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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Port Chester vacation 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, (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.
$344 nightly
The price is $393
Nov 15 - Nov 16
Total with taxes and fees
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
8.6 out of 10, Excellent, (7 reviews)
"Amazing host I appreciate everything she did for me"
United States
CSQUARED A.
$243 nightly
The price is $278
Nov 13 - Nov 14
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A rustic cabin surrounded by lush greenery and a stone pathway leading to it.

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.
$1,285 nightly
The price is $1,471
Nov 13 - Nov 14
Total with taxes and fees
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
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!
3.5 star property
Greenwich
$439 nightly
The price is $505
Nov 13 - Nov 14
Total with taxes and fees
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!
Greenwich
8.0 out of 10, Very good, (4 reviews)
"Price was right for the stay! I would come back"
United States
Mark
$408 nightly
The price is $467
Nov 13 - Nov 14
Total with taxes and fees
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

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
$149 nightly
The price is $171
Nov 22 - Nov 23
Total with taxes and fees
Stamford Suites
A forested area with a bench and a fire pit.

7. Historic, private riverfront cottage in peaceful Greenwich

Historic, private riverfront cottage in peaceful Greenwich
Greenwich
$320 nightly
The price is $364
Nov 19 - Nov 20
Total with taxes and fees
Historic, private riverfront cottage in peaceful Greenwich
An outdoor seating area with a round table, a chair, and a hanging light fixture.

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.
$390 nightly
The price is $445
Nov 16 - Nov 17
Total with taxes and fees
Gem by the water+ firepit and all fenced backyard
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

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.
$286 nightly
The price is $327
Nov 15 - Nov 16
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern living room with a white sofa, a glass coffee table, and a piano.

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.
$458 nightly
The price is $524
Nov 15 - Nov 16
Total with taxes and fees
Spacious 3BR Townhome | Garage + Near Downtown
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

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.
$336 nightly
The price is $385
Nov 15 - Nov 16
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

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.
$495 nightly
The price is $567
Nov 15 - Nov 16
Total with taxes and fees
Seabreeze at the beach west beach Stamford ct.
Living area

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.
$218 nightly
The price is $250
Nov 15 - Nov 16
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A modern living room with a dining area, a sofa, a TV, and a large window.

14. Cozy Modern Home Free Parking

Cozy Modern Home Free Parking
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
$241 nightly
The price is $274
Dec 1 - Dec 2
Total with taxes and fees
Cozy Modern Home Free Parking
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.

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.
$301 nightly
The price is $343
Nov 13 - Nov 14
Total with taxes and fees
Modern Luxury 1BR Stamford Getaway
A modern living room with a sofa, a coffee table, and a bar stool.

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.
$263 nightly
The price is $300
Nov 20 - Nov 21
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A modern living room with a grey sofa, a small round coffee table, and a dining area with a kitchen in the background.

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.
$256 nightly
The price is $291
Nov 23 - Nov 24
Total with taxes and fees
Romantic hideout. 1Br. Lower Level
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

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.
$1,952 nightly
The price is $2,222
Nov 16 - Nov 17
Total with taxes and fees
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A kitchenette with a water dispenser, microwave, coffee machine, and snack vending machine.

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 traveler
$123 nightly
The price is $140
Nov 24 - Nov 25
Total with taxes and fees
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.
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Top Port Chester Hotel Reviews

Four Points by Sheraton Flushing

Four Points by Sheraton Flushing

10/10 Excellent
"overall we’re happy with all amazing things"
Taslima 1-night trip
Posted 7 hours ago
Four Points by Sheraton Flushing

Find out more about Port Chester

Everything you need to know about Port Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Port Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Port Chester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Port Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $171 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Port Chester rentals

At Expedia, we put the best Port Chester vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Port Chester?

Yes, you can find vacation rentals in Port Chester close to Port Chester-Rye Brook Public Library, or you can select a secluded option if you're looking for extra privacy while you relax. Port Chester is known for its live music and entertainment choices. Make sure you have time to check out the theaters and waterfront during your trip.

What are some of the best vacation rentals that Port Chester has to offer?

Modern Luxury Home w GameRoom & Parking: You might want to consider this vacation rental near Port Chester, which 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 you can cook with friends or family.

How many vacation rentals will I find in Port Chester?

With 4 Expedia vacation rentals, you're sure 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 vacation rentals like in Port Chester?

Vacation rentals are privately owned properties you can book for a couple days or more in Port Chester. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips or small group gatherings.