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Port Chester Holiday Rentals

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Check prices for these dates

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Port Chester holiday rentals

Fridge, microwave, dishwasher, toaster
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (28)
"10/10 Excellent Ms.Carmen is an amazing host. Prompt communication. Apartment is very clean, private and it had everything we needed. We will ALWAYS stay here when visiting Port Chester. "
United States
Amanda
The price is HK$1,710
HK$3,004 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Private kitchen
The Mansion Hotel-style

The Mansion Hotel-style

The Mansion Hotel-style
2.5 star property
West Norwalk
8.2 out of 10, Very good, (22)
"Great service and very clean 👌 "
United States
JEAN
The price is HK$644
HK$741 total
includes taxes & fees
30 Dec - 31 Dec
The Mansion Hotel-style
Property entrance
Starlight Hotel

Starlight Hotel

Starlight Hotel
2.5 star property
Queens
8.0 out of 10, Very good, (773)
"Clean room, very large with good amenities"
United States
Benjamin
The price is HK$837
HK$988 total
includes taxes & fees
4 Jan - 5 Jan 2026
Starlight Hotel
Private kitchen
JayZero

JayZero

JayZero
2.0 star property
Bryn Mawr
The price is HK$769
HK$2,019 total
includes taxes & fees
15 Jan - 16 Jan 2026
JayZero
Interior
Charming Apartment in Quiet Neighborhood

Charming Apartment in Quiet Neighborhood

Charming Apartment in Quiet Neighborhood
Tappan
10.0 out of 10, Exceptional, (20)
"The location was perfect for our visit and the apartment was immaculately clean and well stocked."
United States
Claudia M.
The price is HK$762
HK$1,471 total
includes taxes & fees
14 Jan - 15 Jan 2026
Charming Apartment in Quiet Neighborhood
Exterior
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (2)
"Great stay!"
United States
Ann S.
The price is HK$808
HK$1,884 total
includes taxes & fees
4 Jan - 5 Jan 2026
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (23)
"The hosts were very friendly and very accommodating. "
United States
Daniel C.
The price is HK$944
HK$2,003 total
includes taxes & fees
12 Jan - 13 Jan 2026
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
1 bedroom, in-room safe, desk, free WiFi
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
9.2 out of 10, Wonderful, (9)
"Had a great stay "
United States
Desiree
The price is HK$699
HK$1,215 total
includes taxes & fees
2 Jan - 3 Jan 2026
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Private kitchen
Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is HK$777
HK$2,047 total
includes taxes & fees
26 Jan - 27 Jan 2026
Elegant Hideaway with Free Parking
Living area
Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
The price is HK$855
HK$2,114 total
includes taxes & fees
11 Jan - 12 Jan 2026
Luxe 1BR Oasis - Prime NY Stay
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$1,220
HK$2,469 total
includes taxes & fees
30 Dec - 31 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
2 bedrooms, in-room safe, desk, iron/ironing board
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food

Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (90)
"I had a great stay at this extremely comfortable home in a quiet neighborhood. Maria was very welcoming and helpful. I hope to visit and stay here again soon."
United States
Jill D.
The price is HK$873
HK$2,128 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfortable 2bd⭐ Convenience & Style ⭐45min to NYC,Great Food
Lobby
Stamford Suites

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (84)
"Everything was good other than the two options for breakfast and housekeeping entering the hotel room unannounced or no knocking"
United States
Laila
The price is HK$858
HK$987 total
includes taxes & fees
30 Dec - 31 Dec
Stamford Suites
Interior
1-bedroom apartment with AC in Syosset

1-bedroom apartment with AC in Syosset

1-bedroom apartment with AC in Syosset
2.0 star property
Syosset
The price is HK$1,119
HK$3,331 total
includes taxes & fees
4 Jan - 5 Jan 2026
1-bedroom apartment with AC in Syosset
Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is HK$2,103
HK$2,419 total
includes taxes & fees
30 Dec - 31 Dec
Guesthouse at Norwalk Inn
Fridge, microwave, oven, stovetop
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (6)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is HK$1,034
HK$2,364 total
includes taxes & fees
4 Jan - 5 Jan 2026
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Internet, bed sheets
Fantastic bedroom with AC & fireplace in home in charming Mount Vernon

Fantastic bedroom with AC & fireplace in home in charming Mount Vernon

Fantastic bedroom with AC & fireplace in home in charming Mount Vernon
South Side
The price is HK$769
HK$1,030 total
includes taxes & fees
30 Dec - 31 Dec
Fantastic bedroom with AC & fireplace in home in charming Mount Vernon
Private kitchen
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$1,546
HK$2,499 total
includes taxes & fees
12 Jan - 13 Jan 2026
Spacious 3BR Luxe Escape near NYC
Terrace/patio
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
8.2 out of 10, Very good, (18)
"Great place great location"
United States
Daquan H.
The price is HK$734
HK$1,048 total
includes taxes & fees
8 Jan - 9 Jan 2026
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Property grounds
Piermont Oasis

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (10)
"Easy check in; quick access to NYC. "
United States
Leah B.
The price is HK$933
HK$1,636 total
includes taxes & fees
11 Jan - 12 Jan 2026
Piermont Oasis
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

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

10/10 Excellent
"Awesome team! Very clean!"
Nerva 1-night trip
Posted 2 days ago
EVEN Hotel Norwalk by IHG

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.