Port Chester Vacation Homes

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

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Our top choices for Port Chester holiday homes

A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

1. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

Leslie S.

HK$2,551 total

includes taxes & fees

13 Oct - 14 Oct

A campfire with a wooden table and benches by a lake.

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

Greenwich

Christopher J.

HK$2,647 total

includes taxes & fees

7 Oct - 8 Oct

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

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

New Rochelle

Drew C.

HK$2,738 total

includes taxes & fees

7 Oct - 8 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$1,058 total

includes taxes & fees

12 Oct - 13 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$5,122 total

includes taxes & fees

28 Oct - 29 Oct

A room with a wooden door, a small table with a vase, and a chair.

6. Spacious 3b/3b Mediterranean in White Plains

White Plains

Nancy K.

7. 5BR Beach House, Game Room + Huge Backyard

Cove - East Side - Shippan

Linda M.

HK$7,553 total

includes taxes & fees

7 Oct - 8 Oct

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

8. 5BR Beach Home | Walk to Cove Beach + Private Yard

Cove - East Side - Shippan

Maury A.

HK$5,681 total

includes taxes & fees

7 Oct - 8 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$6,552 total

includes taxes & fees

7 Oct - 8 Oct

A living room with a sofa set, a coffee table, and a television on a stand.

10. Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

james w.

HK$4,531 total

includes taxes & fees

7 Oct - 8 Oct

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

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

Greenwich

Nathan R.

HK$20,096 total

includes taxes & fees

7 Oct - 8 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.

12. Cozy Home.

Hempstead

Gina O.

HK$2,129 total

includes taxes & fees

12 Oct - 13 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.

13. 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$10,761 total

includes taxes & fees

7 Oct - 8 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.

14. 5BR Beach House, Water Views, Steps to Beach, Backyard

Cove - East Side - Shippan

Heather G.

HK$7,703 total

includes taxes & fees

8 Oct - 9 Oct

A two-story house with a large front porch, a garage, and a well-maintained lawn.

15. The Victorian Blue 25min to NYC

North Side

Sarah D.

HK$8,078 total

includes taxes & fees

12 Oct - 13 Oct

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

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

Huntington

Logan M.

HK$3,586 total

includes taxes & fees

7 Oct - 8 Oct

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

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

Cold Spring Harbor

Stacey S.

HK$4,411 total

includes taxes & fees

20 Oct - 21 Oct

A bedroom with a bed, a nightstand, a lamp, a mirror, a window with curtains, and a framed picture on the wall.

18. Gilded Age Luxury Surrounded by Nature

Cranbury

HK$3,367 total

includes taxes & fees

12 Oct - 13 Oct

A living room with a sofa, a coffee table, a wicker chair, a ceiling fan, and a large window with a view of a parked car outside.

19. Huntington Village House 4BR – Walk to everything

Huntington

Corinne J.

HK$6,321 total

includes taxes & fees

19 Oct - 20 Oct

A wooden staircase with a chandelier, leading to an upper floor. A stone wall and a flower arrangement are visible on the left.

20. 6 BR, 4 BA Mansion Close to the City

Getty Square

Megan T.

HK$7,032 total

includes taxes & fees

7 Oct - 8 Oct

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Top Port Chester Hotel Reviews

Inn at Jericho

8/10 Good

"Staff helpful & cheerful. Room could use a bit updating, but had a fridge & microwave. Bed good. Bath nicely updated with tile & decor. Small, price worthy & accessible."

Executive Inn - Fort Lee

10/10 Excellent

"Everything is exceptionally well, with the exception of the elevator, you have to wait forever to get the elevator, and when you get on the elevator, you still gotta wait along time for it to close, the elevator feels and seems like it willl fall with people in it and cause an accident"

J House Greenwich

8/10 Good

"Great stay loved the room and the tv in the bathroom mirror was amazing. We ate at Tony’s restaurant while there which was fantastic. My only complaint and area of improvement was the breakfast provided in the AM was awful. Just a few baked pastries,granola bars and yogurt provided. Basically something to grab and go but not sure can really be counted as “breakfast included” other than that though we loved the room and property."

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