of the house. This property offers the perfect space for families looking to entertain, dine, grill and enjoy the peacefulness of our house on a large, private 1 acre property, and private community.brbrThe house has been curated with love and we hope you enjoy it as much as we do!brbrAmenities include, but are not limited to:brbr- 3 bedrooms (1 king, 1 queen, 1 crib + 1 queen blow up mattress)brbr- 2 full bathroomsbrbr- Google Nest Thermostatbrbr- washer & dryerbrbr- Wifi includedbrbr- Beach chairs, umbrellas, toys, beach towels, bath towels, linens, kids toys, fully stocked kitchen all includedbrbr- Deck with furniturebrbr- Kids toysbrbr- Air conditioning and heatbrbr- queen blow-up mattressbrbr- No smoking permittedbrbr- located in private community, private beachbrbr- Town beach parking permits available for stays of 30 days or longer
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Bath 2

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Sleep 6

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$826.77

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Private Vacation Home

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

Cutchogue, New York, United States

Escape to the heart of the North Fork and experience the ultimate retreat at our charming vacation rental, located in Cutchogue, NY. Perfect for families, couples, or a group of friends, this beautifully maintained home offers the ideal blend of comfort, convenience, and scenic beauty.brbrProperty Highlights:brbr3 Bedrooms, 2 Bathrooms – Sleeps up to 6 guests comfortably.brSpacious Living Area – Bright and airy with cozy seating, flat-screen TV, and rustic décor.brCozy family room featuring a warm wood fireplace and comfortable sectional couches, perfect for relaxing and spending time together. Fully Equipped Kitchen – Stainless steel appliances, ample counter space, and all the essentials for home-cooked meals.brOutdoor Oasis – Large deck with outdoor seating, BBQ grill, lush backyard, and an inground pool for relaxation and fun.brWater Access & Views – Just steps from the bay, perfect for kayaking, paddleboarding, or simply soaking in the serene views.brClose to Wineries & Attractions – Minutes from renowned North Fork wineries, farm stands, beaches, and charming local shops.brWhy You'll Love It: Whether you’re here to unwind by the water, explore the vibrant wine country, or indulge in farm-to-table dining, this home is your perfect getaway. With its prime location and inviting ambiance, your North Fork vacation will be unforgettable! The pool is 16 x 32 feet. 6 feet deep in the deep end. The house has central air conditioning throughout.
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Bath 2

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Sleep 6

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