Port Chester Holiday Rentals

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Check prices for these dates

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, (34 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$697
includes taxes & fees
15 Nov - 16 Nov
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
8.6 out of 10, Excellent, (7 reviews)
"Amazing host I appreciate everything she did for me"
United States
CSQUARED A.
The price is NZ$514
includes taxes & fees
13 Nov - 14 Nov
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

3. 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, (14 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is NZ$2,623
includes taxes & fees
13 Nov - 14 Nov
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

4. 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$901
includes taxes & fees
25 Nov - 26 Nov
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

5. 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$874
includes taxes & fees
21 Nov - 22 Nov
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!

6. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (208 reviews)
"Very limited breakfast…bagels and coffee…help your self. One plus small kitchenette"
United States
Christine
The price is NZ$308
includes taxes & fees
22 Nov - 23 Nov
Stamford Suites

7. Historic, private riverfront cottage in peaceful Greenwich

Historic, private riverfront cottage in peaceful Greenwich
Greenwich
The price is NZ$644
includes taxes & fees
18 Nov - 19 Nov
Historic, private riverfront cottage in peaceful Greenwich

8. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard
Waterside
10.0 out of 10, Exceptional, (22 reviews)
"Property was exactly what we needed for our stay"
United States
Christopher E.
The price is NZ$781
includes taxes & fees
16 Nov - 17 Nov
Gem by the water+ firepit and all fenced backyard

9. 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, (46 reviews)
"Nice stay"
United States
Christopher J.
The price is NZ$597
includes taxes & fees
24 Nov - 25 Nov
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

10. Spacious 3BR Townhome | Garage + Near Downtown

Spacious 3BR Townhome | Garage + Near Downtown
West Side
9.2 out of 10, Wonderful, (9 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$943
includes taxes & fees
15 Nov - 16 Nov
Spacious 3BR Townhome | Garage + Near Downtown

11. 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$691
includes taxes & fees
15 Nov - 16 Nov
Modern Luxe 1BR Apt in Downtown Stamford

12. Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is NZ$1,019
includes taxes & fees
15 Nov - 16 Nov
Seabreeze at the beach west beach Stamford ct.

13. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
The price is NZ$449
includes taxes & fees
15 Nov - 16 Nov
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

14. Cozy Modern Home Free Parking

Cozy Modern Home Free Parking
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
The price is NZ$488
includes taxes & fees
1 Dec - 2 Dec
Cozy Modern Home Free Parking

15. 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.
The price is NZ$610
includes taxes & fees
13 Nov - 14 Nov
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$530
includes taxes & fees
20 Nov - 21 Nov
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

17. Romantic hideout. 1Br. Lower Level

Romantic hideout. 1Br. Lower Level
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is NZ$510
includes taxes & fees
23 Nov - 24 Nov
Romantic hideout. 1Br. Lower Level

18. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich
10.0 out of 10, Exceptional, (2 reviews)
"Great location on the lake which the kids loved. The hosts were very friendly and easy to communicate with. The addition of the outdoor grill was a big plus and we enjoyed many afternoons out on the deck. We would stay again."
United States
Nathan R.
The price is NZ$3,901
includes taxes & fees
16 Nov - 17 Nov
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

19. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (2 reviews)
"Our rooms felt cozy enough for two people with decent privacy due to separate bathrooms nearby too.The location suited our plan moving between airport runs & visits close by malls perfectly."
United States
Anonymous traveller
The price is NZ$252
includes taxes & fees
24 Nov - 25 Nov
1 King 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.

Find holiday rentals that suit your style

Top Port Chester Hotel Reviews

Find out more about Port Chester

Everything you need to know about Port Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Port Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Port Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Port Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Port Chester. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Port Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Port Chester holiday rentals we have selected for you start as low as NZ$307 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Port Chester rentals

At Expedia, we put the best Port Chester holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Port Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Port Chester holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Port Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

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