Holiday houses in Cutchogue

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Top-rated holiday rentals in Cutchogue

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
The exterior of the cottage is highlighted by a well-maintained yard featuring a lush green lawn. A patio area with seating is visible, surrounded by flowering shrubs and trees. Multiple large windows offer a view into the inviting living spaces within.
Home in New Suffolk
4.94 out of 5 average rating, 54 reviews

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.

Guest favourite
A private pool area is shown with a clear blue swimming pool surrounded by four lounge chairs. A charming shed is situated in the background, framed by green trees and landscaped gardens.
Home in Southold
4.9 out of 5 average rating, 20 reviews

Stylish Beach Getaway: pool & walking location

Perfectly located within walking distance to shops, beaches, and restaurants, our designer home offers comfort, luxury amenities, and privacy. Interested in a long term rental? Message us! Enjoy a beautifully landscaped backyard with pool, chefs kitchen for hosting, and nearby beach farms & wineries. Bedrooms boast organic linens and bathrooms offer Bathing Culture products. Kitchen is stocked with local organic pantry staples and stainless steel appliances to cook or grill on the patio.

Guest favourite
A serene landscape features a heated saltwater pool bordered by lush greenery. Sun loungers are positioned around the pool under umbrellas, while a wooden fence with trees creates a peaceful backdrop, enhancing the outdoor relaxation space.
Home in Mattituck
4.92 out of 5 average rating, 115 reviews

Modern farmhouse w/ pool, beach, horses and winery

A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Top Guest favourite
A modern kitchen is presented with sleek cabinetry and stainless steel appliances. A large island with a marble countertop is surrounded by several cushioned stools. Natural light floods in from a nearby window, illuminating a small vase of blue hydrangeas on the island.
Cottage in North Fork
5 out of 5 average rating, 49 reviews

Renovated 2-Bedroom Cottage on the North Fork

Serenity awaits as you step into this totally renovated Cottage. The property is perfectly located in the heart of Long Island's Wine Country. Centered on the North Fork this home allows you to explore all that there is to offer…. antique shops, restaurants, vineyards, breweries, farm stands and the beautiful Causeway Beach is just steps from this home. The home is newly renovated with a new kitchen, appliances, new bathroom, outdoor gas grill, fire pit and a beautiful screened in porch.

Guest favourite
The modern kitchen features sleek white cabinetry and stainless steel appliances, including a refrigerator. A black island with seating faces a dining area, illuminated by natural light from large windows. Light-colored marble flooring extends throughout, creating an open and airy feel.
Cottage in North Fork
4.95 out of 5 average rating, 20 reviews

Exceptional! Modern Farm House by the beach

Enjoy a stylish experience at this centrally-located modern cottage. Make yourself at home this summer in this newly renovated cottage. Its down the road from a private Fleet’s Neck Beach as well as in the heart of beautiful NorthFork wine country! Guests can enjoy easy travel through the NorthFork and all it has to offer! Close to the Long Island Railroad for easy travel into the city. Enjoy your stay visiting local farms,restaurants,beaches, vineyards, breweries and seasonal festival

Top Guest favourite
A light-filled living space is highlighted by a wall of glass, providing expansive views of the water and a natural landscape. The space includes a round coffee table on a light floor, with comfortable seating arranged to enjoy the serene outdoor scenery.
Cottage in Riverhead
4.98 out of 5 average rating, 167 reviews

Savor Ocean Sunsets at a Soothing Beachfront Haven

Newly renovated and featured as a top Airbnb by New York Magazine, The Beach Cottage has been designed and decorated in a modern organic style, with a palette of whites and neutrals to create a serene and peaceful escape. Relax in the airy, light and open living room, which features a wall of glass for indoor/outdoor living with expansive, uninterrupted water views. Stay on the property for swimming, beach walks, sunsets and BBQs - or venture out to enjoy all the North Fork has to offer.

Guest favourite
A cozy bedroom featuring a spacious bed dressed in soft linens is positioned against a light-colored wall. Natural light filters through two windows, casting gentle shadows on the warm wooden floor. A ceiling fan hangs overhead, and a mirror and chair add functional elements to the space.
Home in North Fork
4.97 out of 5 average rating, 184 reviews

Secluded Farmhouse - Studio Apartment Style Unit

Beautiful, quiet, studio apartment-style unit (private entrance w/full bath) tucked away in a modern farmhouse on a gorgeous, secluded North Fork farm. Guests have exclusive use of screen porch, fire pit, bbq and outdoor seating area. Jess is a private chef and yoga instructor, so be sure to inquire for services! Private hiking trails, fresh eggs, produce from garden, beach gear, Keurig, mini fridge, homemade granola, tea. Fresh eggs, seasonal veg from the garden, and meals (inquire!)

Guest favourite
A spacious farmhouse is showcased, featuring a welcoming porch with an American flag. The exterior is adorned with dark wooden shingles and large windows. Lush green lawn and well-maintained flower beds enhance the inviting curb appeal under a clear blue sky.
Home in North Fork
4.96 out of 5 average rating, 106 reviews

Stunning Farmhouse in NoFo I Heated Pool, Wineries

Chic & Luxurious North Fork Farmhouse Retreat Set on a private 1-acre lot, this stylish farmhouse offers a pool, lounge areas, and refreshing ocean breezes. Just 1.5 hours from NYC, you’ll be minutes from beaches, wineries, farm stands, hiking, and golf. Inside, enjoy modern interiors, a full kitchen, and fast Wi-Fi. Perfect for families, couples, or friends, this retreat is ideal for a peaceful escape, remote work, or exploring wine country near the Hamptons and North Fork.

Top Guest favourite
A serene beach scene is depicted, showcasing soft white sand bordered by gentle waves. Tall grasses sway in the foreground, framing the clear blue water that extends to the horizon, providing a sense of calm and natural beauty.
Guest suite in North Fork
4.93 out of 5 average rating, 112 reviews

Enjoy a relaxing getaway to the North Fork

One bedroom suite, with separate entrance in quiet Nassau Point; a peninsula, surrounded by beaches. Nassau Point is a great place to bike, walk and enjoy nature. Fully functioning WiFI for guests looking to extend their stay, while working from home. Fishermen's beach is a 5 minute walk Causeway beach is a 10 minute walk with parking. Point beach, 1.5 mile walk, a Southold Parking Permit required. You will find 20 wineries within 5 miles, just a short Uber ride away.

Guest favourite
A serene outdoor area showcases a saltwater pool with a spa, surrounded by well-maintained landscaping featuring vibrant yellow flowers. Lush green fields extend into the distance, framed by a clear sky with scattered clouds.
Home in North Fork
4.97 out of 5 average rating, 212 reviews

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.

Top Guest favourite
A charming house with a white exterior features a vibrant red front door. Large windows allow natural light to illuminate the entryway. A small staircase leads up to the door, surrounded by greenery and a well-maintained lawn.
Home in North Fork
4.97 out of 5 average rating, 38 reviews

North Fork Farm House

This home is located on the North Fork of Long Island in the heart of wine country. We have a beautiful winery within close walking distance. We are surrounded by beautiful beaches and a short ferry ride to Shelter Island. There’s great restaurants and shopping just 15 minutes east in the town of Greenport or 5 minutes west to Love Lane in Mattituck. There is also lots to do in the town of Riverhead, including shopping at Tanger Outlets.

Top Guest favourite
A serene waterfront scene captures a vibrant sunset reflecting on calm waters. Silhouetted trees line the background, while a private dock extends into the water, featuring a railing. Warm hues of orange and pink fill the sky, creating a peaceful ambiance.
Cottage in North Fork
4.98 out of 5 average rating, 55 reviews

Stunning waterfront modern farmhouse with dock.

Relax with the whole family or a group of friends at this peaceful, waterfront cottage. Perfect spot to bring a group for a country retreat in the heart of stunning vineyards, spectacular restaurants and stunning waterscapes. Our home’s interior is beautifully appointed where you will be comfortable both inside and outside on our patio, or deck with a breathtaking waterfront view. Peaceful, relaxing and magical place in an idyllic spot.

Popular amenities for Cutchogue holiday rentals

When is the best time to visit Cutchogue?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Cutchogue?

    Cutchogue has more than 110 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cottage rentals in Cutchogue?

    Experience the best of Cutchogue with our cottage rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Cutchogue?

    Four-legged friends are welcome in Cutchogue. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Cutchogue?

    Yes! Work meets play with ease at over 60 vacation rentals in Cutchogue featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Cutchogue house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 house rentals with pools in Cutchogue, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Cutchogue?

    Make yourself at home in Cutchogue by choosing from our most frequently booked neighborhoods. We have over 300 vacation rentals in Cutchogue, over 110 vacation rentals in New Suffolk, and over 200 vacation rentals in Peconic.

  • Do house rentals in Cutchogue have air conditioning?

    Absolutely! We offer over 90 house rentals with air conditioning in Cutchogue. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Cutchogue have a kitchen?

    Absolutely! We offer over 10 cottage rentals with a kitchen in Cutchogue. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cutchogue have wifi?

    Absolutely! We offer over 100 house rentals with wifi in Cutchogue. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Cutchogue have free parking?

    Absolutely! We offer over 90 house rentals with free parking in Cutchogue. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Cutchogue

  • Total holiday rentals

    Explore 130 holiday rentals in Cutchogue

  • Nightly prices starting at

    Cutchogue holiday rentals start at $141 AUD per night before taxes and fees

  • Verified guest reviews

    Over 4,200 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    130 of Cutchogue holiday 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!

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