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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Port Chester holiday rentals

A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

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 HK$1,726
HK$3,240 total
includes taxes & fees
18 Oct - 19 Oct
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
A wooden staircase leading to a gazebo in a forested area with a metal railing.

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 HK$1,765
HK$2,363 total
includes taxes & fees
4 Oct - 5 Oct
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

3. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (186 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is HK$1,146
HK$1,317 total
includes taxes & fees
12 Oct - 13 Oct
Stamford Suites
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

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 HK$2,119
HK$3,979 total
includes taxes & fees
9 Oct - 10 Oct
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

5. 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 HK$2,581
HK$3,962 total
includes taxes & fees
9 Oct - 10 Oct
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A campfire with a wooden table and benches by a lake.

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 HK$1,271
HK$2,443 total
includes taxes & fees
7 Oct - 8 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

7. 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 HK$1,285
HK$2,663 total
includes taxes & fees
8 Oct - 9 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A modern living room with a sofa, a coffee table, and a bar stool.

8. 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 HK$1,130
HK$2,468 total
includes taxes & fees
4 Oct - 5 Oct
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

9. 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 HK$1,130
HK$3,269 total
includes taxes & fees
8 Oct - 9 Oct
Modern Luxe 1BR Apt in Downtown Stamford
An outdoor patio with a fire pit, green chairs, and a table.

10. 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 HK$1,153
HK$2,755 total
includes taxes & fees
6 Oct - 7 Oct
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a sink. There are two bar stools at the counter.

11. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
8.0 out of 10, Very good, (2 reviews)
"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.
Modern Luxury 1BR Stamford Getaway
A modern kitchen with a central island, pendant lights, and built-in shelves.

12. Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
The price is HK$1,601
HK$2,347 total
includes taxes & fees
27 Oct - 28 Oct
Stylish Home and Cozy200
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

13. 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 HK$741
HK$1,058 total
includes taxes & fees
7 Oct - 8 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

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 HK$1,836
HK$4,356 total
includes taxes & fees
20 Oct - 21 Oct
Seabreeze at the beach west beach Stamford ct.
A spacious living room with a large sliding glass door leading to a patio, a cozy seating area with a sofa and armchairs, and a modern art piece on the wall.

15. Solara – Luxury 1BR Downtown

Solara – Luxury 1BR Downtown
Downtown Stamford
The price is HK$1,649
HK$3,332 total
includes taxes & fees
15 Oct - 16 Oct
Solara – Luxury 1BR Downtown
A hotel room with a bed, a desk, a chair, a TV, and a window with a curtain.

16. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
The price is HK$1,045
HK$1,195 total
includes taxes & fees
4 Oct - 5 Oct
1 Queen Bed | Smoking
A stone staircase leading up to a house, surrounded by greenery and a blue tarp.

17. Garden Loft with Patios & Green Space · Westchester Retreat

Garden Loft with Patios & Green Space · Westchester Retreat
Scarsdale
9.0 out of 10, Wonderful, (6 reviews)
"It was excellent!! "
United States
Henry C.
The price is HK$1,711
HK$3,015 total
includes taxes & fees
11 Oct - 12 Oct
Garden Loft with Patios & Green Space · Westchester Retreat
A modern living room with a white sofa, a glass coffee table, and a piano.

18. 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 HK$2,778
HK$5,254 total
includes taxes & fees
27 Oct - 28 Oct
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A dining table with a variety of pastries and fruits, a vase with flowers, and a view of a brick wall and greenery outside.

19. 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, (2 reviews)
"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 HK$3,178
HK$4,944 total
includes taxes & fees
6 Oct - 7 Oct
Luxury NYC Home with Free Parking for 12
A rustic cabin surrounded by lush greenery and a stone pathway leading to it.

20. 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 HK$7,023
HK$13,484 total
includes taxes & fees
18 Oct - 19 Oct
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to 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

The Parc Hotel

The Parc Hotel

10/10 Excellent
"Good experience, comfortable stay, perfect location, rooftop bar"
Nasir 2-night trip
Posted 2 hours ago
The Parc Hotel

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 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.