Apartment holiday rentals in Greenport West

4.98 out of 5 average rating, 256 reviews

A cozy living space features a light-colored sofa with yellow accents, positioned beside a small round table. A striped area rug adds texture to the hardwood floor. Bright natural light enters through nearby windows, illuminating the space and connecting to the kitchen and bathroom beyond.

Apartment in Dwight

Bright 1 BR Apt Steps From Yale

Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

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, 197 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.

Apartment 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.

An open living area features a comfortable gray sofa facing a flat-screen TV. A black coffee table sits on a textured rug, while a wooden dining table with chairs is positioned nearby. Sunlight filters through the blinds of the dual doors leading to the outside.

4.93 out of 5 average rating, 123 reviews

Junior 1-BR in the heart of Greenport Village

Beautiful junior one bedroom in the heart of Greenport Village. Located in the historical district, our basement apartment is walking distance (2-Blocks) to downtown Greenport. Perfect for a couples weekend, girls trip, or for a small family. Our apartment includes one queen bed and a twin day bed with trundle underneath. (Sleeps 4 total) TV with streaming service and WiFi are included. W/D are available upon request.

A bright and airy great room combines kitchen, dining, and living areas. Light wood cabinetry and stainless steel appliances complement the open layout. Soft white sofas with navy pillows are arranged around a wooden coffee table, and a round mirror enhances the natural light from multiple windows.

4.96 out of 5 average rating, 166 reviews

Upscale Newly Constructed Apartment

Upscale 2- story building offers 3 bedrooms, 2 baths spacious apartment in the heart of Greenport. A vaulted ceiling in the great room (kitchen, dining & living room) with large windows and hardwood floors with plenty of natural light. Utilities included. CAC, Laundry. Less than a mile to a public beach, public transportation, restaurants, shops and Mitchell park. Off street parking for 2-3 cars.

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, 173 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 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

The main bedroom features a spacious bed with a white comforter and dark accent pillows. Sunlight filters through sheer white curtains covering French doors, leading to the outdoors. Bright wooden floors add warmth, while a ceiling fan offers comfort.

4.97 out of 5 average rating, 116 reviews

Lovely 2-bedroom apartment in a historic home

Restored apartment in a Victorian home, centrally located in the Village of Greenport. Short, few minutes walk to restaurants, shops, cafes in town. Also, conveniently located (10 minute walk) to the Hampton Jitney bus stop, LI Railroad and Shelter Island Ferry as well as local beaches. Enjoy the charm of a historic home, with all the convenience of modern amenities!

Superhost

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.

Apartment in Shelter Island Heights

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 spacious bed is adorned with neatly arranged, textured pillows in varying patterns, including striped and solid colors. Bright white linens provide a fresh contrast against the dark wooden headboard.

4.95 out of 5 average rating, 262 reviews

Greenport Village View - Walk Downtown 2BR/1BA

Located in the heart of Greenport Village with easy walking access to restaurants, shops, Greenport Brewery, Kontakasta Winery, and much much more! Originally from Greenport, we look forward to hosting you and sharing our local favorites to make your stay memorable. Please note this rental may not suitable for small children due to the staircase.

Popular amenities for Greenport West apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly 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 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

A light-filled living area features a comfortable sectional sofa with decorative pillows. A coffee table rests on a textured area rug, accompanied by framed art on the white walls. Natural light enters through a window overlooking greenery, accentuating a serene environment.

4.92 out of 5 average rating, 51 reviews

Spacious One Bedroom Apartment, Close to Beaches

4.9 out of 5 average rating, 212 reviews

The historic Ludington House features a grand white facade with black shutters and a central entrance. A large porch with a decorative railing enhances the welcoming appearance. Lush greenery and landscaped flower beds flank the pathway leading to the front door, creating an inviting entry.

Apartment in Old Lyme

Private apartment in historic Old Lyme mansion

The sleeping area features a plush bed with white bedding and two neatly arranged pillows. Warm light from the wall-mounted lamps illuminates the space, while green foliage is visible through the large windows on either side, creating a soothing atmosphere.

4.98 out of 5 average rating, 43 reviews

The Hideaway | Clearwater Beach

5 out of 5 average rating, 40 reviews

A large two-story house features a dark exterior with stone accents and multiple gabled roofs. Large windows allow ample natural light to enter, while a wooden front door adds a welcoming touch. Lush greenery surrounds the property, enhancing its natural setting.

Apartment in Branford

Stedley Creek

5 out of 5 average rating, 6 reviews

Greenport Condo with Stunning Views & Beach Access

4.98 out of 5 average rating, 125 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.

Apartment in Westville

Retreat in New Haven by Stephanie and Damian

Private apartment rentals

The charming two-story building features a light-colored exterior with shingle accents. A covered porch spans the front, supported by tall white columns. Large windows invite natural light, while blooming trees enhance the inviting street view.

4.98 out of 5 average rating, 80 reviews

Newly Renovated 2-BR Apartment

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

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

4.99 out of 5 average rating, 84 reviews

A light and airy living area features a comfortable cream-colored sofa, a dark upholstered chair, and a modern television stand. A large area rug covers the floor, while a potted plant adds a touch of greenery. Natural light filters through a nearby window.

Apartment in Clinton

Cozy Shoreline Getaway

4.97 out of 5 average rating, 69 reviews

A cozy bedroom area features a spacious bed with soft linens and decorative pillows. A small white side table and a round light fixture are present. A comfortable white sofa and a modern black chair are arranged in the relaxation area, alongside a neutral patterned rug.

Apartment in Edgewood

Beautiful Cozy Apt/ Soaking Tub & Serene Vibes

Superhost

4.92 out of 5 average rating, 26 reviews

Peaceful getaway in the Hamptons

Apartment in Prospect Hill

A well-lit bedroom features a spacious bed, accentuated by a floral wallpaper backdrop. A large skylight and a window allow natural light to fill the room. A woven bench sits at the foot of the bed, complemented by a green plant near the window.

4.98 out of 5 average rating, 175 reviews

Skylight: Cozy 2 BR, Close to Yale & Downtown NHV

A cozy living area features a green patterned accent wall and a comfortable sofa. A television is positioned on a white media stand, while a rustic dining table and chairs are present. A bright red fridge adds a pop of color, and a lofted sleeping area is accessed by a blue-painted staircase.

4.94 out of 5 average rating, 65 reviews

Sunny 1 bedroom Guest Suite w/private entrance

Apartment rentals with a hot tub

The spacious bedroom features large windows allowing natural light to fill the room. A modern ceiling fan is installed, and a wall-mounted television is positioned above a sleek electric fireplace. The comfortable bed is adorned with a crisp white coverlet.

Apartment in New Haven

West River Gem.

Superhost

A spacious sleeping area is highlighted by a large bed featuring a decorative headboard with an intricate blue pattern. Two bedside tables hold modern lamps, and a crib is positioned nearby, offering a family-friendly environment.

Apartment in Wooster Square

4.77 out of 5 average rating, 150 reviews

Luxury Penthouse Minutes to Yale

A minimalistic studio apartment showcases a spacious bed with a dark coverlet. A small dining area with high chairs is positioned beside a large window. Exposed wooden beams and neutral-toned walls create a contemporary feel, while a decorative plant adds a touch of greenery.

Apartment in Dwight

4.16 out of 5 average rating, 19 reviews

Cellar Studio Apartment

A light-colored seating area features a modern, compact couch positioned against a white wall. Above the couch, two decorative wall art pieces showcase abstract patterns in natural tones. Light hardwood flooring extends throughout the space, contributing to an open and clean aesthetic.

Apartment in East Shore

Near Tweed, Yale & The Estate, Mins to Downtown

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

Apartment in Shirley

4.5 out of 5 average rating, 10 reviews

A 1 BR home away from home to relax and unwind.

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.