Port Chester Vacation Homes

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

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

In two months

In three months

In four months

Our top choices for Port Chester holiday homes

A dock with kayaks and a canoe, surrounded by trees and a calm lake.

1. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

Christopher J.

HK$2,686 total

includes taxes & fees

26 Oct - 27 Oct

An outdoor patio with a fire pit, green chairs, and a table.

2. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

New Rochelle

Drew C.

HK$2,606 total

includes taxes & fees

27 Oct - 28 Oct

A house with a porch, a white door, and a window with blinds.

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

Waterside

Leslie S.

HK$3,651 total

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

4. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Southeast Yonkers

Jordan S.

HK$1,057 total

includes taxes & fees

27 Oct - 28 Oct

A modern living room with a white sofa, a glass coffee table, and a piano.

5. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

West Side

Dave J.

HK$4,910 total

includes taxes & fees

28 Oct - 29 Oct

6. 5BR Beach House, Game Room + Huge Backyard

Cove - East Side - Shippan

Linda M.

HK$11,947 total

includes taxes & fees

31 Oct - 1 Nov

A living room with a sofa, armchair, ottoman, and coffee table.

7. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

HK$3,924 total

includes taxes & fees

26 Oct - 27 Oct

A modern living room with a blue rocking chair, a wooden coffee table, and a vase with dried plants. There are two framed artworks on the wall and a wooden accent wall.

8. Cozy Home.

Hempstead

Gina O.

HK$2,302 total

includes taxes & fees

26 Oct - 27 Oct

A room with two beds, white curtains, a ceiling light, and a window with a view.

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

White Plains

"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"

Ethan G.

HK$6,530 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

10. 5BR Beach House, Water Views, Steps to Beach, Backyard

Cove - East Side - Shippan

Maxx V.

HK$7,710 total

includes taxes & fees

1 Nov - 2 Nov

A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

11. Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor

Stacey S.

HK$3,943 total

includes taxes & fees

26 Oct - 27 Oct

A modern outdoor patio with a seating area, a central table, and a large umbrella.

12. Mansion in Greenwich with private lake and river

Greenwich

J.J. O.

HK$43,014 total

includes taxes & fees

14 Nov - 15 Nov

A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

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

Greenwich

Nathan R.

HK$24,320 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with a marble island, bar stools, and a built-in oven.

14. Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Huntington

Logan M.

HK$3,261 total

includes taxes & fees

26 Oct - 27 Oct

A modern living room with a glass coffee table, white sofa, and a staircase leading to an upper level.

15. Modern 3BR Home • Balcony • Free Parking • Near NYC

Southeast Yonkers

"Avoid booking with this host. We experienced a bait-and-switch situation where the original property could not be located, and the host attempted to move us to different properties that looked nothing like the listing and were in locations that felt unkept and unsafe, especially since we arrived at night.The host confirmed everything was fine until the very last minute, leaving us stranded upon arrival. They also communicated outside the VRBO platform using multiple phone numbers, then later...

Tatiana B.

16. Comfortable 3BR House • Free Parking • Easy NYC Access • Ideal for Fami...

Southeast Yonkers

HK$6,478 total

includes taxes & fees

30 Oct - 31 Oct

A modern kitchen with white cabinets, a marble island, and black bar stools.

17. Spacious Retreat with Game Room and Fire Pit

West Norwalk

Linda S.

HK$5,731 total

includes taxes & fees

28 Oct - 29 Oct

A modern living room with a sectional sofa, a glass coffee table, and a marble rug. There are two wall art pieces and a potted plant.

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

White Plains

"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...

James D.

HK$10,764 total

includes taxes & fees

26 Oct - 27 Oct

A living room with a sectional sofa, a white armchair, a patterned rug, and a wooden floor.

19. Stylish 3BR Near NYC • Free Parking • Perfect for Families & Groups

Southeast Yonkers

HK$7,684 total

includes taxes & fees

30 Oct - 31 Oct

A modern living room with a beige sectional sofa, a green armchair, a marble-patterned rug, a gold coffee table, and a flat-screen TV mounted on a white wall.

20. Luxury Single Family 3BR Home + Game Room and Parking

Bryn Mawr

CJ W.

HK$6,280 total

includes taxes & fees

1 Nov - 2 Nov

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Port Chester Hotel Reviews

Royal Regency Hotel

10/10 Excellent

"1 day stay, clean"

Hyatt Place Fort Lee / George Washington Bridge

10/10 Excellent

"⭐⭐⭐⭐⭐ I had a great experience staying at the Hyatt House in Fort Lee, New Jersey. The hotel was clean, comfortable, and well maintained. The staff were friendly, welcoming, and helpful throughout my stay. The room was spacious and comfortable, and the overall atmosphere was peaceful and relaxing. The location was convenient, making it easy to get around. Overall, I really enjoyed my stay and would definitely recommend this hotel to anyone visiting the Fort Lee area. I would be happy to stay here again!"

Find out more about Port Chester