Holiday rentals with outdoor seating in Baiting Hollow

4.87 out of 5 average rating, 103 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!

4.88 out of 5 average rating, 536 reviews

A serene beach scene illustrates a vast stretch of shoreline, with gentle waves lapping at the sand. The water is a mix of blue and green hues under a clear sky, providing a calming seaside atmosphere.

Cabin in Rocky Point

Great little place just for a couple

The outdoor courtyard is especially nice and private ,with a fire pit, grill and comfortable chairs. It is a rustic location easy walking distance to North Shore Beach. If you want an ocean beach you can drive straight south for 20 minutes and reach Smiths Point State Park right on the ocean. The North Fork with its vineyards is a short drive and the Hamptons also only 30 minutes to West Hampton. You can fish, golf, walk among the wooded area and relax in peace. A pleasure. linen 100% cotton.

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.

4.93 out of 5 average rating, 102 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.

4.75 out of 5 average rating, 174 reviews

Flat in Ridge

The Silver Pine Cone

Welcome to the hamlet of Ridge. The gateway to Long Islands many treasures. Whether you are venturing out to the North Fork wineries or a scenic drive on the south shore beaches on your way to the Hamptons. A beautiful cozy private (not a shared space) full one bedroom downstairs lower level apartment, living room w/full size sofa sleeper, kitchen/dining room, full bathroom and a completely separate yard with patio furniture exclusively for your use. Everything you need to enjoy your stay.

Guest suite in North Fork

A bright yellow door with a window covered by blinds is framed by gray shingles. Two exterior lamps are mounted on either side, and a small porch area features a decorative mat in front of the door.

4.91 out of 5 average rating, 286 reviews

Beachy En Suite /Gateway to The North Fork

Adorable,quiet,clean, w private entrance, private bedroom and bathroom,breakfast nook and patio.We are located in a beach front town dubbed“Gateway to the North Fork”.Walking/driving directions to local beaches,15minute walk to our community beach,Wildwood StPk(.6mi away).Niks deli nearby.Minutes by car to wineries,breweries,farm stands,EastWind,TangerOutlets15min away,35min to Hamptons,Greenport!Hosts live in adjoining house.NoTV but Wifi is good so bring your device for entertainment.

4.98 out of 5 average rating, 167 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 North Fork

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.

4.97 out of 5 average rating, 181 reviews

A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

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.

4.96 out of 5 average rating, 104 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.

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.

4.95 out of 5 average rating, 151 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.

A modern kitchen is showcased, featuring a large center island with four wooden bar stools. Stainless steel appliances and white cabinetry are complemented by granite countertops. Natural light filters in through a window above the sink, illuminating the inviting space.

4.94 out of 5 average rating, 143 reviews

Modern Farmhouse Retreat North Fork Wine Country

Escape to this modern farmhouse retreat in North Fork Wine Country. Enjoy a luxurious stay with a fully stocked kitchen, cozy fireplace, Spacious bedrooms, and spa-inspired bathrooms. Relax in peaceful surroundings close to farms, beaches, pumpkin & apple picking, Tanger Outlets, Splish Splash Water Park, and top wineries. Outdoor dining, private fire pit, scenic views, and nearby hiking trails make it perfect for families, couples, or friends.

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.

4.99 out of 5 average rating, 149 reviews

Luxury Hamptons Home with Heated Saltwater Pool

Get away from it all in this meticulously renovated Westhampton Beach home. Pull up to the cottage in the heart of Westhampton Beach, a place that delivers all the Hamptons have to offer, all while being within a two hour drive of NYC. No detail was overlooked in the renovation of this cottage… the beauty is only matched by the comfort and function. With the open floor plan, sunny kitchen, furnished open air patio, you won’t want to leave.

4.93 out of 5 average rating, 120 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 Rocky Point

Luxury modern farmhouse with heated pool & hot tub

*pool closes end of October This beautiful modern farmhouse is located on a one-acre lot and features a custom designed open-concept living space with vaulted ceilings that opens directly into a pool area. Hidden behind a bookshelf, you'll find a gorgeous game room with a piano and a pool table that can be easily converted into a ping pong table or working space. Please note that we do not allow weddings and events at this time.

Popular amenities for outdoor seating rentals in Baiting Hollow

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A grassy backyard area features a circular arrangement of four wooden Adirondack chairs surrounding a fire pit. In the background, a saltwater heated pool is visible, framed by lush trees and shrubs, creating a serene outdoor space.

4.94 out of 5 average rating, 32 reviews

Designer Home w/ Heated, Salt-Water Pool

4.97 out of 5 average rating, 34 reviews

The exterior of the cottage is surrounded by lush greenery, with a pathway leading to the entrance. A chimney stands atop the home, complemented by natural wood siding. A small patio area can be seen, nestled among tall trees, providing a tranquil spot for relaxation.

Home in Wading River

Cottage by the Sound

A dining area features a wooden table surrounded by four chairs, with natural light streaming through large windows. The view includes water and a serene landscape. A cozy living space is visible in the background, showcasing a green couch and a light rug.

4.98 out of 5 average rating, 57 reviews

Amazing river views, dock, close to great places!

4.89 out of 5 average rating, 111 reviews

A living room is highlighted by a cozy sofa draped with a light throw. A glass coffee table sits atop a soft rug. A fireplace is set within a white mantel, complemented by plants and framed art that add a touch of character.

Home in Bellport

The Stella ~ Bellport Beach ~ Monthly Winter Rates

A charming cottage is showcased surrounded by lush greenery, with a wooden deck extending from the front. The entrance is framed by a stone pathway leading to the house number visible in the foreground. Sunlight filters through the trees, creating a serene ambiance.

5 out of 5 average rating, 8 reviews

Cozy Beach Cottage

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.

4.98 out of 5 average rating, 182 reviews

Secluded Farmhouse - Studio Apartment Style Unit

4.99 out of 5 average rating, 140 reviews

A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.

Home in Milford

The ARLO - Walk to Brewery & Restaurants

A spacious living area is illuminated by natural light from large windows. A comfortable sofa and armchair are arranged around a low coffee table. A dining table with six chairs sits adjacent, while the kitchen is visible in the background. A staircase leads to the upper floor.

4.94 out of 5 average rating, 144 reviews

Modern 5BR Getaway • Close to Beaches & Wineries

Apartment rentals with outdoor seating

4.95 out of 5 average rating, 188 reviews

A spacious studio layout includes a cozy queen bed adorned with a geometric quilt. Nearby, a comfortable seating area features a patterned sofa and a green chair. Natural light flows through large windows adorned with bamboo shades, illuminating the warm wood floor.

Flat in Milford

The Boathouse, private downtown Harborside suite

4.98 out of 5 average rating, 189 reviews

An outdoor seating area is set up with wicker chairs surrounding a gas fire pit, glowing warmly in the evening light. A well-maintained green lawn and white privacy fence create a serene backdrop, with soft string lights enhancing the inviting atmosphere.

Flat in Islip Terrace

Near all 1 BR - Full Kitchen, Backyard & Fire Pit!

Flat in Port Jefferson Station

A dining area features a patterned tablecloth covering a wooden table, set for four with placemats. Natural light enters through large windows, illuminating a comfortable living room area with a sofa and side table. A decorative piece sits at the center of the table.

4.94 out of 5 average rating, 197 reviews

All Private Bright Spacious Close to All

4.98 out of 5 average rating, 117 reviews

A cozy living room features a spacious blue couch adorned with yellow accent pillows. A wooden coffee table is positioned in front, with colorful artwork hanging on the walls. A large flatscreen TV is mounted for entertainment, enhancing the comfort of the space.

Flat in Westville

Retreat in New Haven by Stephanie and Damian

4.95 out of 5 average rating, 180 reviews

A private kitchenette is displayed, featuring a wooden countertop, stainless steel refrigerator, and coffee maker. A small dining area with two wooden chairs and a round table is shown. Cozy seating is provided by a sofa adorned with decorative pillows. A doorway leads to the bathroom.

Flat in Sag Harbor

Sag Harbor / Noyack Pad - private STUDIO apartment

4.98 out of 5 average rating, 130 reviews

A sandy path leads through beach grass, flanked by wooden fencing, toward a tranquil ocean beyond. Clear blue skies complement the scene, where gentle waves are visible on the horizon.

Flat in The Hamptons

Walk to Bay and Ocean-Newly Renovated

4.98 out of 5 average rating, 129 reviews

Flat in Milford

The Pond Mill Retreat w/ 2 Bdrms & Pool

4.88 out of 5 average rating, 129 reviews

A gray couch adorned with teal pillows is positioned in the living room. A modern table set for dining and a serene beach scene artwork are displayed on the wall, while natural light flows in through a large window with a roller shade.

Flat in Medford

Home away from Home!

Apartment rentals with outdoor seating

4.81 out of 5 average rating, 78 reviews

Two individuals are seen enjoying a swim in a calm body of water, with sunlight reflecting off the surface. Lush greenery is visible in the background, creating a serene natural setting.

Apartment in Mount Sinai

1856 Trading House w/ walk to water

A living area features shiplap walls and ample natural light from large windows. A dark sectional sofa is positioned next to a glass coffee table with a small plant. An open kitchen area is visible, along with access to a screened porch through sliding doors.

4.87 out of 5 average rating, 126 reviews

Beautiful condo on Long Islands Northfork

An inviting living space features a light-colored wooden floor and white paneled walls. A cozy couch and soft ottoman complement a TV mounted on the wall. A dining table with chairs is positioned next to a window, allowing natural light to brighten the room.

Apartment in Ocean Bay Park

4.43 out of 5 average rating, 51 reviews

1BR Apt. in Ocean Bay Park with rooftop deck

4.84 out of 5 average rating, 143 reviews

A well-appointed bedroom features a spacious bed with decorative pillows, complemented by a cozy armchair with a vibrant red cushion. Natural light fills the room through large windows adorned with blinds, while an elegant painting adorns the wall above the bed.

Apartment in Fairfield

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr

A light-filled living area features a cozy neutral sofa, accompanied by a matching armchair. A decorative coffee table sits in the center, and a Smart TV is mounted on the wall. Sliders lead to a private waterfront deck with seating, enhancing the space's openness.

4.85 out of 5 average rating, 156 reviews

2 BR Waterfront Autumn Escape in Wine Country

Apartment in Old Saybrook

A cozy living area is furnished with a beige sofa, a round wooden coffee table, and stylish light blue armchairs. A large window allows natural light to fill the space. Potted plants add a touch of greenery, creating a relaxed atmosphere.

4.91 out of 5 average rating, 91 reviews

Seashore getaway - CT shoreline

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.

4.89 out of 5 average rating, 171 reviews

Beautiful Waterview Condo on the North Fork of LI

Two blue Adirondack chairs are positioned on a manicured lawn, facing a vibrant sunset over the ocean. The sky displays pink and orange hues as the sun sets on the horizon, creating a serene outdoor setting.