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$727
includes taxes & fees
27 Oct - 28 Oct
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$525
includes taxes & fees
4 Oct - 5 Oct
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$892
includes taxes & fees
30 Sept - 1 Oct
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

4. 2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Greenwich
8.0 out of 10, Very good, (4 reviews)
"Price was right for the stay! I would come back"
United States
Mark
The price is NZ$890
includes taxes & fees
30 Sept - 1 Oct
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

5. 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, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is NZ$572
includes taxes & fees
30 Sept - 1 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

6. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$544
includes taxes & fees
7 Oct - 8 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

7. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (185 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is NZ$314
includes taxes & fees
30 Sept - 1 Oct
Stamford Suites

8. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Rochelle
10.0 out of 10, Exceptional, (11 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
The price is NZ$606
includes taxes & fees
30 Sept - 1 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

9. 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$548
includes taxes & fees
12 Oct - 13 Oct
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

10. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is NZ$238
includes taxes & fees
4 Oct - 5 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

11. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
The price is NZ$238
includes taxes & fees
29 Sept - 30 Sept
1 Queen Bed | Smoking

12. 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$732
includes taxes & fees
2 Oct - 3 Oct
Modern Luxe 1BR Apt in Downtown Stamford

13. 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, (13 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is NZ$2,937
includes taxes & fees
18 Oct - 19 Oct
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

14. Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (17 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is NZ$1,038
includes taxes & fees
29 Oct - 30 Oct
Seabreeze at the beach west beach Stamford ct.

15. Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC

Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC
Dunwoodie
The price is NZ$375
includes taxes & fees
4 Oct - 5 Oct
Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC

16. Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
The price is NZ$533
includes taxes & fees
30 Sept - 1 Oct
Stylish Home and Cozy200

17. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
The price is NZ$364
includes taxes & fees
27 Oct - 28 Oct
Piermont Oasis

18. 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$959
includes taxes & fees
29 Sept - 30 Sept
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

19. Charming 2-bedroom Apartment with AC in Yonkers

Charming 2-bedroom Apartment with AC in Yonkers
Bryn Mawr
The price is NZ$723
includes taxes & fees
29 Sept - 30 Sept
Charming 2-bedroom Apartment with AC in Yonkers

20. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
The price is NZ$238
includes taxes & fees
29 Sept - 30 Sept
1 Queen Bed | Non-Smoking
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?

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.