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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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.
$361 nightly
The price is $413
Oct 25 - Oct 26
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)
"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.
$266 nightly
The price is $301
Oct 21 - Oct 22
Total with taxes and fees
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
6.2 out of 10, (197 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$167 nightly
The price is $192
Oct 21 - Oct 22
Total with taxes and fees
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
$448 nightly
The price is $507
Oct 21 - Oct 22
Total with taxes and fees
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
Interior

5. 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.
$239 nightly
The price is $271
Oct 26 - Oct 27
Total with taxes and fees
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
A modern living room with a sofa, a coffee table, and a bar stool.

6. 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.
$277 nightly
The price is $314
Oct 26 - Oct 27
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

7. 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
Oct 21 - Oct 22
Total with taxes and fees
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A motel with a blue awning and a '6 Now Open' sign.

8. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
8.4 out of 10, Very good, (5 reviews)
$116 nightly
The price is $133
Oct 26 - Oct 27
Total with taxes and fees
1 Queen Bed | Non-Smoking
A rustic cabin surrounded by lush greenery and a stone pathway leading to it.

9. 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.
$1,418 nightly
The price is $1,604
Oct 21 - Oct 22
Total with taxes and fees
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

10. 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, (45 reviews)
"Nice stay"
United States
Christopher J.
$349 nightly
The price is $395
Oct 25 - Oct 26
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
An outdoor patio with a fire pit, green chairs, and a table.

11. 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, (12 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
United States
Drew C.
$309 nightly
The price is $353
Oct 27 - Oct 28
Total with taxes and fees
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

12. 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.
$115 nightly
The price is $135
Oct 21 - Oct 22
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A residential backyard with a lawn, a shed, and a house.

13. 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, (21 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
$411 nightly
The price is $466
Oct 25 - Oct 26
Total with taxes and fees
Gem by the water+ firepit and all fenced backyard
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

14. 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.
$368 nightly
The price is $417
Oct 25 - Oct 26
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
A modern gym with various weightlifting equipment, including a squat rack and kettlebells.

15. The Arches Suites

The Arches Suites
2.0 star property
Bronx
$206 nightly
The price is $240
Nov 12 - Nov 13
Total with taxes and fees
The Arches Suites
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.

16. 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.
$317 nightly
The price is $359
Oct 28 - Oct 29
Total with taxes and fees
Modern Luxury 1BR Stamford Getaway
A motel with a blue awning and a '6 Now Open' sign.

17. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"Beds were adequate, nothing special but perfectly fine for a short overnight stay."
United States
Anonymous traveler
$116 nightly
The price is $133
Oct 26 - Oct 27
Total with taxes and fees
1 Queen Bed | Smoking
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

18. 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
$119 nightly
The price is $136
Oct 26 - Oct 27
Total with taxes and fees
1 King Bed | Non-Smoking
A kitchenette with a water dispenser, microwave, coffee machine, and a snack vending machine.

19. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"The staff were attentive without being pushy, and the bed provided good comfort."
United States
Anonymous traveler
$122 nightly
The price is $140
Oct 26 - Oct 27
Total with taxes and fees
2 Full Beds | Non-Smoking
A garden with a stone wall, a wooden fence, and a gravel path.

20. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (23 reviews)
"Great place to stay! "
United States
Megan D.
$189 nightly
The price is $211
Nov 16 - Nov 17
Total with taxes and fees
Piermont Oasis
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

Executive Inn - Fort Lee

Executive Inn - Fort Lee

10/10 Excellent
"El personal muy amable y hablaba español que eso me súper encantó, hacían limpieza seguido y siempre fueron amables, el hotel sus habitaciones muy cómodas y limpias y los alrededores muy tranquilo todo. Si me volvería a hospedar en éste hotel por el precio y comodidad"
Jaishla 3-night trip
Posted less than an hour ago
Executive Inn - Fort Lee

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 $192 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.