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

Port Chester Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Port Chester holiday rentals

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 RM582
RM1,187 total
includes taxes & fees
18 Aug - 19 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Exterior

2. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (152 reviews)
"The front desk gentleman that checked us in was excellent!!"
United States
Selena
The price is RM577
RM663 total
includes taxes & fees
16 Aug - 17 Aug
Stamford Suites
Private kitchen

3. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is RM734
RM1,449 total
includes taxes & fees
10 Aug - 11 Aug
Elegant Hideaway with Free Parking
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 RM446
RM1,109 total
includes taxes & fees
8 Aug - 9 Aug
NY Luxury Apt Free Parking in PRIME Area
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 RM1,659
RM2,580 total
includes taxes & fees
13 Aug - 14 Aug
Luxury NYC Home with Free Parking for 12
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 RM1,470
RM1,691 total
includes taxes & fees
10 Aug - 11 Aug
Guesthouse at Norwalk Inn
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 RM2,027
RM2,929 total
includes taxes & fees
7 Aug - 8 Aug
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 RM3,502
RM4,510 total
includes taxes & fees
7 Aug - 8 Aug
Prime Luxe 3-BR NYC - Free Parking
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 RM1,483
RM2,269 total
includes taxes & fees
18 Aug - 19 Aug
Luxury 3 BR Near NYC with Easy Parking
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 RM1,286
RM2,090 total
includes taxes & fees
18 Aug - 19 Aug
Uscale 2BR Escape in the Heart of NYC
Interior

11. Walkable Neighborhood! Long Island Basecamp

Walkable Neighborhood! Long Island Basecamp
3.0 star property
Great Neck
The price is RM762
RM1,829 total
includes taxes & fees
18 Aug - 19 Aug
Walkable Neighborhood! Long Island Basecamp
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 RM1,659
RM2,466 total
includes taxes & fees
18 Aug - 19 Aug
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, (614 reviews)
"everything was fine"
United States
kato
The price is RM461
RM915 total
includes taxes & fees
6 Aug - 7 Aug
Global Luxury Suites at The Arches
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 RM1,158
RM1,905 total
includes taxes & fees
18 Aug - 19 Aug
Luxury 3BR Family Home Game Room Parking
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 RM3,686
RM4,715 total
includes taxes & fees
6 Aug - 7 Aug
3BR Prime Luxury NY - Free Parking
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 RM1,323
RM2,091 total
includes taxes & fees
18 Aug - 19 Aug
Luxury 1BR located in Prime Yonkers Area
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 RM1,286
RM2,049 total
includes taxes & fees
21 Aug - 22 Aug
Luxe 1BR Oasis - Prime NY Stay
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 RM1,659
RM2,466 total
includes taxes & fees
11 Aug - 12 Aug
Spacious 3BR Luxe Escape near NYC
Living area

19. Modern Luxury Home w GameRoom & Parking

Modern Luxury Home w GameRoom & Parking
3.5 star property
Southeast Yonkers
4.8 out of 10, (10 reviews)
"Don’t stay here. Not as listed. "
United States
Kenyon
The price is RM2,662
RM3,588 total
includes taxes & fees
6 Aug - 7 Aug
Modern Luxury Home w GameRoom & Parking
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 RM2,396
RM3,291 total
includes taxes & fees
6 Aug - 7 Aug
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

Wingate by Wyndham Bronx/Haven Park

Wingate by Wyndham Bronx/Haven Park

8/10 Good
"The staff were extremely friendly and helpful! The rooms were very clean."
Staci 1-night trip
Posted less than an hour ago
Wingate by Wyndham Bronx/Haven Park

Find out more about Port Chester

Search for holiday rentals in Port Chester on Expedia.co.uk! 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 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, Capitol Theatre - Garcia’s and Clay Art Center Gallery 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.