Vacation rentals in Port Chester

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Top-rated vacation rentals in Port Chester

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Guest favorite

Apartment in Stamford

4.97 out of 5 average rating, 122 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!

Feb 21 – 28

R2,677 ZAR per night

Superhost

Apartment in Stamford

4.82 out of 5 average rating, 146 reviews

Sunset Retreat: 1BR Walking Distance to the Beach

Welcome to our charming and spacious 1 bedroom Airbnb in the heart of the beach district in Stamford! This delightful 1st fl apartment offers everything you need for a memorable stay. Prime location offers the best of both worlds. Just a short 5-min stroll will take you to the local train station, providing easy access to neighboring cities and attractions. Additionally, downtown Stamford is a mere 7-min drive, where you can indulge in a wide array of dining, shopping, and entertainment options.

Feb 22 – Mar 1

R2,509 ZAR per night

Guest favorite

Guest suite in Hartsdale

4.88 out of 5 average rating, 114 reviews

Haven in Hartsdale! Private guest suite & bathroom

This is a listing for a sparkling clean self-contained basement-level guest suite within our home. You have your own entrance and complete privacy as well as your own private shower room. My husband and I live in the property above with our cat. While he will not have access to your suite, I respectfully advise if you have allergies or just a general dislike of cats then this is not the place for you. The suite comes complete with a microwave, mini fridge, iron & tea & coffee making facilities.

Jul 5 – 12

R2,225 ZAR per night

Guest favorite

Home in White Plains

4.86 out of 5 average rating, 148 reviews

Bright&Comfy 2bed/1ba in quiet White Plains 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!

Aug 20 – 27

R3,393 ZAR per night

Guest favorite

Guest suite in Bayville

4.91 out of 5 average rating, 426 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...

Dec 4 – 11

R1,625 ZAR per night

Guest favorite

Guesthouse in Norwalk

4.99 out of 5 average rating, 208 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

Aug 23 – 30

R2,230 ZAR per night

Guest favorite

Apartment in Rye Brook

4.81 out of 5 average rating, 333 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.

Sep 24 – Oct 1

R4,814 ZAR per night

Guest favorite

Guest suite in Greenwich

4.91 out of 5 average rating, 429 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.

Jul 2 – 9

R4,002 ZAR per night

Guest favorite

Guest suite in White Plains

4.87 out of 5 average rating, 164 reviews

1BR close to White Plains train station

From NYC by train 40 minutes, and walking from my apartment to the train only 7 minutes, but coming back is uphill so takes longer. Convenient for shopping, and dining, and walking distance to downtown White plains. Please read the entire description, and make sure the place, you are looking for, before you reserve. Our apartments are completely renovated and have separate entrances. Please ask me a monthly rate.

Oct 11 – 18

R2,889 ZAR per night

Guest favorite

Apartment in Harrison

4.96 out of 5 average rating, 247 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.

Nov 22 – 29

R2,464 ZAR per night

Guest favorite

Apartment in Port Chester

5.0 out of 5 average rating, 21 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.

Sep 24 – Oct 1

R4,068 ZAR per night

Guest favorite

Apartment in Ardsley

4.9 out of 5 average rating, 380 reviews

Lovely and well-appointed suite with full privacy

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.

Apr 16 – 23

R2,036 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Port Chester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Port Chester's top sights

The Capitol Theatre22 locals recommend

Costco Wholesale6 locals recommend

AMC Port Chester 1411 locals recommend

Stop & Shop3 locals recommend

Pollo A La Brasa3 locals recommend

Acuario3 locals recommend

Other great vacation rentals in Port Chester

Guest favorite

Apartment in Harrison

5.0 out of 5 average rating, 29 reviews

Cozy Studio Ideal For Travelers & Commuters

Mar 26 – Apr 2

R2,732 ZAR per night

Guest favorite

Apartment in Harrison

4.89 out of 5 average rating, 47 reviews

Quiet and Cozy

Sep 28 – Oct 5

R1,761 ZAR per night

Guest favorite

Guesthouse in Greenwich

4.88 out of 5 average rating, 82 reviews

Overlook Cabin in downtown Greenwich CT

Sep 29 – Oct 6

R1,769 ZAR per night

Guest favorite

Apartment in Stamford

4.86 out of 5 average rating, 44 reviews

Stamford’s Island Inspired Efficiency

Sep 21 – 28

R1,657 ZAR per night

Guest favorite

Apartment in Greenwich

4.96 out of 5 average rating, 72 reviews

Cozy 2 BR Greenwich Apt. with easy access to NYC

Aug 18 – 25

R3,299 ZAR per night

Guest favorite

Apartment in Rye Brook

4.93 out of 5 average rating, 15 reviews

Cozy studio near Port Chester.

Nov 30 – Dec 7

R2,559 ZAR per night

Guest favorite

Home in White Plains

4.91 out of 5 average rating, 11 reviews

Charming Victorian Retreat for Two

Mar 2 – 9

R2,720 ZAR per night

Guest favorite

Apartment in Stamford

5.0 out of 5 average rating, 53 reviews

Standalone Cottage surrounded by woods

Mar 9 – 16

R2,081 ZAR per night

Show all

Quick stats about vacation rentals in Port Chester

Total rentals
30 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
R955 ZAR before taxes and fees

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.
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 $50 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 air conditioning, over 10 homes with a kitchen, over 10 homes with free parking, 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.

Vacation rentals in Port Chester

Top-rated vacation rentals in Port Chester

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Port Chester vacation rentals

Stay near Port Chester's top sights

Other great vacation rentals in Port Chester

Apartment in Harrison

Apartment in Harrison

Guesthouse in Greenwich

Apartment in Stamford

Apartment in Greenwich

Apartment in Rye Brook

Home in White Plains

Apartment in Stamford

Quick stats about vacation rentals in Port Chester

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there family-friendly vacation rentals in Port Chester?

How much does it cost to stay in house rentals in Port Chester?

What are the most popular amenities for House Rentals in Port Chester?

Do house rentals in Port Chester have air conditioning?

Do house rentals in Port Chester have free parking?

Are there vacation rentals with a dedicated workspace in Port Chester?

Are there pet-friendly vacation rentals in Port Chester?

Do house rentals in Port Chester have a kitchen?

Destinations to explore