Apartment holiday rentals in Sag Harbor

A classic two-story house with a wooden exterior is framed by neatly trimmed greenery. The front porch features a white gate, inviting guests. Views of the water and trees are visible in the background, suggesting a serene location.

4.9 out of 5 average rating, 167 reviews

Whaling Captain Pierson's Apartment TOO

Whaling Captain Pierson's Apartment TOO is at a waterfront property. An apartment in one of the contributing homes which define Sag Harbor as a historic village. The house is a 7 minutes’ walk from the center of historic Sag Harbor Village. It is the only house and apartment offering a vast, picturesque, panoramic view of beautiful Sag Harbor Cove from Main Street as well as spectacular sunsets. (See my other listings of Whaling Captain Pierson's Apartment and Whaling Captain Pierson's Cottage)

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.

Apartment in Center Moriches

An open studio space features a spacious bed with a light duvet and decorative pillows. A leather couch complements the area, while large windows provide natural light, framed by white blinds. A bedside table and warm lighting create a cozy ambiance.

4.83 out of 5 average rating, 103 reviews

Quiet and comfy studio near the Hamptons

*If you have good prior reviews book our place and receive an offer within 24hrs! A well equipped cozy studio only 20 minutes from the Hamptons and 10 minutes away from LIRR train station to go into NYC (free parking at the train station!) This studio has a small kitchenette to warm up meals, a full size fridge, we include some snacks for those late night cravings. A queen size bed, a separate desk and chair to study or work, a couch, smart TV, and a peaceful environment to relax and unwind.

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, 198 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!

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, 412 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, 174 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, 225 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

Apartment 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 .

A private entrance features a white door set against a backdrop of textured wooden siding. Colorful purple irises bloom along the stone pathway, complemented by lush greenery, contributing to the inviting exterior of the studio apartment.

4.88 out of 5 average rating, 143 reviews

Southampton Village Studio

Location, Location, Location!!!! New renovated stand along Studio Apartment in the heart of Southampton Village. Private with lots of light, Cable TV and living room area. Located in wonderful Southampton Village location, only 1 mile to village shops and 2 miles Coopers Beach. Wi-Fi

Popular amenities for Sag Harbor apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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, 57 reviews

The Crow's Nest

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 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, 77 reviews

Sunny and Spacious 1BR Apartment

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 bright and airy studio space features large glass doors opening to a private patio with views of the dunes and ocean. A seating area with a sofa and coffee table complements the open layout, alongside a dining table and a spacious bed.

4.91 out of 5 average rating, 23 reviews

Oceanfront Corner Studio Bungalow on the beach

A secluded outdoor space features a clean, rectangular pool surrounded by a manicured lawn. Lounge chairs are positioned near the pool, offering a relaxing atmosphere. Trees provide shade, enhancing the serene environment with a wooden fence enclosing the area.

5 out of 5 average rating, 8 reviews

Casa Greenport 1st Floor

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!

Private apartment rentals

The exterior of a meticulously restored Victorian house is showcased, featuring a light grey façade with white trim and a welcoming front porch. A decorative railing borders the yard, which includes neatly maintained landscaping, and the entrance is highlighted by a brown front door.

4.99 out of 5 average rating, 73 reviews

Victorian Pearl

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 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.

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

5 out of 5 average rating, 7 reviews

Greenport Condo with Stunning Views & Beach Access

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 charming Victorian home features a blue exterior with white accents and a welcoming porch. Lush greenery surrounds the entrance, enhancing the inviting atmosphere. The property includes a second-story balcony, providing outdoor space to enjoy the surrounding neighborhood.

4.93 out of 5 average rating, 59 reviews

Lovely 1st floor of farmhouse, wineries/downtown

A panoramic view of the living area and kitchen is captured, showcasing a cozy couch with colorful pillows. A TV is mounted on the wall opposite, while a small table is arranged with greenery. Light enters through the windows, illuminating the neutral tones of the space.

5 out of 5 average rating, 7 reviews

Cute Hampton's Summer Apartment

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.

4.5 out of 5 average rating, 10 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, 81 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, 101 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.

4.75 out of 5 average rating, 4 reviews

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.

4.89 out of 5 average rating, 28 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.

5 out of 5 average rating, 3 reviews

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.