Holiday rentals in Port Chester

4.9 out of 5 average rating, 112 reviews

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!

4.92 out of 5 average rating, 119 reviews

Home in Highlands

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!

5 out of 5 average rating, 17 reviews

Home in Port Chester

3br + game rm abt 45min drive or easy train to NYC

This cozy 3-bedroom Port Chester house (accommodates up to 11 people), offers excellent value, spacious living, and proximity to NYC and Greenwich, CT. A short 10-min walk brings you to the center, the historic Capitol Theatre, & the train to NYC. It's a quick drive to key landmarks and attractions, about 40 mins to NYC, with a train ride to Grand Central taking 45-60 mins. 11-min walk to Capitol Theatre. Perfect for those seeking a quiet, safe neighborhood close to the vibrant city centers.

Guest house in Mamaroneck

5 out of 5 average rating, 39 reviews

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, 118 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

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.

4.81 out of 5 average rating, 104 reviews

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

Flat 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.

4.95 out of 5 average rating, 74 reviews

Townhouse in Greenwich

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, 93 reviews

Guest house 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.

4.96 out of 5 average rating, 76 reviews

Flat in Port Chester

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.

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Other great holiday rentals in Port Chester

4.98 out of 5 average rating, 43 reviews

Private room in Stamford

Sun Room

CourtneyRating, 5 stars6 days ago

Carmen was so friendly and responsive, will definitely stay here again thank you!

Private room in Dobbs Ferry

4.94 out of 5 average rating, 373 reviews

Small cozy room in historic 1828 Dobbs Ferry home.

SusanRating, 5 stars2 weeks ago

Joanna is an awesome host and person! She went above and beyond doing everything to help me and make my visit comfortable and fun. Great location too. Walk to everything. Train to NYC is super close. Highly recommend this place!

4.71 out of 5 average rating, 105 reviews

Hotel room in Purchase

Studio with 1 King Bed at Hyatt House White Plains

RubyRating, 5 stars3 weeks ago

Overall the hotel was great. It was a bit far from the places I wanted to visit while on vacation but the neighborhood was nice and quiet. They had the BEST fruit water in the lobby available to everyone and the staff was super nice.

Private room in Riverside

4.9 out of 5 average rating, 214 reviews

Private basement bedroom /bathroom in family home

KellyRating, 5 stars3 days ago

The rooms were immaculate ! It included a bedroom and extra large bathroom. You felt welcomed right from the start, it was warm and cozy. The bed was sooo comfy and inviting, loved it. The bath was amazing. Carolyn had all the right touches from amazing body wash, shampoo and conditioner, various bubble bath options, lotions, you name. You were able to make coffee, having milk in the fridge along with waters and yogurts. She also had quick snacks available. Beautiful setting all around! Even fresh flowers in the rooms! We hope to be able to return in the future! Spectacular job Carolyn!

Private room in Mamaroneck

5 out of 5 average rating, 3 reviews

Maple Ave, twin-size private bedroom near train

CharmianRating, 5 stars1 month ago

Absolutely wonderful stay and May is a very kind flexible host that goes above and beyond to make you feel at home and comfortable. Its a very well located place and I would gladly return, I highly recommend this stay!

4.92 out of 5 average rating, 238 reviews

Private room in Elmsford

1-1 INSIDE OF new Westchester home

DouglasRating, 5 stars5 days ago

We had an amazing stay at Darren and Erin’s home! The house was spotless, and the bedroom was very comfortable. We felt right at home and enjoyed every moment especially interacting with Rue, the French bulldog. Highly recommend to anyone looking for a beautifully decorated and clean place to stay!”

Private room in Fair Lawn

4.96 out of 5 average rating, 139 reviews

A cozy bedroom.

VamshiRating, 5 stars6 days ago

Great place for a quick night stay as I was commuting for work.