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Top Holiday Rentals in Port Chester

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

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

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

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

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

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

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 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 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

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

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

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

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 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

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!

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

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.