
Holiday houses in Port Chester
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Top-rated holiday rentals in Port Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

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!

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!

Flex Comfort Apts of Greenwich #2
Flex Comfort Apt #2 is 2 Bedroom / 1 Bath and sleeps 4. Apt #2 is the middle floor of a 3 apartment building. Private Parking & Entrance. Great mattresses, linens, big screen smart TVs, multiple desks, and clean. Well stocked kitchen to put on a family meal. Get the value of 2 x hotel rooms for the price of one that includes your own kitchen and Family Room. 1 Mile from Greenwich Train station - 45 mins to Grand Central. Easy access to 95 and everything CT & NY have to offer.

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

Walk to Train! Entire Family Home w Parking + Yard
Experience the charm of a historic, family-friendly neighborhood just 40 minutes from NYC. ✔ Entire Private Home (full duplex used as one single-family home) ✔ Modern, Fully Equipped Kitchen w/ Stainless Steel Appliances ✔ On-site Washer & Dryer ✔ Fios Gigabit Wi-Fi — perfect for remote work ✔ 13-minute walk to the train | ~40-minute ride to NYC ✔ 2-minute walk to park with tennis & basketball courts + playground ✔ Private Fenced Yard — great for kids ✔ Free Driveway Parking for 2 Cars

Cozy 2 BR Greenwich Apt. with easy access to NYC
Cozy two bedroom apartment on a quiet street in Greenwich with brand new appliances. Walking distance to Metro North train station, beach, park, tennis court, pickle ball court, restaurants, shops. Just 38 minutes from NYC. Few minutes drive to downtown. Fully stocked kitchen and laundry with everything you may need. Living room with 65" Smart TV. Master BR with 45" Smart TV. The apartment is professionally cleaned & sanitized up to CDC guidelines & inspected before each stay.

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.

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.

Captain's Cottage on Working Farm with Animals
Charming, fully renovated cottage with cathedral ceilings and private deck. Home has a separate queen bedroom, kitchen and living room on the main floor with small stove fireplace. There is a small loft on the 2nd floor with 2 twin beds accessed by a library ladder (note: no standing headroom in loft). Private outdoor deck with seating and BBQ. Fast wi-fi, laundry access and pet friendly.

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.

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.

Standalone Cottage surrounded by woods
Cottage on property in North Stamford. 20 minutes from Stamford Town Centre. Less than hour train to New York City. Sleeps 4 comfortably (pullout couch in living room, plus main room). Away from main house and surrounded by wooded area.
Popular amenities for Port Chester holiday rentals
Other great holiday rentals in Port Chester

Westchester County quiet neighborhood

Rye Cottage - Walk to Beach & Playland

Quaint duplex + pvt yard-Walk to town/train/beach!

Guest Suite w/ Private Entrance

The Port Chester's star

Cozy Suite near Downtown Pleasantville

Private farm cottage +hiking

Nyack Retreat
When is the best time to visit Port Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $327 AUD | $334 AUD | $298 AUD | $359 AUD | $370 AUD | $403 AUD | $418 AUD | $379 AUD | $400 AUD | $416 AUD | $422 AUD | $426 AUD |
| Avg. temp | 1°C | 2°C | 6°C | 12°C | 18°C | 23°C | 26°C | 25°C | 22°C | 15°C | 10°C | 4°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Port Chester?
Port Chester has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
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.
Are there vacation rentals with a dedicated workspace in Port Chester?
Yes! Work meets play with ease at over 10 vacation rentals in Port Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Where should I stay in Port Chester?
Make yourself at home in Port Chester by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Tamarack Gardens, over 200 vacation rentals in Pemberwick, and over 140 vacation rentals in Port Chester.
Quick stats about holiday rentals in Port Chester

Total holiday rentals
Explore 20 holiday rentals in Port Chester

Nightly prices starting at
Port Chester holiday rentals start at $86 AUD per night before taxes and fees

Verified guest reviews
Over 980 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Port Chester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Port Chester rentals

4.9 Average rating
Port Chester stays are highly rated by guests—averaging 4.9 out of 5!
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- Times Square
- Rockefeller Center
- Madison Square Garden
- Bryant Park
- Brooklyn Bridge
- Columbia University
- Central Park Zoo
- MetLife Stadium
- Yale University
- Mountain Creek Resort
- Bronx Zoo
- Old Glory Park
- Grand Central Terminal
- Ohel Chabad-Lubavitch
- Yankee Stadium
- United Nations Headquarters
- Jones Beach
- Chabad Lubavitch World Headquarters
- Empire State Building
- Citi Field
- Statue of Liberty
- Radio City Music Hall
- Fairfield Beach
- USTA Billie Jean King National Tennis Center




