Vacation rentals in Port Chester

4.9 out of 5 average rating, 112 reviews

The spacious living area features large glass walls that provide serene views of the surrounding forest. A modern white sofa complements a wooden ceiling, while a quirky red chair adds a pop of color. Natural light floods the room, enhancing the warm wood tones throughout.

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 Downtown Stamford

A balcony is equipped with outdoor furniture, including two chairs and a small table. The scene is enhanced by a view of the city skyline during sunset, with soft, warm lighting reflecting off the buildings. Glasses are placed on the table.

4.96 out of 5 average rating, 200 reviews

Sugar Shack Studio | Downtown Skyline Views

Location! Studio apartment located in the heart of downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and a short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 10 minute walk. Washer and Dryer included in the building with credit card payment. This unique place has a style all its own!

4.92 out of 5 average rating, 119 reviews

A formal dining area is highlighted by a large table surrounded by light grey upholstered chairs. A rustic stone fireplace adds warmth to the space, while a large mirror reflects natural light. Soft curtains frame the window, creating an inviting ambiance.

Home in White Plains

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

4.99 out of 5 average rating, 142 reviews

A charming exterior view of a cottage is presented, framed by lush greenery and vibrant flower beds. Hydrangeas in varying shades of blue and green are prominent in the foreground, while the entrance is decorated with pink flowers and flanked by shrubs, enhancing the inviting setting.

Guesthouse in Rowayton

1BR full cottage, 1 min walk to private beach

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian and dog friendly town; you don't even need a car while here.

4.89 out of 5 average rating, 117 reviews

Cabin in Greenwich

Overlook Cabin in downtown Greenwich CT

Last house on a private road, two parking spaces 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.

4.91 out of 5 average rating, 518 reviews

A serene waterway flows gently through a leafy forest landscape. Sunlight dapples the water's surface, reflecting the surrounding greenery and smooth stones. Lush foliage frames the banks, creating a peaceful and natural environment suitable for relaxation and contemplation.

Guest suite in Cos Cob

Charming Greenwich studio, 0.2 miles from train

A charming and spacious "studio" with private entry/exit and very close proximity to Cos Cob train station in Greenwich. Opens to a private back yard. Small library, stone walls, small desk, private hall and bath, and room for 2 (or 3) make it ideal for a weekend getaway with easy access to NYC, Port Chester, Stamford, and New Haven. Five minute walk to Cos Cob village for bakeries, juice and coffee shops, and restaurants. Kid-friendly. Air mattress or crib available upon request.

4.84 out of 5 average rating, 158 reviews

The approach to the house features a stone pathway leading up to a front porch, flanked by neatly arranged flower planters. The well-maintained lawn provides an inviting green backdrop. Steps lead up to the entrance, with a decorative light fixture positioned along the pathway.

Home in Stamford

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

4.81 out of 5 average rating, 104 reviews

A spacious area is shown with several green picnic tables situated on a grassy surface, overlooking a sandy beach. Lush trees provide a backdrop, while visitors can be seen enjoying the beach. The sky features scattered clouds with bright blue hues.

Home in Greenwich

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, 297 reviews

The bathroom features a shower curtain displaying a skyline design, depicting tall buildings in shades of blue. A countertop with storage is visible, along with essential amenities, while light-colored walls and a clean aesthetic contribute to the overall 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.

Apartment in Port Chester

The bathroom features a clean and tidy layout with a bathtub and shower combination. A compact washer and dryer are located beside the bathtub. A sink with a mirror overhead and a toilet are also present, all set against a tiled floor.

4.96 out of 5 average rating, 76 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, 166 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 Stamford

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Port Chester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Port Chester

4.95 out of 5 average rating, 91 reviews

A private cottage entrance is framed by a sloped roof, featuring a large glass door complemented by a small window. Two modern chairs are positioned on the welcoming wooden deck, while a doormat adds a touch of practicality.

Guesthouse in Greenwich

The Cottage in Greenwich

PeterRating, 5 stars1 month ago

This unique recently built cottage is really a private bower in a shady maple forest. For the walker there is a sidewalk path down to the little township center only three-quarters of a mile's pleasant stroll. A large TV has its own useful networks and allows patrons to load their own subscribed streaming connections. There is a functional kitchenette. For those wishing a quiet, stress-free stay in a location convenient to a thriving, busy urban setting this is ideal. Only about 10 minutes drive to Westchester airport.

4.95 out of 5 average rating, 74 reviews

Townhouse in Greenwich

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

BarbaraRating, 5 stars3 weeks ago

Very comfortable, lovely furniture, great beds, adjustable temperature for each area. Well stocked kitchen with everything you need. The stairs are are narrow, maybe tricky for some guests with mobility issues. The outdoor spaces are fantastic and private. Safe area with lots to do. Highly recommend for family or small groups!

Apartment in Port Chester

Two coin-operated laundry machines are displayed side by side in a laundry area. Each machine features a sleek, white exterior with control panels that include digital displays and coin slots. The background shows utility connections and a trash bin.

5 out of 5 average rating, 4 reviews

Downtown Port Chester near train

KennyRating, 5 stars1 month ago

Priscila's home is sparkling clean and very convenient as it is near many restaurants.Priscila is very responsive to my queries and also very helpful too.

4.98 out of 5 average rating, 43 reviews

A well-maintained garden features lush green grass and a variety of trees and flowering plants, creating a vibrant natural setting. The surrounding property presents a charming two-story building, partially obscured by foliage, against a clear blue sky, enhancing the tranquil ambiance.

Guesthouse in Larchmont

Beautiful guesthouse - Larchmont

MichaelRating, 5 stars1 month ago

This recently renovated unit was exceptionally nice. Decorator touches, extremely clean. Drinks in the fridge, snacks, toiletries - basically any need met. Joanna was a great host, good communicator, friendly. The unit was spacious and highly functional. I would not hesitate to go back.

4.95 out of 5 average rating, 43 reviews

The outdoor deck offers a spacious area with wooden planks, accompanied by sun chairs arranged for relaxation. A stone fire pit sits in the foreground, while a barbecue grill is positioned nearby. Lush trees frame the background, creating a serene natural setting.

Home in Greenwich

Riverfront Cottage Retreat & Pool 35 mins from NYC

LucyRating, 5 stars4 weeks ago

Fabulous getaway, beautiful surroundings, hard to believe we were just a few minutes from highways and downtown and civilization! Responsive host, many amenities -- pool, bbq, outdoor dining, waterfall, river view, soaking tub, sun loungers, spacious kitchen, dreamy sofa.

5 out of 5 average rating, 15 reviews

A sliding closet door opens to reveal neatly organized shelves. Fresh, white towels are stacked, and a clothing rod is available for hanging items. The interior is painted to match the warm tones of the surrounding walls and features a hardwood floor.

Condo in Stamford

Comfortable, Beautiful Apartment-Close to Downtown

KarenRating, 5 stars1 week ago

I am new to the Stamford / Greenwich area and needed a place to stay while I looked for a permanent residence. I stayed at Juan's place for about 3.5 months. It was very convenient to Greenwich (where I work) and to downtown Stamford (restaurants and shops) and the Stamford train station, which has great express trains to NYC. It is also very close to a grocery store and several gyms (I chose Orange Theory, only a few blocks away). I chose Juan's place for the location and king size bed. The bed was very comfortable, the towels were great and the overall unit worked really well for myself and my husband - it has wifi and we connected to our Netflix & other apps thru the smart TV. It fits two people comfortably and has a pull out sofa for guests (my college-age children visited a few times). The kitchen has what you need, including a dishwasher. There is one permanent parking space available and several guest spots. Juan was very responsive and a great host. Highly recommend!

5 out of 5 average rating, 37 reviews

A spacious living area is illuminated by natural light coming through two windows. A small round dining table surrounded by four chairs is positioned near the center, while a cozy seating area with a couch and decorative plant can be seen in the background.

Guesthouse in Mamaroneck

Spacious guest suite near water

ElizaRating, 5 stars3 days ago

This place was perfect for our needs to get some rest for a night after a long flight into JFK. The drive from the airport was easy, and the location was great. The house is on a quiet street, just a short walk to the water and a very quick drive to great food options. After checking out the restaurants and shops, we made sure to stock up on some treats to bring home from the Italian deli as well as the fresh pasta shop in town. The space itself was thoughtfully designed, stylish, and immaculately clean. Patricia, the host, was friendly, very accommodating, and helpful. Definitely recommended for anyone looking for a comfortable and hassle-free stay!