Pet-friendly holiday rentals in Cutchogue

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.

4.94 out of 5 average rating, 72 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.

PetsOutdoor spacesGetting around

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

Outdoor spacesWalkabilityKitchen

4.85 out of 5 average rating, 155 reviews

Hamptons Oceanfront Oasis

Escape the hustle & bustle of city life and unwind at this stunning home in the Hamptons. The oceanfront oasis is the perfect way to wake up to ocean views, beaches and nearby restaurants. Relax on our spacious deck - perfect for morning coffees & sunset cocktails. It is just a short drive to the train station & only 15 minutes from the airport for quick getaways. For your safety, the home is equipped with Ring cameras and one-use key codes. Book now and experience the ultimate Hamptons escape!

WalkabilityOutdoor spacesSleep quality

4.89 out of 5 average rating, 9 reviews

Apartment in Southold

Kenney's Beach Loft - Vineyards, Horton Lighthouse

Kenny’s Beach Loft is a cozy, pet-friendly open-concept queen bed studio with 1 bathroom, a kitchenette, comfortable living and dining area, in-unit washer and dryer, and a private patio. Perfect for families and couples getaway. Just steps from Kenney’s Beach for stunning sunsets and peaceful walks. Minutes to Southold Fish Market, Croteaux Vineyards, Horton Point Lighthouse, and North Fork wineries for dining, wine tasting, and exploring. Enjoy coastal charm, seaside air, and total serenity.

Outdoor spacesWalkabilityIndoor spaces

4.98 out of 5 average rating, 180 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.

Outdoor spacesWalkabilityNearby

Apartment in Hampton Bays

A calm waterfront scene shows a serene body of water reflecting the sky. A sandy beach is visible, framed by natural vegetation, with a wooden barrier along the shoreline. The peaceful setting invites relaxation and enjoyment of the outdoors.

4.97 out of 5 average rating, 433 reviews

Private & Cozy Cottage with short walk to beach!

Walking distance to Bay Beach & Rumba, & short drive to town & ocean. Quiet neighborhood, great for couples, King bed upstairs, bit of a steep staircase, so may not be suited for anyone with mobility challenges. Kayaks, paddle-boards, available to enjoy. Dog friendly with fenced in patio and doggy door. Private outdoor patio, with charcoal grill. A/C & Heat for year-round enjoyment. Easy to get in/out from the city. Close drive to visit Westhampton and Southampton Main Streets.

Outdoor spacesPetsValue

4.87 out of 5 average rating, 122 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

Welcome to nature's retreat, our secluded North Fork haven where 2+ acres of wild beauty and private beach access promise unparalleled relaxation. Delight in our hot tub's warmth under the stars, unwind on swings, or glide on bay waters with our kayak. With enchanting porch views, an invigorating outdoor shower, and nearby organic farms, our cabin is an idyllic escape. Experience the local charm with vineyard tours and return to a haven of comfort and adventure.

PetsWalkabilityHiking

4.92 out of 5 average rating, 177 reviews

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.

Home in Mattituck

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.

WalkabilityOutdoor spacesBathroom

4.98 out of 5 average rating, 55 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

Cottage 1 sits in a beautifully maintained garden compound just one minute from private sandy beaches on Peconic Bay. Quaint New Suffolk is among the most coveted hamlets with notable beaches on the North Fork. Come for spring blossoms, summer beaches or autumn harvest. Enjoy wine tastings at nearby world class vineyards and best of market locally grown produce, farm to table dining, fresh fish markets, orchards and miles of scenic vineyards.

PetsWalkabilityNearby

4.95 out of 5 average rating, 393 reviews

A bright living room features a comfortable gray sofa against a neutral wall, complemented by a light-colored rug with geometric patterns. A wooden coffee table sits in front, with a lounge chair nearby. Natural light enters through multiple windows, creating a spacious feel.

Home in Greenport

The Sandpiper

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 is for rental of 1st floor apartment (only) plus cabana, plus outdoor jacuzzi. Close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place! Incredible location, safe, cozy.

PetsOutdoor spacesView

4.92 out of 5 average rating, 115 reviews

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.

Home in Mattituck

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.

WalkabilityPetsIndoor spaces

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, 209 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.

Outdoor spacesWalkabilityQuiet

Popular amenities for Cutchogue pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A large pool is surrounded by a well-maintained lawn, featuring shallow lounging areas and sleek white loungers. A shaded gazebo can be seen in the background, offering a space for relaxation, while trees and greenery add to the tranquil outdoor setting.

4.93 out of 5 average rating, 46 reviews

North Fork Extended-Stay Retreat, Pool, Beaches

Outdoor spacesWalkabilityIndoor spaces

4.88 out of 5 average rating, 24 reviews

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

Stylish Beach Getaway: pool & walking location

Outdoor spacesWalkabilityLayout

Superhost

Home in Southold

4.8 out of 5 average rating, 15 reviews

Peconic Sound Beach Cottage | Walk to Sound

PetsWalkabilityLocation

Superhost

A well-lit living area features a large window and a glass door leading to the outdoor space. A modern fireplace is centered in the room, complemented by stylish furniture, including a curved sofa and a standing lamp. Art decor adds visual interest to the wall.

4.81 out of 5 average rating, 42 reviews

Stylish Getaway in Greenport

PetsWalkabilityDecor

4.95 out of 5 average rating, 263 reviews

A serene sunset is captured over the bay, with warm hues reflecting on the water's surface. Silhouettes of wooden posts emerge from the calm waves, creating a tranquil atmosphere. The horizon showcases a mix of colors as the day transitions to evening.

Home in Springs

Private beach, fully updated house, on 2 acres.

Outdoor spacesPetsSleep quality

4.94 out of 5 average rating, 332 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 -

WalkabilityOutdoor spacesCondition

4.92 out of 5 average rating, 106 reviews

A bright living area is furnished with a leather sofa and a dark coffee table, positioned on a textured rug. Natural light filters through large windows, illuminating the space. A staircase leads to an upper level, with wooden accents enhancing the modern design.

Home in Bridgehampton

Pool Central Private Bridgehampton Home

PetsOutdoor spacesBeach

4.92 out of 5 average rating, 130 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

Outdoor spacesPetsParking

Pet-friendly home rentals with a pool

4.98 out of 5 average rating, 62 reviews

Corwin House

WalkabilityOutdoor spacesLocation

4.93 out of 5 average rating, 136 reviews

A spacious backyard is highlighted by a blue in-ground pool surrounded by lounge chairs. Red umbrellas provide shade, while a tall wooden fence adds privacy. Lush green grass complements the natural setting, and a rustic home is visible in the background among the trees.

Home in Springs

Private & Pristine with Pool and Kid’s Playard

PetsOutdoor spacesGetting around

5 out of 5 average rating, 41 reviews

3Bed/2 Bath - Hamptons Getaway w/ Heated Pool!

WalkabilityOutdoor spacesCheckout

4.96 out of 5 average rating, 106 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

PetsOutdoor spacesValue

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.

4.97 out of 5 average rating, 150 reviews

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

PetsWalkabilityAmenities

A spacious balcony extends along the side of the house, offering unobstructed views of the shimmering water. Weathered wooden benches provide seating, while the gentle waves can be observed lapping against the shore in the distance.

4.89 out of 5 average rating, 44 reviews

North Fork Sound Front Home with Pool

PetsOutdoor spacesGetting around

4.97 out of 5 average rating, 79 reviews

A spacious lawn is bordered by tall trees, providing a natural frame for the cottage. The vibrant green grass leads to a serene waterfront, where the lake reflects the sunlight. The peaceful setting invites relaxation and outdoor activities.

Cottage in Water Mill

Head of Pond House - Waterfront Cottage

Outdoor spacesPetsAccuracy

4.95 out of 5 average rating, 201 reviews

A serene view of calm water featuring kayakers enjoying a sunny day. The distant shoreline is dotted with houses, creating a relaxed coastal atmosphere. Clear blue skies reflect on the water, enhancing the peaceful scene.

Home in Shinnecock Hills

Southamp Waterview, DogsFREE! Kayaks, Ping-Pong

WalkabilityPetsLocation

Private, pet-friendly home rentals

4.91 out of 5 average rating, 43 reviews

Lakefront NoFo Cottage, walkable to public beach

WalkabilityOutdoor spacesCleanliness

4.86 out of 5 average rating, 28 reviews

A charming beach cottage is set against a clear blue sky, featuring a welcoming enclosed front porch. Surrounding gardens are filled with vibrant pink and purple flowers, framing the path leading to the front door and adding to the property’s tranquil ambiance.

Cottage in North Fork

Charming Beach Cottage, Vineyards & Sunset Views

PetsOutdoor spacesKitchen

4.98 out of 5 average rating, 41 reviews

A softly lit path of stone pavers leads to a furnished patio area, where a dining table and chairs are set under a vibrant red umbrella. Trees provide shade, and gentle garden lights illuminate the surrounding grass, creating a welcoming evening ambiance.

Home in Mattituck

Vineyard Views & Bike to the Beach

WalkabilityOutdoor spacesCleanliness

4.91 out of 5 average rating, 87 reviews

A sunlit living area features a light-colored sofa accented with blue pillows. A coffee table sits in front, and a ceiling fan adds comfort. Large windows provide views of greenery outside, while a side table with a lamp enhances the cozy ambiance.

Guesthouse in Southold

Southold- Adorable 1 Bedroom Cottage

Outdoor spacesWalkabilityTV

A charming cottage-style home is set amid lush greenery, featuring a covered porch with white railings. A gravel pathway leads to the entrance, surrounded by manicured shrubs and a well-kept lawn. The exterior is finished with natural wood siding and a sloped gray roof.

5 out of 5 average rating, 7 reviews

Hamptons Waterview Cottage

Outdoor spacesWalkabilityIndoor spaces

4.93 out of 5 average rating, 73 reviews

An aerial view captures the serene landscape of a coastal area, showcasing a blend of residential homes and natural beauty. The water glistens under the sunlight, with sailboats dotted along the horizon, creating a peaceful atmosphere. Trees and green spaces provide a calming ambiance.

Home in Greenport

Walk to Beach and Greenport Village, Two King Beds

PetsOutdoor spacesParks

Superhost

Home in Shinnecock Hills

4.86 out of 5 average rating, 73 reviews

Chic Southampton Home. Mins to Village and Beach!

PetsWalkabilityCheckout