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

Port Chester Holiday Rentals

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Our top choices for Port Chester holiday rentals

1. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
The price is NZ$708
includes taxes & fees
18 Aug - 19 Aug
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

2. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.0 out of 10, Very good, (5 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is NZ$417
includes taxes & fees
6 Sept - 7 Sept
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

3. 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 NZ$495
includes taxes & fees
23 Aug - 24 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

4. Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (9 reviews)
"This house is the perfect private getaway! Everything was just as described and the host was super helpful. Will definitely stay again. "
United States
Anna F.
The price is NZ$2,161
includes taxes & fees
23 Aug - 24 Aug
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

5. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is NZ$1,879
includes taxes & fees
15 Aug - 16 Aug
Prime Luxe 3-BR NYC - Free Parking

6. 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 NZ$1,075
includes taxes & fees
15 Aug - 16 Aug
Luxury NYC Home with Free Parking for 12

7. 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 NZ$1,965
includes taxes & fees
15 Aug - 16 Aug
3BR Prime Luxury NY - Free Parking

8. Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
White Plains
The price is NZ$860
includes taxes & fees
27 Aug - 28 Aug
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

9. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is NZ$678
includes taxes & fees
8 Sept - 9 Sept
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is NZ$604
includes taxes & fees
21 Aug - 22 Aug
Elegant Hideaway with Free Parking

11. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
The price is NZ$889
includes taxes & fees
16 Aug - 17 Aug
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

12. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is NZ$2,237
includes taxes & fees
15 Aug - 16 Aug
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

13. 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 NZ$1,220
includes taxes & fees
15 Aug - 16 Aug
Luxury NYC Home Game Room Free Parking

14. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
West Side
9.4 out of 10, Exceptional, (8 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is NZ$1,179
includes taxes & fees
14 Sept - 15 Sept
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

15. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is NZ$599
includes taxes & fees
16 Aug - 17 Aug
Modern Luxury 1BR Stamford Getaway

16. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is NZ$533
includes taxes & fees
16 Aug - 17 Aug
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

17. Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is NZ$708
includes taxes & fees
27 Aug - 28 Aug
Modern Luxe 1BR Apt in Downtown Stamford

18. Stylish Home With Free ParkingFA

Stylish Home With Free ParkingFA
Downtown Stamford
The price is NZ$503
includes taxes & fees
10 Sept - 11 Sept
Stylish Home With Free ParkingFA

19. Stylish Home and Cozy

Stylish Home and Cozy
Downtown Stamford
The price is NZ$1,044
includes taxes & fees
15 Aug - 16 Aug
Stylish Home and Cozy
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

Find out more about Port Chester

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Port Chester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Port Chester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Port Chester. Seeing all the best attractions is bound to make you fall in love with Port Chester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Port Chester short-term rentals, that won’t be hard to do.

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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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This holiday home rental outside of Port Chester is located next to a golf course, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as table football.

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 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.