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

Port Chester Holiday Rentals

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Port Chester holiday rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, 176, (176 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is S$232
includes taxes & fees
20 Sept - 21 Sept
Stamford Suites
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

2. 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 S$641
includes taxes & fees
30 Sept - 1 Oct
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

3. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, 42, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is S$313
includes taxes & fees
17 Sept - 18 Sept
Guesthouse at Norwalk Inn
A breakfast buffet with pastries, fruits, and a coffee station.

4. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, 1, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is S$1,459
includes taxes & fees
20 Sept - 21 Sept
3BR Prime Luxury NY - Free Parking
A dining table with a glass top, a vase with flowers, and a variety of pastries and fruits.

5. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is S$951
includes taxes & fees
16 Sept - 17 Sept
Prime Luxe 3-BR NYC - Free Parking
A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

6. 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, (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 S$906
includes taxes & fees
27 Sept - 28 Sept
Luxury NYC Home Game Room Free Parking
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

7. Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
2.0 out of 10, 1, (1 review)
"Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere."
United States
Kathleen
The price is S$798
includes taxes & fees
24 Sept - 25 Sept
Luxury NYC Home with Free Parking for 12
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden floor.

8. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
2.0 out of 10, 1, (1 review)
The price is S$448
includes taxes & fees
24 Sept - 25 Sept
Elegant Hideaway with Free Parking
A modern living room with a beige sectional sofa, a green armchair, a marble-patterned rug, a gold coffee table, and a flat-screen TV mounted on a white wall.

9. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
5.6 out of 10, 4, (4 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is S$589
includes taxes & fees
3 Oct - 4 Oct
Luxury 3BR Family Home Game Room Parking
A modern living room with a sofa, armchairs, a coffee table, and a dining area with a table and chairs.

10. Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is S$1,401
includes taxes & fees
19 Sept - 20 Sept
Two Wash
A modern living room with a stone wall, a flat-screen TV, a white sofa, and a kitchen area with a bar counter and chairs.

11. Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
2.0 out of 10, 2, (2 reviews)
"My experience did not match the listing. I was asked to make payment outside the platform and the check-in process was not clear. I would not recommend this property. ⸻ ⭐⭐ Balanced Review The property did not meet expectations. When I arrived, the check-in process was unclear and the home appeared to be partially occupied. I was also instructed to make a payment outside of Hotels.com instead of using the platform. This caused confusion and concern. I would suggest the listing be...
United States
Dianelly
The price is S$634
includes taxes & fees
19 Sept - 20 Sept
Luxe 1BR Oasis - Prime NY Stay
A modern living room with a sofa, armchairs, and a glass coffee table.

12. Luxury 5 BR Home Free Parking

Luxury 5 BR Home Free Parking
2.0 star property
Bryn Mawr
2.0 out of 10, 1, (1 review)
The price is S$1,018
includes taxes & fees
16 Sept - 17 Sept
Luxury 5 BR Home Free Parking
A modern living room with a white sofa, a glass coffee table, and a marble-patterned rug.

13. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.0 out of 10, 12, (12 reviews)
"Though the privous occupants refused to vacate the property in time but the landlord was suupportive went out of their way and provided a refund option and an alternative...we took the alternative which happen to be better than the originally booked property ... Will use this management and property owner in our upcoming short terms rentals....."
United States
abdelwahab
The price is S$1,039
includes taxes & fees
17 Sept - 18 Sept
Modern Luxury Home w GameRoom & Parking
A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

14. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
7.0 out of 10, 4, (4 reviews)
"My family and I were satisfy with the stay I’ll definitely coming back"
United States
Josephine
The price is S$763
includes taxes & fees
5 Oct - 6 Oct
Spacious 3BR Luxe Escape near NYC
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

15. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
9.0 out of 10, 2, (2 reviews)
"The house was very clean and the areas was quiet too. We had a nice spot to park the car. The staff was calling and checking on me if I didn’t have any issues with the check in. They were available all the time. The only thing we will need next time if possible is the washer and dryer and extra towels because we were 5 and only got 3 towels. But overall we enjoyed the stays."
United States
Adj Fatou
The price is S$648
includes taxes & fees
2 Oct - 3 Oct
Uscale 2BR Escape in the Heart of NYC
A two-story house with a front porch, a garage, and a well-maintained lawn.

16. Great Neck Basecamp: Steps to Downtown & Rail

Great Neck Basecamp: Steps to Downtown & Rail
3.0 star property
Great Neck
The price is S$635
includes taxes & fees
27 Sept - 28 Sept
Great Neck Basecamp: Steps to Downtown & Rail
A modern living room with a glass coffee table, teal sofa, and a television displaying a colorful scene.

17. Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is S$702
includes taxes & fees
11 Oct - 12 Oct
Luxury 3 BR Near NYC with Easy Parking
A modern kitchen with white cabinets, a central island with stools, a stone accent wall, a flat-screen TV, and a beige sofa with teal cushions.

18. Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
4.8 out of 10, 6, (6 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is S$647
includes taxes & fees
11 Oct - 12 Oct
Luxury 1BR located in Prime Yonkers Area
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

19. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is S$1,563
includes taxes & fees
16 Sept - 17 Sept
Summer Pool Oasis Custom Bar Arcade Pool Table
A modern kitchen with white cabinetry, a dining area with a glass table, and a view of the outdoors through large windows.

20. Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
3.6 out of 10, 4, (4 reviews)
"We never got to stay because THERE WAS ANOTHER FAMILY THERE. THAT WOMEN SAID SHE WAS RENTING THE HOUSE FOR ANOTHER MONTH. "
United States
Angel
The price is S$765
includes taxes & fees
11 Oct - 12 Oct
Modern Comfort in the Heart of NYC
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
"Stayed here for a 3-day trip in New York. The hotel was great. Room was clean, all the amenities were available, water pressure was excellent, TV channel selection was plenty. I didn't make it down for breakfast, but it's included, and they have a coffee bar available all day. The location was fine for my travel, but could be far for some people. Two subway stations are within minutes from the property. They have on-site parking, which was a necessity for me because I drove in to NY. It's $30/day for parking, which is reasonable, and you can exit/enter without additional fees."
Marvilla 2-night trip
Posted 4 hours 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 Port Chester-Rye Brook Public Library, 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?

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside of Port Chester is situated near the airport, and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms, as well as a kitchen with a full-sized fridge, a dishwasher and a stovetop, so that you can cook with friends or family.

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 Hawthorne Beach. While here, Capitol Theatre - Garcia’s and Port Chester-Rye Brook Public Library 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.