Port Chester Holiday Rentals

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Port Chester holiday rentals

Private kitchen
Starlight Hotel

Starlight Hotel

Starlight Hotel
2.5 star property
Queens
8.0 out of 10, Very good, (755)
"Yes room was very clean , quiet and staff was great."
United States
John
The price is HK$856
HK$1,010 total
includes taxes & fees
4 Jan - 5 Jan 2026
Starlight Hotel
Exterior
Stamford Suites

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (78)
"It was great"
United States
Natalie
The price is HK$932
HK$1,071 total
includes taxes & fees
21 Dec - 22 Dec
Stamford Suites
Living area
The Mansion Hotel-style

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.6 out of 10, Excellent, (19)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is HK$751
HK$864 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Mansion Hotel-style
Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.4 out of 10, Very good, (40)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is HK$1,955
HK$2,248 total
includes taxes & fees
2 Jan - 3 Jan 2026
Guesthouse at Norwalk Inn
Exterior
Global Luxury Suites at The Arches

Global Luxury Suites at The Arches

Global Luxury Suites at The Arches
2.5 star property
Bronx
6.8 out of 10, (537)
"Enjoyed our stay , would stay again "
United States
Dawnae
Global Luxury Suites at The Arches
Interior
Gold Coast Getaway! Upscale Apt Near New Canaan

Gold Coast Getaway! Upscale Apt Near New Canaan

Gold Coast Getaway! Upscale Apt Near New Canaan
3.0 star property
West Norwalk
The price is HK$1,711
HK$2,762 total
includes taxes & fees
14 Dec - 15 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan
Dining
Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
The price is HK$3,501
HK$5,292 total
includes taxes & fees
12 Dec - 13 Dec
Luxury NYC Home with Free Parking for 12
Living area
Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
The price is HK$3,493
HK$5,067 total
includes taxes & fees
14 Dec - 15 Dec
Luxury 5 BR Home Free Parking
Living area
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is HK$2,606
HK$3,686 total
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 3BR Luxe Escape near NYC
Dining
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
The price is HK$3,501
HK$4,687 total
includes taxes & fees
14 Dec - 15 Dec
Modern Comfort in the Heart of NYC
Living area
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
The price is HK$3,105
HK$4,244 total
includes taxes & fees
11 Jan - 12 Jan 2026
Spacious 3BR Luxe Escape near NYC
5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow
2.0 star property
Ossining
The price is HK$3,211
HK$7,248 total
includes taxes & fees
5 Jan - 6 Jan 2026
Foliage at Westchester Manor - Near Sleepy Hollow
Private kitchen
3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
United States
Anonymous traveller
The price is HK$3,105
HK$4,244 total
includes taxes & fees
11 Jan - 12 Jan 2026
3BR Prime Luxury near NYC w Arcade Room
Living area
Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking

Luxury NY Home 3BR with Easy Parking
3.0 star property
Southeast Yonkers
3.0 out of 10, (4)
"There was nothing luxury about this place. Please dont let the pictures fool you and its non refundable. Communication is horrible. They even tried charging cleaning fee for a dirty house, i took a total loss and just stayed at hotels "
United States
Jose
The price is HK$2,933
HK$4,051 total
includes taxes & fees
14 Dec - 15 Dec
Luxury NY Home 3BR with Easy Parking
Interior
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

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

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is HK$739
HK$1,917 total
includes taxes & fees
22 Dec - 23 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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.
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Top Port Chester Hotel Reviews

New York LaGuardia Airport Marriott

New York LaGuardia Airport Marriott

10/10 Excellent
"The staff was wonderful and efficient, they had a nice breakfast buffet and the room was clean and nice. "
Betty 2-night trip
Posted 2 days ago
New York LaGuardia Airport Marriott

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 holiday rental in Port Chester?

Yes, there are holiday rentals close to the most popular sights in Port Chester, or you can select a more secluded option if you're looking for a relaxing stay. Port Chester is known for its live music and entertainment choices. Make sure you have time to check out the theatres and waterfront during your trip.

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

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Port Chester is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Port Chester?

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

What can I see and do in Port Chester?

Cultural attractions to visit include Capitol Theatre and Clay Art Center Gallery. In the wider area, you’ll find Rye Playland and Bruce Museum of Arts and Science.

What are holiday rentals like in Port Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Port Chester. Holiday rentals provide amenities such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for small groups.