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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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, (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.
$341 nightly
The price is $390
Oct 4 - Oct 5
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
8.0 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.
$252 nightly
The price is $287
Oct 3 - Oct 4
Total with taxes and fees
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

3. 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
Sep 30 - Oct 1
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.

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
$420 nightly
The price is $479
Sep 30 - Oct 1
Total with taxes and fees
2 Mi to NYC Train: WFH-Friendly Greenwich Apt!
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

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.
$278 nightly
The price is $316
Sep 30 - Oct 1
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
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.
$262 nightly
The price is $298
Oct 5 - Oct 6
Total with taxes and fees
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

7. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (184 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
$154 nightly
The price is $178
Sep 30 - Oct 1
Total with taxes and fees
Stamford Suites
An outdoor patio with a fire pit, green chairs, and a table.

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.
$291 nightly
The price is $333
Sep 29 - Sep 30
Total with taxes and fees
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
A modern living room with a sofa, a coffee table, and a bar stool.

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.
$264 nightly
The price is $301
Oct 4 - Oct 5
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

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.
$115 nightly
The price is $135
Sep 27 - Sep 28
Total with taxes and fees
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A hotel room with a bed, a desk, a chair, a TV, and a window with a curtain.

11. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
$118 nightly
The price is $135
Sep 29 - Sep 30
Total with taxes and fees
1 Queen Bed | Smoking
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

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.
$348 nightly
The price is $397
Sep 27 - Sep 28
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford
A rustic cabin surrounded by lush greenery and a stone pathway leading to it.

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.
$1,337 nightly
The price is $1,523
Sep 27 - Sep 28
Total with taxes and fees
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
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.
$457 nightly
The price is $521
Sep 29 - Sep 30
Total with taxes and fees
Seabreeze at the beach west beach Stamford ct.
A bedroom with a bed, dresser, and a ceiling fan.

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
$181 nightly
The price is $213
Oct 4 - Oct 5
Total with taxes and fees
Cozy 1-bedroom apartment in lovely Yonkers minutes from Empire Casino and NYC
A modern kitchen with a central island, pendant lights, and built-in shelves.

16. Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
$230 nightly
The price is $262
Sep 27 - Sep 28
Total with taxes and fees
Stylish Home and Cozy200
A garden with a stone wall, a wooden fence, and a gravel path.

17. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (21 reviews)
"Great place to stay! "
United States
Megan D.
$185 nightly
The price is $206
Oct 27 - Oct 28
Total with taxes and fees
Piermont Oasis
A modern kitchen with stainless steel appliances, a central island with chairs, and a window with a view.

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
$449 nightly
The price is $514
Sep 27 - Sep 28
Total with taxes and fees
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

19. Charming 2-bedroom Apartment with AC in Yonkers

Charming 2-bedroom Apartment with AC in Yonkers
Bryn Mawr
$330 nightly
The price is $388
Sep 27 - Sep 28
Total with taxes and fees
Charming 2-bedroom Apartment with AC in Yonkers
A motel with a blue awning and a '6 Now Open' sign.

20. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
$118 nightly
The price is $135
Sep 29 - Sep 30
Total with taxes and fees
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

Highbridge Hotel

Highbridge Hotel

10/10 Excellent
"Enjoyed my first stay at this hotel. Room was clean and well maintained. The modern bathroom was a nice surprise. Enjoyed the complimentary breakfast. The parking area was convenient and secure."
Jimmy 1-night trip
Posted 1 hour ago
Highbridge Hotel

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 $178 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.