A suspension bridge over a calm river, surrounded by hills and autumn foliage.

Port Chester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Port Chester vacation rentals

A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

1. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is P20,743
P31,837 total
includes taxes & fees
Nov 9 - Nov 10
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is P10,340
P11,891 total
includes taxes & fees
Nov 9 - Nov 10
Stamford Suites
A breakfast buffet with pastries, fruits, and a coffee station.

3. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is P56,743
P72,592 total
includes taxes & fees
Nov 9 - Nov 10
3BR Prime Luxury NY - Free Parking
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

4. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is P21,373
P24,579 total
includes taxes & fees
Dec 1 - Dec 2
Guesthouse at Norwalk Inn
A modern interior with a sectional sofa, a glass wall, and a wooden bookshelf.

5. The Arches Suites

The Arches Suites
2.0 star property
Bronx
The price is P9,136
P17,009 total
includes taxes & fees
Nov 17 - Nov 18
The Arches Suites
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

6. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is P30,928
P64,331 total
includes taxes & fees
Nov 9 - Nov 10
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

7. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.0 out of 10, (12 reviews)
"Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ... Will use this management and property owner in our upcoming short terms rentals....."
United States
abdelwahab
Modern Luxury Home w GameRoom & Parking
A two-story house with a front porch, a garage, and a well-maintained lawn.

8. Great Neck Basecamp: Steps to Downtown & Rail

Great Neck Basecamp: Steps to Downtown & Rail
3.0 star property
Great Neck
The price is P9,079
P25,200 total
includes taxes & fees
Nov 11 - Nov 12
Great Neck Basecamp: Steps to Downtown & Rail
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Port Chester Hotel Reviews

Executive Inn - Fort Lee

Executive Inn - Fort Lee

8/10 Good
"Amazing stay as always ! Just one feedback , please ensure extended stays are documented accordingly . My lady and I got woken up because the housekeeper was unaware our stay was extended until 6… then the house keeper informed me to call front desk and confirm. I always enjoy our stay , just had this one feedback"
Dwight 1-night trip
Posted 3 hours ago
Executive Inn - Fort Lee

Find out more about Port Chester

Search for holiday rentals in Port Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Port Chester using one of the methods below:

  • View our selection of featured holiday rentals in Port Chester
  • Use the map to find apartments and other holiday homes in the Port Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Port Chester while they last

Look no further and take a look at our great range of rental properties in Port Chester!

Frequently asked questions

Can I find a vacation rental in Port Chester?

Yes, you can find vacation rentals in Port Chester close to Port Chester-Rye Brook Public Library, or you can select a secluded option if you're looking for extra privacy while you relax. Port Chester is known for its live music and entertainment choices. Make sure you have time to check out the theaters and waterfront during your trip.

What are some of the best vacation rentals that Port Chester has to offer?

Modern Luxury Home w GameRoom & Parking: You might want to consider this vacation rental near Port Chester, which is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Port Chester?

With 4 Expedia vacation rentals, you're sure to find just the right place for your Port Chester stay.

What can I see and do in Port Chester?

Enjoy the area's cultural attractions such as Capitol Theatre, or get outdoors into nature at a spot like Hawthorne Beach. While here, Capitol Theatre - Garcia’s and Port Chester-Rye Brook Public Library are other places worth a visit.

What are vacation rentals like in Port Chester?

Vacation rentals are privately owned properties you can book for a couple days or more in Port Chester. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.