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Port Chester Holiday Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Port Chester holiday rentals

Private kitchen
Starlight Hotel

Aparthotel in Queens

Starlight Hotel
2.5 star property
8.0 out of 10, Very good, (763)
"Yes room was very clean , quiet and staff was great."
United States
John
The price is HK$847
HK$1,000 total
includes taxes & fees
18 Dec - 19 Dec
Starlight Hotel
Exterior
Global Luxury Suites at The Arches

Aparthotel in Bronx

Global Luxury Suites at The Arches
2.5 star property
6.8 out of 10, (540)
"Enjoyed our stay , would stay again "
United States
Dawnae
Global Luxury Suites at The Arches
Exterior
Stamford Suites

Aparthotel in Downtown Stamford

Stamford Suites
4.0 star property
6.2 out of 10, (79)
"It was great"
United States
Natalie
The price is HK$859
HK$988 total
includes taxes & fees
23 Dec - 24 Dec
Stamford Suites
Smart TV
Beautiful cozy two bedroom apartment in great location of NYC!!

Apartment in Manhattan

Beautiful cozy two bedroom apartment in great location of NYC!!
8.6 out of 10, Excellent, (41)
"It was cute and close to Yankee Stadium "
United States
Christina C.
Beautiful cozy two bedroom apartment in great location of NYC!!
Living area
Spacious 3BR Luxe Escape near NYC

Apartment in Southeast Yonkers

Spacious 3BR Luxe Escape near NYC
2.0 star property
The price is HK$1,549
HK$2,503 total
includes taxes & fees
12 Jan - 13 Jan 2026
Spacious 3BR Luxe Escape near NYC
Reception
Global Luxury Suites White Plains

Apartment in White Plains

Global Luxury Suites White Plains
3.5 star property
6.8 out of 10, (34)
"Great location, spacious apartment and clean. The public areas like the hallway needed vacuuming but everything else was great."
United States
Jennifer
Global Luxury Suites White Plains
Smart TV, fireplace
Modern 1-bedroom Garden Apartment with Backyard, up to 25 mins to Times Square

Apartment in Manhattan

Modern 1-bedroom Garden Apartment with Backyard, up to 25 mins to Times Square
2.0 star property
10.0 out of 10, Exceptional, (62)
"Great place. Very clean, quiet, really nice patio, and close to the subway. Much better than getting a hotel room. "
United States
Christopher C.
Modern 1-bedroom Garden Apartment with Backyard, up to 25 mins to Times Square
Property entrance
Guesthouse at Norwalk Inn

Aparthotel in Historic District

Guesthouse at Norwalk Inn
3.5 star property
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$2,063
HK$2,373 total
includes taxes & fees
2 Jan - 3 Jan 2026
Guesthouse at Norwalk Inn
Dining
Luxury & Elegance @ Large Private HOME, 3baths, CentralAC, Washer/Dryer, Parking

Apartment in Bronx

Luxury & Elegance @ Large Private HOME, 3baths, CentralAC, Washer/Dryer, Parking
2.0 star property
8.8 out of 10, Excellent, (8)
"I recently stayed in this apartment and absolutely loved it! The place was spotless, modern, and beautifully decorated. The kitchen was fully equipped with everything I needed, and the bed was super comfortable. The living room had a cozy vibe, perfect for relaxing after a long day. The location couldn’t be better — close to shops, restaurants, and public transport, yet quiet enough for a good night’s sleep. The host was incredibly friendly and responsive, making check-in and check-out smooth...
United States
Hemza
The price is HK$1,595
HK$4,816 total
includes taxes & fees
19 Dec - 20 Dec
Luxury & Elegance @ Large Private HOME, 3baths, CentralAC, Washer/Dryer, Parking
Private kitchen
3BR Prime Luxury near NYC w Arcade Room

Holiday Home in Southeast Yonkers

3BR Prime Luxury near NYC w Arcade Room
2.0 star property
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$1,938
HK$2,938 total
includes taxes & fees
12 Jan - 13 Jan 2026
3BR Prime Luxury near NYC w Arcade Room
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Holiday Home in Greenwich

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
9.6 out of 10, Exceptional, (23)
"This was a great place! The host George and his wife were incredibly helpful and so nice, making the stay even better. I would absolutely recommend this spot to anyone and definitely plan to be back again!"
United States
Alexus C.
The price is HK$1,146
HK$2,260 total
includes taxes & fees
20 Dec - 21 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Dining
Modern Comfort in the Heart of NYC

Apartment in Southeast Yonkers

Modern Comfort in the Heart of NYC
4.0 star property
The price is HK$3,502
HK$4,688 total
includes taxes & fees
17 Dec - 18 Dec
Modern Comfort in the Heart of NYC
Lounge
Luxury Apartments by Hyatus at The Asher

Aparthotel in Downtown Stamford

Luxury Apartments by Hyatus at The Asher
4.5 star property
10.0 out of 10, Exceptional, (19)
"Clean and had everything you need for longer stay Comfortable "
United States
christine
Luxury Apartments by Hyatus at The Asher
Property grounds
Beautiful 1-bedroom condo in New York, Manhattan Central Park Times Square

Condo in Manhattan

Beautiful 1-bedroom condo in New York, Manhattan Central Park Times Square
Beautiful 1-bedroom condo in New York, Manhattan Central Park Times Square
Dining
Luxury NYC Home with Free Parking for 12

Villa in White Plains

Luxury NYC Home with Free Parking for 12
4.0 star property
The price is HK$3,502
HK$5,293 total
includes taxes & fees
17 Dec - 18 Dec
Luxury NYC Home with Free Parking for 12
Living area
Modern Luxury Home w GameRoom & Parking

Holiday Home in Southeast Yonkers

Modern Luxury Home w GameRoom & Parking
3.0 star property
7.2 out of 10, Good, (5)
"This was an excellent House My birthday weekend was amazing I totally would book again"
United States
Keisheena
Modern Luxury Home w GameRoom & Parking
Fridge, microwave, oven, stovetop
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Apartment in Bronx

Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC
9.0 out of 10, Wonderful, (8)
"We had a wonderful time. The apartment was exactly as described in the posting. Every room was super clean, bright, and welcoming. We were very comfortable. Eche was very helpful. We appreciated how quickly he responded to our questions. He checked in with us and made sure we had everything we needed. Many nice extra touches made us feel at home. We plan to stay here next time we are in town!"
United States
Karen C.
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC
Smart TV
Sprawling 2BR w King Bed, fast WiFi, 20 minutes to Times Square!

Apartment in Bronx

Sprawling 2BR w King Bed, fast WiFi, 20 minutes to Times Square!
10.0 out of 10, Exceptional, (23)
"We loved our stay at this condo! It was very comfortable and easy access to the subway! The host was very gracious. I would definitely stay again at this location."
United States
Diane P.
The price is HK$2,724
HK$4,850 total
includes taxes & fees
6 Jan - 7 Jan 2026
Sprawling 2BR w King Bed, fast WiFi, 20 minutes to Times Square!
Dining
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Holiday Home in Northeast Yonkers

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
8.6 out of 10, Excellent, (45)
"Very clean property in a quiet neighborhood. Convenient shopping only minutes away (including a Costco). We would definitely stay there again."
United States
Dan F.
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Property grounds
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

Apartment in Scarsdale

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
9.2 out of 10, Wonderful, (5)
"The owner was very responsive and kind. The apartment was very clean and well updated. We are older adults and the access to the basement apartment was a bit of a challenge but the owner did graciously help with our luggage. The family does clearly disclose that they live above the unit and sounds of children may be heard. Between the sounds of the family above and the fact it’s a basement, not a “Loft”, with all the plumbing just above your head - it was not for us. "
United States
Annette D.
The price is HK$1,323
HK$2,492 total
includes taxes & fees
14 Jan - 15 Jan 2026
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic
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

Radio Hotel

Radio Hotel

10/10 Excellent
"Yup"
Tommy 4-night trip
Posted 23 hours ago
Radio Hotel

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.