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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Top Holiday Rentals in Port Chester

Property entrance
Starlight Hotel

Starlight Hotel

2.5 star property
Queens
8.0 out of 10, Very good, (749)
"Clean room, great location."
United States
Matt
The price is 3.321.990 ₫
3.904.260 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Starlight Hotel
Deluxe Studio Suite, 1 King Bed, Balcony | Balcony view
Global Luxury Suites at The Arches

Global Luxury Suites at The Arches

2.5 star property
Bronx
6.8 out of 10, (536)
"Enjoyed our stay , would stay again "
United States
Dawnae
Global Luxury Suites at The Arches
Exclusive Apartment | Private kitchen | Mini-fridge, microwave, oven, stovetop
The Mansion Hotel-style

The Mansion Hotel-style

2.5 star property
Norwalk
8.4 out of 10, Very good, (16)
"Lovely property in a gorgeous setting. Staff were very responsive and welcoming. "
United States
Holly
The price is 2.372.850 ₫
2.728.778 ₫ total
includes taxes & fees
3 Dec - 4 Dec
The Mansion Hotel-style
Lobby
Stamford Suites

Stamford Suites

4.0 star property
Downtown Stamford
6.2 out of 10, (77)
"It was great"
United States
Natalie
The price is 3.155.890 ₫
3.629.274 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Stamford Suites
Apartment (1 Bedroom) | Interior
Gold Coast Getaway! Upscale Apt Near New Canaan

Gold Coast Getaway! Upscale Apt Near New Canaan

3.0 star property
Norwalk
The price is 3.216.530 ₫
4.570.373 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Gold Coast Getaway! Upscale Apt Near New Canaan
Standard Room, 1 King Bed, Main Building | Property entrance
Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn

3.5 star property
Norwalk
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 7.672.215 ₫
8.823.047 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Guesthouse at Norwalk Inn
Luxury House | Private kitchen
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2.0 star property
Southeast Yonkers
The price is 9.201.385 ₫
12.904.186 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Spacious 3BR Luxe Escape near NYC
Luxury Villa, Garden View | Dining
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 11.864.250 ₫
17.933.143 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Luxury NYC Home with Free Parking for 12
Luxury Villa, Patio | Private kitchen
Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking

2.0 star property
Bryn Mawr
The price is 10.519.635 ₫
15.697.227 ₫ total
includes taxes & fees
8 Dec - 9 Dec
Luxury 5 BR Home Free Parking
Luxury House, Garden View | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4.0 star property
Southeast Yonkers
The price is 10.519.635 ₫
14.378.976 ₫ total
includes taxes & fees
7 Dec - 8 Dec
Modern Comfort in the Heart of NYC
Terrace/patio
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 15.792.635 ₫
20.278.144 ₫ total
includes taxes & fees
5 Dec - 6 Dec
3BR Prime Luxury near NYC w Arcade Room
Luxury House | Living area
Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC

2.0 star property
Southeast Yonkers
The price is 11.864.250 ₫
15.883.265 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Spacious 3BR Luxe Escape near NYC
House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Foliage at Westchester Manor - Near Sleepy Hollow

2.0 star property
Ossining
The price is 11.476.605 ₫
25.247.200 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Foliage at Westchester Manor - Near Sleepy Hollow
Luxury House | Living area | Flat-screen TV
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 9.941.113 ₫
13.732.150 ₫ total
includes taxes & fees
3 Dec - 4 Dec
Luxury NY Home 3BR with Easy Parking
Apartment (1 Bedroom) | Interior
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 2.504.675 ₫
6.088.469 ₫ total
includes taxes & fees
4 Dec - 5 Dec
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
House (6 Bedrooms) | Front of property
High-end Estate in Norwalk: Quiet & Spacious!

High-end Estate in Norwalk: Quiet & Spacious!

3.0 star property
Norwalk
The price is 25.758.605 ₫
34.907.787 ₫ total
includes taxes & fees
4 Dec - 5 Dec
High-end Estate in Norwalk: Quiet & Spacious!
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

Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

10/10 Excellent
"Our room 612 was spotless, and the staff was very kind. We were so glad we went back this year. Thank you. "
Lucieny 2-night trip
Posted 2 days ago
Hyatt Place Fort Lee / George Washington Bridge

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.

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.