Port Chester Vacation Rentals

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Our top choices for Port Chester vacation rentals

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
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 $302
CA $572 total
includes taxes & fees
Apr 20 - Apr 21
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Charming 1-bedroom basement apartment in Floral Park with WiFi and AC

Charming 1-bedroom basement apartment in Floral Park with WiFi and AC
Floral Park
8.0 out of 10, Very good, (7 reviews)
"Communication was great; all my questions were answered, which I appreciated. The place was clean and easy to get to by bus. "
United States
Vivian
The price is CA $167
CA $232 total
includes taxes & fees
Apr 17 - Apr 18
Charming 1-bedroom basement apartment in Floral Park with WiFi and AC

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

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (31 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is CA $198
CA $398 total
includes taxes & fees
Apr 21 - Apr 22
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
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 $185
CA $412 total
includes taxes & fees
Apr 19 - Apr 20
Luxury 1BR located in Prime Yonkers Area

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is CA $244
CA $490 total
includes taxes & fees
Apr 28 - Apr 29
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Cozy Cottage

Cozy Cottage
Hempstead
The price is CA $144
CA $357 total
includes taxes & fees
Apr 23 - Apr 24
Cozy Cottage

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (75 reviews)
"Location was perfect!"
United States
Linda J P.
The price is CA $283
CA $650 total
includes taxes & fees
Apr 20 - Apr 21
Captain's Cottage - Cold Spring Harbor Water Views

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

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is CA $130
CA $185 total
includes taxes & fees
Apr 19 - Apr 20
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is CA $198
CA $431 total
includes taxes & fees
Apr 19 - Apr 20
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (16 reviews)
"Excellent space and accommodations. "
United States
angela c.
The price is CA $165
CA $286 total
includes taxes & fees
Apr 28 - Apr 29
Piermont Oasis

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
8.8 out of 10, Excellent, (10 reviews)
"Had a great stay "
United States
Desiree
The price is CA $130
CA $222 total
includes taxes & fees
Apr 19 - Apr 20
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is CA $199
CA $311 total
includes taxes & fees
May 12 - May 13
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

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 CA $208
CA $279 total
includes taxes & fees
Apr 18 - Apr 19
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
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 $268
CA $524 total
includes taxes & fees
Apr 20 - Apr 21
Luxe Provincial Style Studio w/ Patio & Parking

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is CA $254
CA $510 total
includes taxes & fees
Apr 17 - Apr 18
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is CA $412
CA $676 total
includes taxes & fees
May 1 - May 2
Luxury NYC Home Game Room Free Parking

Family-Friendly Retreat w/ Trampoline & Grill

Family-Friendly Retreat w/ Trampoline & Grill
Locust Valley
The price is CA $206
CA $576 total
includes taxes & fees
Apr 17 - Apr 18
Family-Friendly Retreat w/ Trampoline & Grill

Modern 1BR / Free Parking / Comfortable Stay

Modern 1BR / Free Parking / Comfortable Stay
Bryn Mawr
The price is CA $111
CA $427 total
includes taxes & fees
Apr 30 - May 1
Modern 1BR / Free Parking / Comfortable Stay

Modern 1BR Apt / Free Parking / Near NYC

Modern 1BR Apt / Free Parking / Near NYC
White Plains
10.0 out of 10, Exceptional, (1 review)
"Very clean, fully stocked with all you need to cook full meals. If coming back to the area, 10/10 would stay again."
United States
Mike J.
The price is CA $124
CA $427 total
includes taxes & fees
Apr 19 - Apr 20
Modern 1BR Apt / Free Parking / Near NYC

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is CA $118
CA $421 total
includes taxes & fees
Apr 18 - Apr 19
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
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.
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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 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 Greenwich Point Park. In the larger area, you’ll find Clay Art Center Gallery and Rye Playland.

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.