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Vacation rentals in Port Chester

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Top-rated vacation rentals in Port Chester

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Rental unit in Downtown Stamford

4.96 out of 5 average rating, 168 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!

Home in White Plains

4.86 out of 5 average rating, 180 reviews

Bright&Comfy 2bed/1ba in quiet duplex

Bright, comfortable & quiet! Just outside downtown White Plains, this home has a relaxing living space with thoughtful touches. It offers easy accessibility to New York City (35 min Via Metro North) and Westchester (via highways and local buses). The house is set up for WFH, with great wifi via Verizon. It's an easy jump off spot for a fun weekend in Westchester. It comes with a dedicated parking spot, never worry about your vehicle! Bars, restaurants, shopping, groceries are all minutes away!

Guest suite in Bayville

4.92 out of 5 average rating, 487 reviews

Romantic, Cozy and Private, 1 Block from Beach

Relax in your private romantic retreat with Canopy Queen Bed & Beautiful modern bathroom, 1 Block from beach, Second floor studio with small fridge, microwave, coffee maker, induction cook top, SmartTV... Just 7 min from the Long Island Railroad, Oyster Bay stop. Near to restaurants, shops, tennis courts. You can go biking, swimming, fishing, play golf, rent kayaks, motor boats, paddle boards. Visit Arboretums, Historic sites, Parks, walk along the water, go to the nearby movies and more...

Rental unit in Rye Brook

4.81 out of 5 average rating, 357 reviews

Musicians HiTech Launch Pad- CAPITOL Theater & NYC

Comfortable and well stocked High Tech apartment delivers a great place to rest, work, and play. Less than 1 mile from Capital Theater and Port Chester metro North. 40 min express to NYC. Massive 85" Sony UHD4K Android smart TV with 300+ movie library on Google play, HBO, Netflix, and Hulu (w/ live TV). Bose surround sound. 3 x desks with 32" monitors for computer dock + streaming TV (Roku). XBOX. Board Games. Poker. Well stocked Eat in Kitchen with pub Height Table for 6.

Townhouse in Greenwich

4.92 out of 5 average rating, 114 reviews

Walk to Greenwich Ave [KING bed] BEST Location

Sun drenched unit in the heart ♥️of Greenwich by a Superhost :) Enjoy a quick walk to the bustling Greenwich Ave and all it offers, train station, Whole Foods, wonderful restaurants and night life. This spacious duplex unit with private entrance, private outdoor area & excellent soundproofing gives you the feel, QUIET and privacy of an in-town single family home. This perfect location is a nice getaway or a WFH stay with KING bed, Full kitchen, updated appliances, Speedy WiFi⚡️& SMART TVs

Guest suite in Cos Cob

4.9 out of 5 average rating, 473 reviews

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.

Guest suite in White Plains

4.93 out of 5 average rating, 156 reviews

Convenient go to NYC, close to White Plains R.R.

From NYC by train 37 minutes, and walking from my apartment to the train is only 7 minutes, but coming back is uphill so it takes longer. Please read the entire description, and make sure the place, you are looking for, before you reserve. Convenient for shopping, dining, and walking distance to downtown White plains. My apartments are located on the 2nd Floor of my house. You can reach from the parking lot directly, a stairways cover by an awning.

Rental unit in Harrison

4.96 out of 5 average rating, 274 reviews

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.

Rental unit in Ardsley

4.89 out of 5 average rating, 411 reviews

Lovely and Well Appointed Suite w/ Indoor Parking

Charming suite with a private entrance, bathroom, indoor parking and dining area with kitchen amenities. Conveniently located in Westchester, and is accessible by the I-87, Henry Hudson, Sprain and Saw Mill Parkways; only a thirty minute drive to NYC. Near a deli, grocery, bakery, Carvel, CVS and a selection of restaurants.

Home in Stamford

4.99 out of 5 average rating, 152 reviews

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.

Cottage in Valhalla

4.96 out of 5 average rating, 262 reviews

Charming private 1BR apt. Easy access to NYC

Location, location, location! Private 1 bedroom unit that is part of a two-unit property. It has its own entrance, kitchen, bath, and off street parking. Walkable to Valhalla Metro North train station. (Has steps and stairs. No children under 12 years old.)

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

Free parking on premises

Air conditioning

Stay near Port Chester's top sights

The Capitol Theatre22 locals recommend

AMC Port Chester 1411 locals recommend

Little Thai Kitchen7 locals recommend

Costco Wholesale6 locals recommend

PepsiCo6 locals recommend

Citarella Gourmet Market - Greenwich, CT5 locals recommend

Other great vacation rentals in Port Chester

Home in Port Chester

5 out of 5 average rating, 10 reviews

Labrador Manor: Westchester County Home with Pool

Cottage in Rye

5 out of 5 average rating, 36 reviews

Rye Cottage - Walk to Beach & Playland

Home in Rye

4.92 out of 5 average rating, 85 reviews

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

Guest suite in Cos Cob

5 out of 5 average rating, 12 reviews

Cozy Cos Cob Studio

Guesthouse in Old Greenwich

4.89 out of 5 average rating, 45 reviews

Cozy brand new guest home

Rental unit in Norwalk

4.96 out of 5 average rating, 23 reviews

Cozy, functional, soothing

Rental unit in Pleasantville

4.82 out of 5 average rating, 57 reviews

Beautiful Studio Apartment in Perfect Location

Rental unit in Stamford

4.81 out of 5 average rating, 83 reviews

Cozy guest apartment

Quick stats about vacation rentals in Port Chester

Total rentals
30 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Frequently Asked Questions

Are there family-friendly vacation rentals in Port Chester?
Port Chester has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Port Chester?
Experience the best of Port Chester with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Port Chester?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Port Chester have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Port Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Port Chester have free parking?
Absolutely! We offer over 10 house rentals with free parking in Port Chester. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Port Chester?
Yes! Work meets play with ease at over 20 vacation rentals in Port Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Port Chester?
Four-legged friends are welcome in Port Chester. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Port Chester have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Port Chester. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore