Apartment holiday rentals in Sag Harbor

A charming view is displayed through a large window, overlooking a green lawn that leads to a serene waterway. A decorative piece resembling a swan rests on a small table, casting a soft shadow as sunlight streams in.

4.93 out of 5 average rating, 166 reviews

Whaling Captain Pierson's Cottage

Whaling Captain Pierson's Cottage is at a waterfront property. A unique environmental experience, nestled in nature but only a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only cottage offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets and a private low-tide beach. (See my reviews from my other listings entitled, "Whaling Captain Pierson's Apartment" and "Whaling Captain Pierson's Apartment TOO".)

A charming two-story house is nestled among lush greenery, with large windows reflecting sunlight. The wooden exterior features shingle siding, and a gentle slope of grass leads up to the entrance. Surrounding trees create a serene, private atmosphere.

4.96 out of 5 average rating, 163 reviews

Hamptons Hills Escape

Located in a quiet and safe neighborhood tucked into the woods of Sag Harbor, yet just a 10-minute drive from Sag Harbor town. Down the road is "Morton's Wildlife Refuge" with a beautiful walk to a beach and where birds eat seed directly from your hand. The lovely Long Beach is 5 minutes away - day passes are available. You only have one entrance/exit to deal with, the white door at the top of the wooden stairs that are pictured. Perfect for a couple looking to cook, relax, and spin records.

A cozy living area is shown with two comfortable sofas and a coffee table. Natural light enters through two windows adorned with bamboo shades. A flat-screen television is mounted on the wall, and a decorative rug adds warmth to the wooden flooring.

4.98 out of 5 average rating, 194 reviews

Updated apartment in historic village home

Quiet updated apartment close to Main St, boats and beaches. This second floor apartment has a private entrance and allows use of the front yard. Our home was built in 1880 but has just been renovated for a modern beach bungalow feel. The location is the perfect balance of a quiet neighborhood and close proximity to Marine Park, shops, restaurants, the Hampton Jitney and nightlife. The center of main street is less than a quarter mile from the apartment (4 minutes on foot). Walk to all!

4.94 out of 5 average rating, 138 reviews

A serene beach scene captures a golden sunset reflecting on calm waters. The sandy shore leads to gentle ripples, while distant land silhouettes frame the horizon. A tranquil ambiance is created as the sun descends, providing a peaceful setting for evening strolls.

Flat in South End

Bright, Southold Studio Apt near beach & town

Pied a terre on the North Fork, in the heart of Southold village. Gorgeous bay beach 5 minute walk, as are farmstands, supermarket, Historic Southold Village with quaint shops, Hampton Jitney & LIRR. Lots of light, new contemporary space featuring full bathroom with bathtub. Perfect for one, suitable for a couple for weekend getaway. Small kitchenette perfect for simple food prep, morning coffee/tea. Chickens on property, fresh pastured eggs in your kitchenette upon arrival!

A cozy living area features a comfortable gray sofa adorned with patterned pillows. A light-colored side table and an illuminated lamp create a soft glow. A decorative coffee table sits in front, accompanied by a potted plant in the corner, adding a touch of greenery.

4.92 out of 5 average rating, 119 reviews

Private 1st flr apt w/ patio 3 blocks from beach

We are centrally located in a quiet neighborhood within blocks from the heart of Greenport Village, Peconic Bay Beach, LIRR/Jitney, restaurants, shopping, Mitchell Park, and more! Explore local farms, wineries, breweries and all the North Fork has to offer. Beautifully furnished, ground floor apt with private entrance & patio area comfortably sleeps four, features a queen Tempur-Pedic mattress & convertible couch. Friendly, housetrained pets are welcome for an additional charge.

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, 411 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.

A bright living area features two windows, allowing natural light to fill the space. A white sofa and an accent chair are positioned around a small coffee table. Artwork adorns the walls, complementing the light color palette. A dining table with two chairs is visible in the corner.

4.89 out of 5 average rating, 172 reviews

Sag Harbor Village Oasis

Bright and spacious second floor apartment in historic Sag Harbor Village. 10 minute walk to historic Sag Harbor Village Main Street. Five minute walk to Bay beach. Super comfy king bed. Fully self contained with private entrance and hallway. Parking on street close to entrance. Kitchen with stovetop, refrigerator, sink, coffee and tea kettle. No pets - owner is allergic. No infants/children.

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.

4.98 out of 5 average rating, 130 reviews

Walk to Bay and Ocean-Newly Renovated

Newly renovated! Walking distance to beautiful bays , ocean beaches, restaurants and bars. Perfect Hamptons vacation getaway. Wine Country and Montauk are great day trips from this centrally located spot. Easily access Hampton Bays with public transportation via LIRR or Hampton Jitney, than a 3-5 minute Uber to apartment. Monthly stays will have cleaning service provided every two weeks.

A wide sandy beach stretches towards the horizon, where soft waves gently lap at the shore. Tall lifeguard stands are positioned along the beach, with a few distant figures walking. The sky features a gradient of muted colors as the sun sets, creating a serene atmosphere.

4.95 out of 5 average rating, 223 reviews

Sunny Southampton Studio

Newly renovated sun drenched, spacious studio in Southampton. Five minute drive to Main Street, while still in close proximity to some of the most beautiful beaches. Queen size bed and queen size pull out couch. Full kitchen with new appliances and full bathroom. BEACH PASS for Coopers beach is available upon advanced request—please let me know the day before you arrive

Flat in Shelter Island Heights

A round wooden dining table is surrounded by four metal chairs. Natural light enters through two large windows, with framed black-and-white photographs arranged on the wall beside them. A decorative centerpiece is placed on the table, offering a rustic touch to the space.

4.9 out of 5 average rating, 259 reviews

Squire Chase House

Wide open loft like space in the heart of the Heights walking distance to North ferry and Marie Eiffel market Many antiques including 1930s leather club chairs and a wonderful 1850 Swedish gustavian sofa in the living room many original pieces of art work Note :the bath tub in the master bedroom is for decoration only Shelter Island license B Zone

A bright bedroom features white shiplap walls and large windows allowing natural light. A spacious bed is adorned with a textured white blanket and colorful decorative pillows. A vibrant area rug adds warmth, alongside a small table, a cozy armchair, and decorative plants.

4.83 out of 5 average rating, 185 reviews

Quiet Neighborhood and only steps to Town

Walk the 5 min into town with restaurants and bars, shops and cafes or enjoy the quiet neighbourhood and take a stroll down the block to watch the sailboats cruise into Sterling Harbor. This sunny apartment is situated on the second floor of a 1860's house on one of Greenport's prettiest streets. Its the true couples getaway!

A bright living area is depicted, featuring a sleek sofa, a wooden coffee table, and a round dining table surrounded by red chairs. The space incorporates a large potted plant, and light streams through a nearby window, illuminating the whitewashed wood floors.

4.97 out of 5 average rating, 129 reviews

Renovated Guest Cottage close to E.Hampton Village

This modern beach guesthouse has white washed wood floors, all new stainless steel appliances , central air, and very conveniently located . We are a short walk to East Hampton Village and 1.9 miles to the nearest beach.There is a private back patio with a cedar outdoor shower and sitting area in a serene setting .

Popular amenities for Sag Harbor apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

Two bright orange chairs are positioned beside a small wooden table adorned with a potted plant and books. A cozy atmosphere is created in a well-lit space featuring light-colored flooring and natural light from the nearby window.

5 out of 5 average rating, 72 reviews

Hampton Studio

A cozy living area features wood-paneled walls and a neutral sofa positioned near a lamp and a chair. Natural light floods through the windows, illuminating a patterned rug on the hardwood floor. A television is mounted on the wall opposite the entrance.

4.92 out of 5 average rating, 12 reviews

Sugarloaf Annex

A comfortable seating area is visible, featuring a soft gray sofa adorned with pillows. A round, white table is placed in front. Light-colored wood doors with glass panels lead to another room, enhancing the sense of openness within the space.

4.84 out of 5 average rating, 31 reviews

2BR Hampton's Serenity Getaway w/Kayaks and BBQ

The exterior of the two-story apartment is showcased, featuring grey siding and multiple windows with white trim. A defined driveway leads to the building, bordered by manicured greenery. Sunlight casts soft shadows across the landscape, enhancing the inviting atmosphere.

5 out of 5 average rating, 14 reviews

Beachside Bliss

The exterior of a spacious two-story home is shown, featuring a light beige façade and large windows. A set of white steps leads to the front door, flanked by neatly maintained shrubs. The property includes a two-car garage and a paved driveway.

5 out of 5 average rating, 16 reviews

The Hamptons

A serene sleeping area features a spacious bed dressed in crisp white linens and accented by a dark throw pillow. Framed artwork adorns the walls, while stylish side tables complement the modern aesthetic. Floor-to-ceiling curtains in a neutral tone add a touch of elegance.

4.85 out of 5 average rating, 86 reviews

Private Newly built Modern East Hampton Apartment!

A cozy living area features a grey sofa adorned with decorative cushions, along with a white accent chair. Natural light floods in from two large windows, casting a warm glow on the wooden floor. An American flag decorates the wall, adding character to the space.

4.97 out of 5 average rating, 100 reviews

Stunning Garage Apartment!

A relaxed living area features a comfortable gray sofa positioned next to a round wooden dining table. A large mirror reflects light from the adjacent window, while a decorative lamp provides warm illumination. A flat-screen TV and wooden cabinet are also visible in the space.

4.97 out of 5 average rating, 39 reviews

Updated Carriage House Apartment

Private apartment rentals

A bright sleeping area features a spacious bed with white linens and a blue accent pillow. Natural wood elements are present, including a light-colored bed frame and a woven rug. A soft glow is provided by a pendant light, alongside a piece of coastal artwork on the wall.

5 out of 5 average rating, 10 reviews

Beachy and cozy private room.

A light-filled living room features a comfortable gray sofa adorned with decorative cushions. Two stylish chairs, with soft white covers, are positioned beside a coffee table that includes decorative books. Warm lamps create a cozy atmosphere, while a patterned rug adds texture beneath.

4.98 out of 5 average rating, 56 reviews

The Crow's Nest

A warm wood-paneled interior features a cozy bed adorned with a white quilt and decorative pillows. A small yellow bench sits at the foot of the bed. A bathroom entrance is visible in the background, and a landscape painting hangs above a nightstand with a lamp.

5 out of 5 average rating, 26 reviews

The Vineyard Studio of the Hamptons.

A spacious bedroom is featured with a large bed, flanked by two nightstands. A cozy couch offers additional seating, and a light fixture adds warmth to the space. Soft curtains frame a window, allowing natural light to fill the room, complemented by a decorative area rug.

5 out of 5 average rating, 22 reviews

Springs Plaza

The kitchen features light grey cabinets with white countertops, complemented by stainless steel appliances. A small dining table with two stools is positioned near the window, allowing natural light to brighten the space. Hardwood flooring provides a warm touch to the modern design.

4.96 out of 5 average rating, 23 reviews

Charming 2 Bedroom Apt in Dwntwn Greenport

A comfortable living area is furnished with a large gray sectional sofa and an armchair. A flat-screen TV is mounted on the wall opposite. Natural light floods through large windows, creating a relaxed atmosphere. A small table sits on the light-colored area rug, complementing the wooden floor.

4.83 out of 5 average rating, 76 reviews

Sunny and Spacious 1BR Apartment

A spacious room features a large bed with a green accent blanket and a simple headboard. Natural light flows in through a large window, offering a view of greenery outside. A light wood dresser and minimalist decor complete the serene atmosphere.

4.9 out of 5 average rating, 10 reviews

Stay in Westhampton for Less

5 out of 5 average rating, 3 reviews

Greenport Condo with Stunning Views & Beach Access

Apartment rentals with a hot tub

An open-plan living area features a light-colored floor and walls, with a large sectional couch in a soft gray hue arranged around a simple coffee table. A dining table with white chairs is positioned nearby. Natural light illuminates the space, creating a bright atmosphere.

4.67 out of 5 average rating, 3 reviews

Elegant 2BR Beach Condo

A serene waterfront view showcases a private deck adorned with lush greenery and vibrant flowers. A saltwater hot tub and lounge area invite relaxation, while the expansive water stretches into the distance. Comfortable seating arrangements enhance the tranquil outdoor environment.

4.94 out of 5 average rating, 80 reviews

Hamptons Waterfront Escape/ Hot Tub/ Resort Style

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.

4.96 out of 5 average rating, 100 reviews

Swimming pool w/Hot tub Fire Pit Coffee Bar

A spacious living area is shown with light-colored wooden flooring. Two comfortable leather sofas face a coffee table, complementing a dining table with black chairs. A well-equipped kitchen is partially visible in the background, illuminated by natural light from multiple windows.

Resort Living in Amagansett

The living area is seen featuring a light-colored sofa and armchair with soft textures. A small table holds decorative items and a woven basket. The kitchenette is visible, equipped with modern appliances and a window that allows natural light to brighten the space.

4.88 out of 5 average rating, 26 reviews

Pet-Friendly Apt w/ Hot Tub Near the Hamptons!

A bright living area features a green sofa and comfortable chairs, with natural light flooding in through sliding glass doors that lead to a balcony. A simple coffee table sits atop a woven rug, while a kitchen bar adds functional space to the open layout.

2 Bed 2 Bath Oceanfront Condo

A modern living area features a spacious sectional sofa, a dining table, and a large television mounted on the wall. Natural light is streamed through sliding glass doors leading to a patio. A well-equipped kitchen is visible, showcasing a stylish countertop and sink.

2 Bedroom Condo at the Hermitage!

A spacious living area features two light blue sofas and a textured area rug, complemented by a wooden coffee table. Natural light enters through sliding glass doors, which lead to a balcony. A wall-mounted TV and an accent chair add functionality and comfort to the space.