Vacation rentals in Port Chester

4.91 out of 5 average rating, 125 reviews

A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.

Home in Rye

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

Apartment in White Plains

A modern bedroom features a four-poster bed with plush bedding and a decorative bolster pillow. Natural light floods the room through large windows, framed by dark curtains. A contemporary TV is mounted on the wall, and a wooden dresser with a wine bottle is positioned nearby.

5 out of 5 average rating, 9 reviews

Designer 1BR | Luxe Amenities, Gym, Parking

Welcome to your luxury White Plains escape, a modern one-bedroom retreat with all the comforts of home and the amenities of a five-star resort. • Deep-cleaned before every stay • Rooftop green, coworking lounge, and private pods • Game room with virtual golf, pinball, and shuffleboard • Resort-style pool deck with grills, and fireside lounge (Closed for the season!) • State-of-the-art fitness center with on-demand classes • Steps from restaurants & shops; easy walk to Metro-North to NYC (45min)

4.91 out of 5 average rating, 45 reviews

A well-lit bedroom is showcased, featuring a spacious bed with plush pillows. Tasteful art pieces are displayed on the wall, and a mirror stands beside the bed. A built-in shelving unit provides storage, while a door leads to the adjacent lounge area.

Guest suite in Cos Cob

Cozy Guest Suite in Greenwich, 1mi from train

A light-filled studio with private entrance in a newly renovated home. Nestled on a very quiet street, it offers a queen size bed with private bathroom and lounge space (sofa bed) . The space small kitchen amenities include a refrigerator, coffee machine, kettle and microwave, Wi-Fi and private bathroom with shower are additional features. Other things to note As we are a young family looking for total quiet during your stay? We may not be the best hosts for you. Otherwise, please reach out!

4.96 out of 5 average rating, 57 reviews

A cozy living room features a large flat-screen TV mounted on the wall, accompanied by a sleek entertainment unit. A comfortable couch is draped with a soft blanket, and an armchair is positioned nearby. Natural light enters through two windows, brightening the neutral decor.

Guesthouse in Mamaroneck

Spacious guest suite near water

Welcome to your perfect home away from home! Enjoy a spacious and newly renovated basement suite with windows and separate entrance in a private house, perfect for up to four guests. Ideal for couples, small families, or business travelers. This cozy retreat, combines privacy and comfort in a quiet neighborhood. Whether you’re here for a short trip or an extended stay, this apartment offers everything you need for a comfortable and relaxing experience. Book now and start planning your visit.

4.89 out of 5 average rating, 133 reviews

A private deck is displayed with wooden planks, featuring a sun lounger and a small table with two chairs. A large umbrella provides shade, while trees can be seen in the background, enhancing the outdoor experience.

Cabin in Greenwich

Overlook Cabin in downtown Greenwich CT

Last house on a private road, parking onsite if available, conveniently located walk to train station, Greenwich Avenue in Greenwich CT to the ferry, Sherman Park for beach access. Travel to New York City in 37 minutes with the Metro-North Express train. We are at one of the highest points on the Greenwich Coastline. You can hear the sounds of life: from church bells ringing, the train to NYC and Rt 95 traffic, NO SMOKING NO parties NO events Sorry NO PETS service animals always welcomed.

4.81 out of 5 average rating, 109 reviews

A white anchor, inscribed with 'BYRAM SHORE BOAT CLUB,' is positioned prominently in a landscaped area. It is surrounded by greenery and colorful blooming flowers, set against a backdrop of finely textured gravel.

Home in Byram

Greenwich abode Close to Just about Everything

2 - Bedroom apartment in a duplex. 4 - Minutes to Greenwich Avenue Shopping 6 - Minutes to Port Chester restaurants 8 - Minutes to Rye town and restaurants. 36 - minutes to NYC 1 - Twin Air Mattress, SERTA auto inflate, 15 inch raised { UPON REQUEST } 4 - Minutes Uber/Lyft drive to Greenwich and Port Chester Metro North Station Private and cozy retreat, steps away from one of Greenwich's Top Beaches - Byram Shore Beach Club.

4.96 out of 5 average rating, 302 reviews

A well-appointed kitchen features wooden cabinetry and modern appliances. A round dining table is set for two, complemented by a vibrant plant centerpiece. The space is illuminated with soft lighting, enhancing the inviting atmosphere while maintaining ample counter space.

Apartment in Harrison

Luxury Private Apartment - Walk to Train for NYC!

Luxury Large Private One Bedroom Apartment. With private walkway and entrance. Full Kitchen with New Appliances. King size Bed with Move Projector and Screen. Large couch with Desk in Living room. Updated Bathroom with Bathtub. Walking Distance to Harrison Train Station - Harrison Metro North Train Station access to New York City or Greenwich / Stamford CT. To Grand Central Station. Walking Access to local Parks.

4.94 out of 5 average rating, 78 reviews

An open living area features a comfortable gray sectional sofa beside a light area rug. The modern kitchen includes wooden cabinetry, stainless steel appliances, and a countertop with bar seating. A large TV is mounted on the wall, providing entertainment within the inviting space.

Townhouse in Byram

Quaint duplex + pvt yard. Walk to town & beach!

Located on a quiet street, our fully renovated duplex apartment in Greenwich boasts hardwood floors, a washer-dryer, heating, air conditioning, and a fabulous modern kitchen. The living room has a large screen 4k TV and an electric fireplace for you to enjoy. The private patio just off the kitchen allows you to relax outside whenever you like. Walk to restaurants, trains, parks & more!

4.95 out of 5 average rating, 100 reviews

A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.

Guesthouse in Greenwich

The Cottage in Greenwich

Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.

Apartment in Port Chester

A sleeping area features a spacious bed with light-colored bedding, accompanied by neatly folded towels. A wall adorned with greenery and string lights adds a cozy ambiance. A television is mounted nearby, with a framed picture featuring a car on the wall.

5 out of 5 average rating, 4 reviews

Downtown Port Chester near train walk to shops

Cozy, cutely decorated apartment just steps from the Port Chester train and vibrant downtown. Enjoy a full kitchen, fresh linens, and free high-speed Wi-Fi. Coin-operated washer/dryer available on premises. Perfect for work or play, this comfy space is ideal for solo travelers or couples looking to relax and explore. Book your stay today and feel right at home!

Apartment in Port Chester

A cozy living room features a large sectional sofa adorned with decorative pillows. A glass coffee table sits on a soft area rug, while a flat-screen TV is mounted on the wall. Two windows allow natural light to fill the space, enhancing its inviting atmosphere.

4.97 out of 5 average rating, 87 reviews

Sunny & Cozy Stay by Capitol Theatre/Downtown

Within walking distance of downtown Port Chester, Capitol Theatre, Metro North, and so much more; this 2 bedroom apartment with PRIVATE ENTRANCE provides a comfortable, inviting stay for those visiting the New York City/Metropolitan area. We are centrally located near the I-287, I-95, so commuting to and from the area is easy.

4.99 out of 5 average rating, 170 reviews

A compact kitchenette area features modern appliances including a microwave, coffee maker, and refrigerator. A small bar counter with two stools is positioned near the entrance. Light gray walls and natural wood flooring create a welcoming ambiance.

Home in West Side

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

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Popular amenities for Port Chester vacation rentals

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Other great vacation rentals in Port Chester

Private room in White Plains

A wall-mounted 43” smart TV is displayed above a modern wall fireplace featuring ambient lighting. A wooden desk with a chair is positioned adjacent to the fireplace. The room is painted in a neutral tone, with natural light streaming through a window with slats.

4.83 out of 5 average rating, 191 reviews

A cozy and comfortable bedroom

4.82 out of 5 average rating, 77 reviews

Private room in Bronx

Spacious Modern Room 2-C

4.71 out of 5 average rating, 113 reviews

The exterior of Hyatt House is displayed, featuring a three-story building with multiple windows surrounded by well-maintained grassy areas and trees. The entrance is marked by a stylish overhang, and soft outdoor lighting enhances the welcoming ambiance during twilight.

Hotel room in Purchase

Near Manhattanville Univ + Free Breakfast & Pool

A cozy room is equipped with a spacious bed and a soft armchair. A small ottoman sits at the foot of the bed. A desk and chair are positioned near a large window, which allows natural light to fill the space, complemented by light-colored curtains.

Private room in Port Chester

4.8 out of 5 average rating, 121 reviews

Great location, close to HPN and Capitol Theater.

Private room in Mamaroneck

A keyless entry system is displayed on a wooden door, featuring a circular keypad with numbers ranging from 0 to 9. A round door knob is positioned beneath the keypad, enhancing the contemporary and secure access method.

5 out of 5 average rating, 7 reviews

Private BR, near NYC, 5min walk to train

4.96 out of 5 average rating, 98 reviews

Private room in Elmsford

Quiet room in the heart of Westchester

Private room in Mamaroneck

4.79 out of 5 average rating, 19 reviews

Room near NYC