
House vacation rentals in Cutchogue
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Quick stats about house rentals in Cutchogue

Total vacation rentals
Explore 80 vacation rentals in Cutchogue

Nightly prices starting at
Cutchogue vacation rentals start at G$31,364 GYD per night before taxes and fees

Verified guest reviews
Over 1,910 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Vacation rentals with a pool
30 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 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!
Top-rated house rentals in Cutchogue
Guests agree: these houses are highly rated for location, cleanliness, and more.

Cozy Farmhouse Retreat in North Fork, NY
A 1905 farmhouse with modern touches, Arthur's Vineyard is a cozy 3-bed, 2-bath home in walking distance of Greenport village's beaches, marina, restaurants and boutiques. An open plan living area, breezy decor and a large landscaped backyard for spending relaxed summer days and nights with your family and friends, including the 4-legged ones. Walk to the train station/jitney or take a short drive to the wineries & farm stands of the North Fork. Recent updates: central heat/AC & new bathrooms.
FamilyValueParking

Waterfront Beach Cottage
Renovated New Suffolk Waterfront Beach Cottage steps from water/beach/restaurants & more w/ water views from practically every window in the heart of the most special neighborhood in the north fork. Perfect for families with twn over full bunks, pvt mstr, grill, outdr shower and new kitchen. Bonus room has comfy couches & sunset views. Dine al fresco with water views or stroll to restaurants, apple picking or famous New Suffolk beach. Minutes from everything your vacation could need, year round.
ValueFamilyComfort

Nassau Point, North Fork Home w/ Pool
Whether you are looking for lots of outdoor space for the kids to explore, bike, play at the beach or splash around in the pool OR you are looking to explore all of the 38 Vineyards along Long Islands, this house is perfect for you. Open kitchen, dining and living space which then opens up to the deck and pool. 4 bedrooms, sleeping 8 comfortably. Two of the bedrooms are connected with a thru-door. Gated swimming pool. Minutes from the local sandy beach. Rental Permit: HMT24-00101 14-Day minimum
LocationFamilyNearby

Aqua Vista
100% Walking Score 1 block away from Village 3 blocks away from Beach. 1 block away from Shelter Island Ferry. Around the corner from Hampton Jitney & LIRR Newly-renovated 2-family Home! This rental is 2nd floor apartment (only). Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy. Located right in Greenport. Walking distance to all the restaurants, bars, shopping, coffee shops.
LocationValueAmenities

Stunning Hamptons Waterfront Escape w/ Sunset View
Experience an unforgettable trip in the Hamptons at our waterfront haven! Savor the views and sunset from our spacious deck. Vaulted ceilings and large windows flood the space with natural light. Brand new Weber Grill (2025). We have completed renovations of 3 bathrooms, 2 kitchens, and the entire pool house over the last 18 months. Our home is <10 minutes drive to the beach, groceries, and restaurants! Our pool will close on September 15th, 2026 and will reopen May 29, 2027.
ValueFamilyLaundry

Walk to Beautiful Beach in Heart of Wine Country
Enjoy bright, comfortable and modern home in the heart of North Fork wine and farm country located just a quick walk from a gorgeous Peconic Bay beach with tennis/pickleball courts, volleyball and playground right on the beach. You'll have easy and quick access to the best of the east end: beautiful beaches, boating, fishing, fine and casual dining, vineyards, wineries, breweries, farms and farm stands offering fresh local produce, antique and local shops.
ValueFamilyHeating

Modern Farmhouse Steps to Beach & Love Lane
Our home is professionally designed and set on a spacious, manicured green parcel enclosed by a Cul-de-sac with complete privacy inside and out. The home is designed with all modern conveniences and is located less than a 5 minute walk to Love Lane (Mattituck's charming downtown), Veteran's Beach (one of the best beaches on the Northfork) and the Mattituck train station. It is a place to relax, unwind and enjoy all that North Fork has to offer.
LocationValueParks

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.
FamilyValueIndoor spaces

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong
Beachy casual feel-good home easily located at the entrance to The Hamptons. Lovely views of Bay, Nightly Sunsets & birds! Launch our Kayaks at street's tiny beach flowing from Cold Spring Pond into Bay. Or cuddle by the fireplace and play our many available games. We provide soft sheets & towels for the showers and & beach...priding ourselves on your comfort! Our Private-Pool is heatable & plant-surrounded with Outdoor Shower.
LocationValueOutdoor spaces

NoFo Getaway: Pool, Farm Views, Beach Sunsets
Our family friendly home is set on a spacious green parcel, abutting a farm and the ocean with a pool, outdoor shower, large deck, stone firepit, pool shed, children's custom built playground, lawn games and more. Central air is installed throughout. The home features 4 bedrooms, 3 full bathrooms, 1 half bathroom and an outdoor shower. FOR VIRTUAL TOUR OR VIDEO TOUR PLEASE EMAIL AND WE WILL PROVIDE
LocationFamilyKitchen

Sag Harbor Cottage, Walk to the Beach!
Renovated to perfection, this fully equipped fresh & modern beach cottage has an open-plan living room, dining room & kitchen, all with high ceilings, immaculate finishings, & a sunny lower level TV room. A broad mahogany deck with large outdoor shower & gas BBQ grill runs the full length of the house & overlooks a roomy lawn with great privacy, fire pit and mature landscaping.
ValueLocationComfort

Walk to Breakwater Beach in Heart of Wine Country
Private and peaceful cottage walking distance to Breakwater Beach and Old Mill Inn Restaurant on the water opening Spring 2025. There are two large decks to relax by the firepit and drink your wine from the local wineries. Bikes, kayak, and paddle board are stored in the barn for guests use. Easy access to the marina, fishing, fine dining, vineyards, and farm stands.
LocationFamilyIndoor spaces
Popular amenities for Cutchogue house rentals
House rentals with a pool

Beach Barn w/ Heated Pool & Sauna - Dog Friendly
LocationFamilyCheck-in

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)
FamilyLocationGrill

Family Retreat with Heated Pool, Hot Tub, Sauna.
ValueLocationLayout

Coastal Retreat|Heated Saltwater Pool|5 MinToBeach
FamilyLocationBackyard

Astounding Watermill 5 Bedroom home with Pool
ValueLocationCheckout

Stylish+Modern Cape w/Saltwater Pool-5min to Beach
FamilyValueHeating

Serene East Hampton Escape - Warm Pool til Nov
FamilyLocationCheckout

Serene + chic ~ 8 mins to Main Street + beaches
LocationFamilyCleanliness
Weekly house rentals

Beautiful 1930s 4 bed 3 bath! Walk to Beach
FamilyLocationBathroom

Wine Country Home
LocationValueParking

Sunny Harbor Suite
ValueLocationAmenities

Le Petit Cottage Southold NY
LocationValueComfort

Country Beach Home!
LocationFamilyNearby

Brand New Charming Beach House
LocationFamilyCleanliness

Coastal Cottage on the Water
LocationFamilyHospitality

Water Front Ospreys Nest Beach Rights Permit #1310
FamilyLocationIndoor spaces
Private house rentals

Stylish Beach Getaway: pool & walking location
FamilyLocationTV

Mattituck Hideaway/ Luxury Wine Country Retreat
ValueFamilyHospitality

North Fork Sound Front Home with Pool
FamilyLocationOutdoor spaces

Peconic Pearl Cottage
FamilyDecorPool

Greenport walk to beach & vineyard! Brand new home
LocationFamilyKitchen

Sprawling Modern Home Minutes from Beach
FamilyLocationQuiet

The Saltbox: Outdoor Dining, Fire Pit, Soaking Tub
LocationFamilyWalkability

Corwin House
LocationFamilyGetting around
When is the best time to visit Cutchogue?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$99,319 GYD | G$125,456 GYD | G$112,283 GYD | G$112,283 GYD | G$122,320 GYD | G$144,484 GYD | G$156,820 GYD | G$153,684 GYD | G$122,738 GYD | G$104,547 GYD | G$120,020 GYD | G$104,756 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 |
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