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
  • 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 vacation rentals

10.0 out of 10, Exceptional, (30 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is CA $300
CA $529 total
includes taxes & fees
Mar 2 - Mar 3
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Aparthotel in Queens

Starlight Hotel
2.5 star property
8.2 out of 10, Very good, (809 reviews)
"Good service , nice place clean "
United States
victor
The price is CA $148
CA $175 total
includes taxes & fees
Mar 8 - Mar 9
Starlight Hotel
2.0 star property
The price is CA $162
CA $389 total
includes taxes & fees
Mar 2 - Mar 3
Luxury 3BR Home Game Room Free Parking
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is CA $215
CA $454 total
includes taxes & fees
Mar 3 - Mar 4
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
3.0 star property
The price is CA $201
CA $514 total
includes taxes & fees
Mar 2 - Mar 3
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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 CA $150
CA $211 total
includes taxes & fees
Mar 2 - Mar 3
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is CA $211
CA $414 total
includes taxes & fees
Mar 10 - Mar 11
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Vacation Home in Hempstead

Cozy Cottage
The price is CA $143
CA $356 total
includes taxes & fees
Mar 2 - Mar 3
Cozy Cottage

Apartment in White Plains

Elegant Hideaway with Free Parking
2.0 star property
The price is CA $271
CA $514 total
includes taxes & fees
Mar 2 - Mar 3
Elegant Hideaway with Free Parking
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is CA $266
CA $521 total
includes taxes & fees
Mar 2 - Mar 3
Luxe Provincial Style Studio w/ Patio & Parking

Vacation Home in Historic District

Family Cottage with 4 King Beds and Fire Pit
10.0 out of 10, Exceptional, (10 reviews)
"Stayed with our adult children for a family wedding. Everyone enjoyed the spotless, attractive & appointed home with lovely king beds in all the rooms. It was a treat!Host was very attentive, would highly recommend!"
United States
Nancy B.
The price is CA $281
CA $730 total
includes taxes & fees
Mar 2 - Mar 3
Family Cottage with 4 King Beds and Fire Pit

Apartment in Cove - East Side - Shippan

Seabreeze at the beach west beach Stamford ct.
9.8 out of 10, Exceptional, (10 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is CA $196
CA $518 total
includes taxes & fees
Mar 4 - Mar 5
Seabreeze at the beach west beach Stamford ct.
9.8 out of 10, Exceptional, (16 reviews)
"Excellent property close to Fordham, very clean and nice amenities! Hope to stay here on our next visit to see our daughter at Fordham."
United States
Amy B.
The price is CA $266
CA $607 total
includes taxes & fees
Mar 2 - Mar 3
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Beautiful layout. Property had everything that was needed for an awesome stay."
United States
Ashley
The price is CA $476
CA $736 total
includes taxes & fees
Mar 2 - Mar 3
Luxury 3BR Family Home Game Room Parking
The price is CA $190
CA $553 total
includes taxes & fees
Mar 2 - Mar 3
Family-Friendly Retreat With Trampoline & Grill
9.8 out of 10, Exceptional, (10 reviews)
"Clean, modern, convenient property. Online pictures were accurate, check in was easy. Highly recommend. Would stay there again without hesitation."
United States
Rebecca
The price is CA $270
CA $505 total
includes taxes & fees
Mar 2 - Mar 3
Gorgeous, 2- bedroom apartment walking distance to GWB!

Apartment in Piermont

Piermont Oasis
9.8 out of 10, Exceptional, (14 reviews)
"Absolutely perfect location--so lovely to walk to restaurants, ice cream, views, etc. Would definitely stay here again."
United States
joelle a.
The price is CA $164
CA $284 total
includes taxes & fees
Mar 8 - Mar 9
Piermont Oasis
9.2 out of 10, Wonderful, (9 reviews)
"Nice location, clean and comfortable, and looking forward to possibly revisiting."
United States
Doug S.
The price is CA $130
CA $221 total
includes taxes & fees
Mar 15 - Mar 16
Cozy 1-bedroom apartment in Hicksville with WiFi, AC
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is CA $490
CA $751 total
includes taxes & fees
Mar 2 - Mar 3
Luxury 1BR located in Prime Yonkers Area
The price is CA $532
CA $959 total
includes taxes & fees
Mar 2 - Mar 3
Comfortable 1 family home in Tuckahoe that's near train
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.

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Port Chester Hotel Reviews

Find out more about Port Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Port Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Port Chester?

Yes, you can find vacation rentals close to well known sights in Port Chester, or you can choose a secluded option if you're looking for relaxation. 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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: Visitors like this Port Chester vacation home rental. It is equipped with a garden, air-conditioning, and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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?

Cultural attractions to visit include Capitol Theatre and Clay Art Center Gallery. In the larger area, you’ll find Rye Playland and Bruce Museum of Arts and Science.

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.