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

Port Chester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Port Chester vacation rentals

Apartment (1 Bedroom) | Interior

1. 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 ￥22,351
￥45,632 total
includes taxes & fees
Aug 3 - Aug 4
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Exterior

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (149 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is ￥19,910
￥22,896 total
includes taxes & fees
Aug 11 - Aug 12
Stamford Suites
Luxury Apartment | Private kitchen

3. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is ￥28,191
￥55,695 total
includes taxes & fees
Aug 2 - Aug 3
Elegant Hideaway with Free Parking
Luxury Apartment | Living area

4. 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 ￥17,140
￥42,628 total
includes taxes & fees
Aug 7 - Aug 8
NY Luxury Apt Free Parking in PRIME Area
Luxury Villa, Garden View | Dining

5. 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 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 ￥63,747
￥99,174 total
includes taxes & fees
Aug 3 - Aug 4
Luxury NYC Home with Free Parking for 12
Standard Room, 1 King Bed, Main Building | Property entrance

6. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is ￥56,507
￥64,983 total
includes taxes & fees
Aug 2 - Aug 3
Guesthouse at Norwalk Inn
Villa, Garden View | Living area

7. 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 ￥77,913
￥112,564 total
includes taxes & fees
Aug 8 - Aug 9
Luxury NYC Home Game Room Free Parking
Dining

8. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is ￥92,079
￥126,006 total
includes taxes & fees
Aug 2 - Aug 3
Prime Luxe 3-BR NYC - Free Parking
Luxury Apartment | Living area

9. 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 ￥56,980
￥87,200 total
includes taxes & fees
Aug 2 - Aug 3
Luxury 3 BR Near NYC with Easy Parking
Luxury Duplex | Living area

10. Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
8.0 out of 10, Very Good, (1 review)
"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 ￥49,440
￥80,338 total
includes taxes & fees
Aug 2 - Aug 3
Uscale 2BR Escape in the Heart of NYC
Apartment (4 Bedrooms) | Interior

11. Walkable Neighborhood! Long Island Basecamp

Walkable Neighborhood! Long Island Basecamp
3.0 star property
Great Neck
The price is ￥31,323
￥72,578 total
includes taxes & fees
Sep 1 - Sep 2
Walkable Neighborhood! Long Island Basecamp
Luxury House | Living area

12. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very Good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is ￥63,747
￥94,769 total
includes taxes & fees
Aug 7 - Aug 8
Spacious 3BR Luxe Escape near NYC
Front of property - evening/night

13. Global Luxury Suites at The Arches

Global Luxury Suites at The Arches
2.5 star property
Bronx
6.8 out of 10, (613 reviews)
"It was a great stay easy check in. It wasn’t the cleanest and we ran out of towels. The balcony view was amazing though."
United States
Daniel
The price is ￥15,525
￥32,636 total
includes taxes & fees
Aug 5 - Aug 6
Global Luxury Suites at The Arches
Luxury House, Garden View | Living area

14. Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
6.8 out of 10, (3 reviews)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is ￥44,495
￥73,231 total
includes taxes & fees
Aug 3 - Aug 4
Luxury 3BR Family Home Game Room Parking
Luxury Apartment | In-room dining

15. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (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 ￥141,660
￥181,226 total
includes taxes & fees
Aug 4 - Aug 5
3BR Prime Luxury NY - Free Parking
Luxury Apartment | Living area

16. 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 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is ￥50,856
￥80,348 total
includes taxes & fees
Aug 2 - Aug 3
Luxury 1BR located in Prime Yonkers Area
Luxury Apartment | Living area

17. Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
2.0 out of 10, (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 ￥49,440
￥78,765 total
includes taxes & fees
Aug 20 - Aug 21
Luxe 1BR Oasis - Prime NY Stay
Luxury House | Living area

18. Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
2.0 out of 10, (1 review)
"Very inaccurate listing upon arriving host called me stating I could not stay at property due to issues on their end instead of offering a refund I was sent to a different property that was a 1 bedroom with 1 bed that was clearly not cleaned instead of the 3 bedroom 5 bed luxury house I initially booked I explained this would not work for me and my 4 other guests and got told there was no other choice and hung up on, me and my guests had no option beside to go back home very bad experience DO...
United States
Gerald
The price is ￥63,747
￥94,769 total
includes taxes & fees
Aug 7 - Aug 8
Spacious 3BR Luxe Escape near NYC
House | Living area

19. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
5.2 out of 10, (9 reviews)
"Don’t stay here. Not as listed. "
United States
Kenyon
The price is ￥102,310
￥137,912 total
includes taxes & fees
Aug 2 - Aug 3
Modern Luxury Home w GameRoom & Parking
Luxury House, Garden View | Dining

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 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 ￥92,079
￥126,465 total
includes taxes & fees
Aug 4 - Aug 5
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Port Chester Hotel Reviews

The Westin Flushing Laguardia Airport

The Westin Flushing Laguardia Airport

10/10 Excellent
"Better than expected. No complaints the rooms were clean and updated....fancy"
LaToria 4-night trip
Posted 3 hours ago
The Westin Flushing Laguardia Airport

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 vacation rental in Port Chester?

Yes, you can find vacation rentals in Port Chester close to Clay Art Center Gallery, or you can select a secluded option if you're looking for extra privacy while you relax. Port Chester is known for its live music and entertainment choices. Make sure you have time to check out the theaters and waterfront during your trip.

What are some of the best vacation rentals that Port Chester has to offer?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: Visitors like this Port Chester vacation home rental. It is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals will I find in Port Chester?

With 4 Expedia vacation rentals, you're sure 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 vacation rentals like in Port Chester?

Vacation rentals are privately owned properties you can book for a couple days or more in Port Chester. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.