A suspension bridge over a calm river, surrounded by hills and autumn foliage.

Port Chester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Port Chester vacation rentals

TV

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 AED 808
AED 1,529 total
includes taxes & fees
11 Aug - 12 Aug
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Property grounds

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
7.6 out of 10, Good, (4 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 AED 403
AED 567 total
includes taxes & fees
11 Aug - 12 Aug
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Apartment (1 Bedroom) | Interior

3. 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 AED 522
AED 1,065 total
includes taxes & fees
11 Aug - 12 Aug
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
Property grounds

4. 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, (9 reviews)
"This house is the perfect private getaway! Everything was just as described and the host was super helpful. Will definitely stay again. "
United States
Anna F.
The price is AED 1,967
AED 4,603 total
includes taxes & fees
13 Aug - 14 Aug
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Dining

5. Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is AED 3,140
AED 4,045 total
includes taxes & fees
11 Aug - 12 Aug
Prime Luxe 3-BR NYC - Free Parking
Luxury Villa, Garden View | Dining

6. 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, (1 review)
"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 AED 1,488
AED 2,314 total
includes taxes & fees
11 Aug - 12 Aug
Luxury NYC Home with Free Parking for 12
Luxury Apartment | In-room dining

7. 3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is AED 3,306
AED 4,229 total
includes taxes & fees
11 Aug - 12 Aug
3BR Prime Luxury NY - Free Parking
Private kitchen

8. Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC

Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
White Plains
The price is AED 1,818
AED 3,054 total
includes taxes & fees
11 Aug - 12 Aug
Family-Friendly 3BR Home • Game Room • Free Parking • Minutes from NYC
Property grounds

9. 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, (18 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AED 782
AED 1,487 total
includes taxes & fees
8 Sep - 9 Sep
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Luxury Apartment | Private kitchen

10. Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is AED 658
AED 1,300 total
includes taxes & fees
14 Aug - 15 Aug
Elegant Hideaway with Free Parking
3 bedrooms, iron/ironing board, internet, bed sheets

11. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
White Plains
The price is AED 1,818
AED 3,067 total
includes taxes & fees
11 Aug - 12 Aug
Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups
Smart TV

12. Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is AED 1,980
AED 3,307 total
includes taxes & fees
13 Aug - 14 Aug
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
Living area

13. Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC

Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
White Plains
2.0 out of 10, (1 review)
"An hour before check-in we were called by the property manager, after four days of messaging them through the app without response, to advise us that the property had an alleged water pipe burst and was unavailable, then attempted to upcharge us for alternate accommodations. An alternate place to stay was finally provided at no additional charge but much smaller than what had been booked. Given the absence of communication for four days and then a sudden incident the day of check-in - the day...
United States
James D.
The price is AED 3,306
AED 5,041 total
includes taxes & fees
11 Aug - 12 Aug
Spacious Luxury Retreat Sleeps 16 • Prime Area • Free Parking • Near NYC
Villa, Garden View | Living area

14. Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is AED 1,818
AED 2,627 total
includes taxes & fees
11 Aug - 12 Aug
Luxury NYC Home Game Room Free Parking
Interior

15. Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
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 AED 1,649
AED 2,888 total
includes taxes & fees
17 Aug - 18 Aug
Walkable Townhouse with Garage & Yard, 45 min to NYC!
Private kitchen

16. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
"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 AED 731
AED 1,311 total
includes taxes & fees
13 Aug - 14 Aug
Modern Luxury 1BR Stamford Getaway
Offices

17. 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 AED 529
AED 1,145 total
includes taxes & fees
13 Aug - 14 Aug
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Smart TV

18. 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 AED 529
AED 1,534 total
includes taxes & fees
19 Aug - 20 Aug
Modern Luxe 1BR Apt in Downtown Stamford
Coffee/tea maker, fridge, microwave, oven

19. Stylish Home With Free ParkingFA

Stylish Home With Free ParkingFA
Downtown Stamford
The price is AED 786
AED 1,159 total
includes taxes & fees
9 Sep - 10 Sep
Stylish Home With Free ParkingFA
Coffee/tea maker, fridge, microwave, oven

20. Stylish Home and Cozy

Stylish Home and Cozy
Downtown Stamford
The price is AED 1,646
AED 2,261 total
includes taxes & fees
23 Aug - 24 Aug
Stylish Home and Cozy
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Port Chester Hotel Reviews

Opera House Hotel

Opera House Hotel

10/10 Excellent
"The property was well kept hidden gym. The staff was most accommodating. The pillows could have been a little fluffier but did not, in any way, disrupt an amazing day. I would stay again."
Regina 3-night trip
Posted 1 hour ago
Opera House Hotel

Frequently asked questions

Can I find a vacation rental in Port Chester?

Yes, you can find vacation rentals in Port Chester close to Clay Art Center Gallery, 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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: Visitors like this Port Chester vacation home rental. It is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

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 Rye Beach. While here, Capitol Theatre - Garcia’s and Clay Art Center Gallery 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.