A suspension bridge over a calm river, surrounded by hills and autumn foliage.

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Port Chester holiday rentals

Apartment (1 Bedroom) | Interior

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

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is 5.415.740 ₫
9.556.678 ₫ total
includes taxes & fees
23 Jul - 24 Jul
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (140 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is 4.185.686 ₫
4.813.539 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Stamford Suites
Luxury Apartment | Private kitchen

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is 4.708.539 ₫
9.302.603 ₫ total
includes taxes & fees
17 Aug - 18 Aug
Elegant Hideaway with Free Parking
House (5 Bedrooms) | Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is 5.573.904 ₫
18.745.933 ₫ total
includes taxes & fees
22 Jul - 23 Jul
3 Mi to Downtown: Spacious White Plains Home
Luxury Apartment | Living area

NY Luxury Apt Free Parking in PRIME Area

NY Luxury Apt Free Parking in PRIME Area
3.0 star property
Southeast Yonkers
5.8 out of 10, (7 reviews)
"Everything about this place is amazing. Great location, very safe, cozy, clean. Will be back soon!"
United States
Paola
The price is 2.862.981 ₫
7.120.169 ₫ total
includes taxes & fees
19 Aug - 20 Aug
NY Luxury Apt Free Parking in PRIME Area
Villa, Garden View | Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is 10.648.260 ₫
16.096.457 ₫ total
includes taxes & fees
22 Jul - 23 Jul
Luxury NYC Home Game Room Free Parking
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

Highbridge Hotel

Highbridge Hotel

10/10 Excellent
"I only stayed at the hotel for one night, but it was a very pleasant experience. The staff was helpful. I forgot my toothpaste, and they provided me with a travel set. It was someone’s birthday and they offered me a piece of their birthday cake which I thought was so sweet. Being able to get a complementary hot cup of coffee after a long day of traveling and heat up my food in the lobby microwave such a nice convenience. The shower was a nice pressure and the water was hot (if you like hot showers). The bed was clean and soft. I felt very comfortable."
Roxanne 1-night trip
Posted less than an hour ago
Highbridge Hotel

Frequently asked questions

Can I find a holiday rental in Port Chester?

Yes, there are holiday rentals in Port Chester close to Clay Art Center Gallery, 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?

Enjoy the area's cultural attractions such as Capitol Theatre, or get outdoors into nature at a spot like Rye Beach. While here, Clay Art Center Gallery and Capitol Theatre - Garcia’s are other places worth a visit.

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.