Search Vacation Homes in Port Chester

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Port Chester vacation homes

Fridge, microwave, oven, stovetop
House in quiet Westchester county neighborhood

Vacation Home in Port Chester

2.0 star property
House in quiet Westchester county neighborhood
Property grounds
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Vacation Home in Greenwich

9.6 out of 10, Exceptional, (23)
"The property was beautiful and clean, very comfortable with a nice view of the lake! Our hosts were helpful and attentive without being intrusive in any way. Our stay was peaceful and restful, just perfect. "
United States
Victoria R.
The price is AED 471
AED 979 total
includes taxes & fees
11 Dec - 12 Dec
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Terrace/patio
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Vacation Home in Southeast Yonkers

8.2 out of 10, Very Good, (18)
"Great place great location"
United States
Daquan H.
The price is AED 347
AED 495 total
includes taxes & fees
14 Dec - 15 Dec
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Smart TV, fireplace, table tennis, computer monitors
Captain's Cottage - Cold Spring Harbor Water Views

Vacation Home in Cold Spring Harbor

10.0 out of 10, Exceptional, (73)
"Location was perfect!"
United States
Linda J P.
The price is AED 1,083
AED 2,161 total
includes taxes & fees
5 Jan - 6 January 2026
Captain's Cottage - Cold Spring Harbor Water Views
Property grounds
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Vacation Home in Waterside

9.8 out of 10, Exceptional, (9)
"Lovely little home in Stamford."
United States
Pat A.
The price is AED 578
AED 1,209 total
includes taxes & fees
14 Dec - 15 Dec
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Outdoor dining
45 Minutes from NYC, Entire House near Stamford Downtown,

Vacation Home in Downtown Stamford

10.0 out of 10, Exceptional, (20)
"Our hosts were very attentive and responsive with communications. The house is lovely, clean, well stocked and in a great location. We thoroughly enjoyed our stay!"
United States
Megan P.
The price is AED 606
AED 1,382 total
includes taxes & fees
17 Dec - 18 Dec
45 Minutes from NYC, Entire House near Stamford Downtown,
Private kitchen
Spacious Family Loft with Dining, Game Room, Near NYC, Sleeps 14

Vacation Home in Leonia

2.0 star property
The price is AED 658
AED 1,615 total
includes taxes & fees
16 Dec - 17 Dec
Spacious Family Loft with Dining, Game Room, Near NYC, Sleeps 14
Fridge, microwave, oven, stovetop
Spacious 4-bedroom 2.5 bath colonial in Hicksville by Seema

Vacation Home in Hicksville

10.0 out of 10, Exceptional, (1)
"Wonderful house for our family trip to Long Island, the perfect space for us and plenty of room for my littles to play. Rooms were spacious and comfortable and the house was clean! "
United States
Abigail F.
The price is AED 881
AED 1,570 total
includes taxes & fees
10 Dec - 11 Dec
Spacious 4-bedroom 2.5 bath colonial in Hicksville by Seema
Exterior
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Vacation Home in Norwalk

2.0 star property
10.0 out of 10, Exceptional, (8)
"We were so pleased with the accommodations. The location is so quiet in a charming neighborhood. The home is well equipped with kitchen supplied and entertainment options. We were delighted to be able to barbecue. Claudia is very responsive and helpful."
Canada
nawab k.
The price is AED 981
AED 2,183 total
includes taxes & fees
5 Jan - 6 January 2026
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC
Marina
Stylish Beach Home near Stamford Downtown/Beach

Vacation Home in Cove - East Side - Shippan

10.0 out of 10, Exceptional, (23)
"A very nice house, with excellent service and an unbeatable location. We had a great time."
Mexico
Armando V.
The price is AED 1,098
AED 2,676 total
includes taxes & fees
11 Dec - 12 Dec
Stylish Beach Home near Stamford Downtown/Beach
Property grounds
Charming 3-bedroom modern family retreat!

Vacation Home in Huntington

9.6 out of 10, Exceptional, (8)
"Great location & thoughtful amenities."
United States
Joshua
The price is AED 1,207
AED 1,802 total
includes taxes & fees
10 Dec - 11 Dec
Charming 3-bedroom modern family retreat!
Outdoor dining
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

Vacation Home in West Side

9.4 out of 10, Exceptional, (6)
"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 1,021
AED 2,052 total
includes taxes & fees
15 Dec - 16 Dec
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...
Property grounds
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Vacation Home in North Stamford

10.0 out of 10, Exceptional, (105)
"Wonderful family home!Everything you need!Beautiful location!Great host!"
United States
Linda T.
The price is AED 1,603
AED 3,456 total
includes taxes & fees
14 Dec - 15 Dec
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Luxury House | Private kitchen | Full-size fridge, microwave, oven, stovetop
Luxury NY Home with Free Parking

Vacation Home in White Plains

4.0 star property
8.0 out of 10, Very Good, (1)
"Rooms were very clean, well decorated however bathrooms were not. Parking was accessible and perfect. Some appliances did not work like iron stained my clothes and coffee machine did not work. Everything else was fine. "
United States
Safiya
The price is AED 1,226
AED 1,766 total
includes taxes & fees
10 Dec - 11 Dec
Luxury NY Home with Free Parking
Fridge, stovetop, dishwasher, coffee/tea maker
Cozy 2BR | Manhattan | 20 min to Times Square

Vacation Home in Manhattan

7.4 out of 10, Good, (3)
"Great place to stay and excellent communication with owner. Close to subway station and local restaurants and grocery store. Would stay again."
Canada
Kelly E.
The price is AED 1,136
AED 1,988 total
includes taxes & fees
23 Dec - 24 Dec
Cozy 2BR | Manhattan | 20 min to Times Square
Exterior
Cheerful Home in Yonkers NY

Vacation Home in Lincoln Park

7.6 out of 10, Good, (4)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
United States
Tanya J.
The price is AED 918
AED 2,119 total
includes taxes & fees
31 Dec - 1 January 2026
Cheerful Home in Yonkers NY
House | 5 bedrooms
Foliage at Westchester Manor - Near Sleepy Hollow

Vacation Home in Ossining

2.0 star property
The price is AED 1,516
AED 3,422 total
includes taxes & fees
5 Jan - 6 January 2026
Foliage at Westchester Manor - Near Sleepy Hollow
TV
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Vacation Home in Cove - East Side - Shippan

9.4 out of 10, Exceptional, (3)
"We chose to stay here for a family event nearby. We found the property very clean and comfortable throughout our stay and would not hesitate to book it again. Although this trip wasn’t about adventuring elsewhere, we know it is convenient to many great places in Fairfield County, Connecticut, as well as New York."
United States
Ellen L.
The price is AED 904
AED 1,898 total
includes taxes & fees
14 Dec - 15 Dec
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Interior
Luxury 6BR House with Pool & Outdoor BBQ

Vacation Home in Old Bethpage

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. It was for work so we didn’t have much time to enjoy ourselves other than to rest when we could. I would love to book it again. "
United States
Matthew P.
The price is AED 3,471
AED 6,045 total
includes taxes & fees
19 Dec - 20 Dec
Luxury 6BR House with Pool & Outdoor BBQ
Property grounds
Family Home near NY Beach, Private Workspace by Zen Living

Vacation Home in Glen Head

8.6 out of 10, Excellent, (7)
"Property was clean and had everything we needed for a quick weekend trip. Host was super quick to respond and checked in. "
United States
Jenna G.
The price is AED 1,366
AED 2,554 total
includes taxes & fees
27 Dec - 28 Dec
Family Home near NY Beach, Private Workspace by Zen Living
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

Hampton Inn New York - LaGuardia Airport

Hampton Inn New York - LaGuardia Airport

10/10 Excellent
"Yes, fast check in and 2 complimentary bottle water for us "
AMY 2-night trip
Posted 1 day ago
Hampton Inn New York - LaGuardia Airport