Family-friendly holiday rentals in Cutchogue

A spacious living area is illuminated by natural light from skylights and large windows. A soft sofa is positioned on a light-colored rug, accompanied by a round pouf. Dining space is visible in the background, showcasing a simple wooden table and chairs.

4.95 out of 5 average rating, 87 reviews

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

KitchenIndoor spacesCleanliness

The exterior of a renovated cottage is displayed, featuring light green siding and white trim. Large windows invite natural light, while a welcoming front porch is framed by greenery. A gravel pathway and well-maintained landscaping enhance the peaceful setting.

5.0 out of 5 average rating, 28 reviews

Beautiful 1930s 4 bed 3 bath! Walk to Beach

Beautiful 1930s fully renovated cottage with 4 gorgeous bedrooms & 3 full baths. Spacious outdoor living space including an outdoor shower & fire pit. 1 block from a beautiful life guarded, sandy bay beach. Relax with the family at this peaceful place to stay in exclusive Fleets Neck and close to multiple spectacular wineries, breweries, farms, shopping outlets and worldclass restaurants. Stunning waterscapes abound! Enjoy a country retreat in a slice of heaven! Southold town permit 1137

KitchenIndoor spacesDecor

4.94 out of 5 average rating, 156 reviews

Guest suite in Southold

Comfortable Suite, a walk to the beach

Keep it simple at this spacious and peaceful home. Built in 2019, this home was specially designed for sustainable, green living; ground-source heating, and super insulation allow for minimal environmental impact and provide a quiet and comfortable stay. About a five minute walk to McCabe’s Beach. Very near to wineries, farms, and the quaint shops and bakeries of Southold and Greenport. Little Fish restaurant and oyster sales all down the street. Short drive from Sparkling Pointe vineyard.

FamilyKitchenBeach

4.91 out of 5 average rating, 201 reviews

Home in Sag Harbor

Barefoot Bliss | Quiet Family Retreat Heated Pool

Welcome to your Hamptons retreat. This bright single-level home sits in a quiet neighborhood just minutes from Main Street and the ocean. The private fenced yard overlooks a peaceful nature preserve and features a heated pool (June–Sept, heating available for a fee), hot tub, outdoor fireplace, and outdoor shower—perfect after a beach day. Family-friendly amenities include a sandbox, toys, crib, and highchair, with a separate safety fence surrounding the pool for added peace of mind.

KitchenFamilyLong stay

4.98 out of 5 average rating, 182 reviews

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

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.

Indoor spacesFamilyWi-Fi

Guest suite in North Fork

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.

4.93 out of 5 average rating, 123 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.

Indoor spacesFamilyGetting around

A modern living area is highlighted by a gray sofa centered on a low coffee table. Two armchairs are placed to one side, while a textured area rug complements the space. Wall art hangs above the sofa, and natural light enters through large windows.

4.96 out of 5 average rating, 166 reviews

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.

FamilyKitchenTV

A bright living area features light-colored walls and wooden flooring. A comfortable sofa and a plush chair are arranged around a rustic coffee table. A ceiling fan hangs above, while a kitchen with a blue island is visible in the background, enhancing the space's openness.

4.92 out of 5 average rating, 178 reviews

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.

KitchenFamilyHospitality

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.

4.97 out of 5 average rating, 218 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.

KitchenFamilyAir conditioning

A modern cottage is set amidst lush greenery, featuring a spacious rear deck and a lower patio area with two lounge chairs. The second story includes a covered deck with an awning, while large windows invite natural light into the interior.

4.92 out of 5 average rating, 116 reviews

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.

KitchenIndoor spacesLayout

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.

4.96 out of 5 average rating, 214 reviews

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.

Indoor spacesKitchenWi-Fi

Guest suite in North Fork

The exterior of a historic Tudor home is shown, featuring a blend of brick and wood accents. A winding driveway leads to the entrance, surrounded by lush greenery and a decorative black fence. Trees provide shade, enhancing the serene outdoor setting.

4.88 out of 5 average rating, 744 reviews

Walk to Vineyards, Beaches, Farms & Town

Private bungalow with a separate entrance in a historical tudor home. Spacious bedroom with king-sized bed, kitchenette and bathroom. Two bikes, cable TV, internet, AC, beach towels, parking, snacks, coffee and water all provided. Walking distance to the beach, restaurants, shops, vineyards, grocery, farms and fish market. Jitney stop is one block away!

KitchenIndoor spacesDecor

Popular amenities for Cutchogue family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 109 reviews

A vibrant pool scene is captured, featuring a colorful unicorn float positioned on the water. Lush hydrangea blooms frame the area in shades of pink, complementing the surrounding greenery and the wooden fence that provides privacy.

Apartment in Southampton

Swimming pool w/Hot tub Fire Pit Coffee Bar

FamilyKitchenBiking

4.87 out of 5 average rating, 124 reviews

A spacious living area features exposed wooden beams and a cozy brick fireplace. Comfortable seating includes a brown sofa and recliner, with decorative pillows adding warmth. A glass coffee table stands on a colorful area rug, while large windows overlook the greenery outside.

Cabin in North Fork

Beach & Woods: Cozy Cabin, Hot tub, Peloton, Oh My

KitchenIndoor spacesAccuracy

4.92 out of 5 average rating, 513 reviews

A spacious living area features a dark leather sofa adorned with colorful throw pillows, complimented by a patterned area rug. A ceiling fan is positioned above, and natural light streams through multiple windows. An adjoining dining area with a black table and chairs is visible.

Home in Greenport

Blue Bay Dream (Outdoor Jacuzzi, Cabana + Office)

Indoor spacesFamilyAmenities

4.99 out of 5 average rating, 211 reviews

A screened-in patio features a wooden ceiling and overhead fans, providing a comfortable space for relaxation. A navy blue sofa pairs with a coffee table, while tall chairs surround a dining table. Views of a spacious yard and trees are visible through the screens.

Home in Greenport

Greenport Village walking distance to all

Indoor spacesKitchenLayout

4.96 out of 5 average rating, 184 reviews

Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

Indoor spacesKitchenAir conditioning

4.99 out of 5 average rating, 108 reviews

Home in Branford

Steps to Beach • Hot Tub • Game Room • Water Views

FamilyIndoor spacesHospitality

4.92 out of 5 average rating, 144 reviews

A modern farmhouse is set on a spacious lot. The architecture features a blend of dark and light siding with a white chimney. A well-maintained path leads to a front porch, surrounded by landscaped greenery, enhancing the inviting curb appeal.

Home in Sound Beach

Luxury modern farmhouse with heated pool & hot tub

Indoor spacesKitchenTV

Superhost

A crystal-clear swimming pool is surrounded by a landscaped garden featuring lush greenery and blooming flowers. Natural stone patio borders the pool, offering space for lounging and relaxation in a private setting nestled among trees.

Home in East Hampton

4.98 out of 5 average rating, 144 reviews

Explore the Water & Woods at a Relaxing Retreat

KitchenFamilyCleanliness

Family- and pet-friendly home rentals

4.94 out of 5 average rating, 166 reviews

A well-maintained outdoor pool area is surrounded by a wooden deck and lush greenery. Lounge chairs are positioned along the pool, with a shaded area provided by a large tree. The clear blue water of the pool reflects the sunlight, inviting relaxation.

Home in Water Mill

Astounding Watermill 5 Bedroom home with Pool

Indoor spacesKitchenAccuracy

4.91 out of 5 average rating, 141 reviews

Home in Springs

Serene w/ large pool ~1 block to waterfront dining

Indoor spacesKitchenParking

4.97 out of 5 average rating, 153 reviews

A heated saltwater pool is surrounded by a spacious green lawn and lounge chairs, with a tree-lined white fence in the background. The house features a charming design with large windows and a wide patio area, suitable for outdoor dining and relaxation.

Home in Hampton Bays

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

Indoor spacesFamilyAir conditioning

4.94 out of 5 average rating, 334 reviews

An enclosed outdoor living space features a wooden deck overlooking a heated pool. Furnished with a large round table and comfortable seating, natural light floods through the screens, creating an airy atmosphere. Elegant trees and lounge chairs visible outside enhance the serene environment.

Home in Bridgehampton

Amazing Home close to Everything -

FamilyIndoor spacesLocation

4.99 out of 5 average rating, 177 reviews

Cottage in Guilford

"Red House on the Knoll" at Indian Cove

FamilyKitchenBathroom

4.92 out of 5 average rating, 132 reviews

The exterior of the farmhouse is framed by well-maintained hedges, with a simple wooden staircase leading to the front door. Brightly lit windows are positioned symmetrically, highlighting the home's classic architecture. The surrounding greenery complements the inviting entrance.

Home in Greenport

Cozy Farmhouse Retreat in North Fork, NY

KitchenFamilyBarbecue

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.

4.95 out of 5 average rating, 74 reviews

Waterfront Beach Cottage

KitchenIndoor spacesValue

4.98 out of 5 average rating, 56 reviews

A charming cottage exterior is surrounded by vibrant roses and lush greenery. A welcoming porch is visible, leading to the entrance. A well-maintained lawn of lush grass provides a pleasant approach, with sunlight filtering through the trees above.

Cottage in North Fork

New Suffolk Beach Cottage 1 | North Fork

KitchenFamilyWalkability

Family-friendly home rentals with a pool

4.89 out of 5 average rating, 198 reviews

The living area features a spacious dark gray couch, a light wooden coffee table, and a white dining table with woven chairs. Natural light filters through the window with plantation shutters, while decorative elements like a round mirror and wall art create a welcoming ambiance.

Condo in Greenport

Beautiful Waterview Condo on the North Fork of LI

KitchenIndoor spacesHospitality

4.89 out of 5 average rating, 281 reviews

An expansive view of the ocean under a bright blue sky, featuring wispy clouds. The shoreline is lined with gentle waves, and a grassy area is visible in the foreground, leading down to the water.

Condo in Greenport

Sound Front Condominium

KitchenFamilyQuiet

Superhost

A living room features a light-colored sofa against a neutral wall, complemented by a striped area rug. A wall-mounted TV and decorative elements, including a mirror and wall hooks, enhance the space. Soft lighting is provided by two standing lamps, creating a welcoming environment.

Condo in Greenport

4.88 out of 5 average rating, 170 reviews

Waterfront Escape | Private Beach, Pool & Views

KitchenFamilyBarbecue

Home in Westhampton Beach

A charming cottage exterior features wood shingles and white trim. An American flag hangs proudly from the front, while window boxes with greenery add a touch of color. The light blue front door complements the natural elements, inviting guests inside.

4.98 out of 5 average rating, 173 reviews

Luxury Hamptons Home with Heated Saltwater Pool

Indoor spacesFamilyCheckout

Superhost

A bright living area features large windows that offer views of the nearby pond. Comfortable seating includes a white sofa, patterned chairs, and a coffee table, all arranged on a natural fiber rug. Light from the windows enhances the serene atmosphere.

Home in Sag Harbor

4.86 out of 5 average rating, 137 reviews

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

FamilyIndoor spacesCheckout

5.0 out of 5 average rating, 10 reviews

Serene and refined North Fork home with pool

FamilyKitchenBackyard

A clear view of a gunite pool reveals crystal blue water, surrounded by a spacious lawn. Four lounge chairs are positioned nearby, and the house is seen in the background, framed by lush hedges and trees, with a deck that offers steps leading up to the entrance.

4.94 out of 5 average rating, 53 reviews

North Fork Farmhouse with Saltwater Pool

KitchenFamilyAccess