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

Port Chester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Port Chester vacation rentals

A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

1. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
$364 nightly
The price is $416
Aug 31 - Sep 1
Total with taxes and fees
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
A living room with a sofa, coffee table, bookshelf, and a mirror.

2. Welcoming 1 bedroom apartment in beautiful harbor village.

Welcoming 1 bedroom apartment in beautiful harbor village.
Northport
10.0 out of 10, Exceptional, (1 review)
"Beautiful clean upstairs apartment with a private entrance. Very quiet neighborhood with a small park across the street. Karen, the homeowner who lives downstairs is a wonderful person. The place was perfect for what I needed amd the location was great."
United States
Sallyann S.
$273 nightly
The price is $312
Sep 7 - Sep 8
Total with taxes and fees
Welcoming 1 bedroom apartment in beautiful harbor village.
A wooden deck with a railing overlooking a calm body of water, boats in the distance, and a clear sky.

3. Waterfront Beach Cottage Studio Sunsets Private 90 mins MetLife

Waterfront Beach Cottage Studio Sunsets Private 90 mins MetLife
Northport
9.0 out of 10, Wonderful, (11 reviews)
"Very kind folks here, would stay again"
United States
Ronald T.
$712 nightly
The price is $813
Sep 6 - Sep 7
Total with taxes and fees
Waterfront Beach Cottage Studio Sunsets Private 90 mins MetLife
A house with a white exterior, a brown roof, and a balcony. It is located on stilts over water, surrounded by dense green trees.

4. Waterfront Studio Beach Cottage Wow Sunsets Walk to Village Shops Winery Brewery

Waterfront Studio Beach Cottage Wow Sunsets Walk to Village Shops Winery Brewery
Northport
9.4 out of 10, Exceptional, (18 reviews)
"Great host and property!"
United States
Anonymous traveler
$1,210 nightly
The price is $1,383
Sep 17 - Sep 18
Total with taxes and fees
Waterfront Studio Beach Cottage Wow Sunsets Walk to Village Shops Winery Brewery
A wooden deck with chairs and a kayak, leading to a beach with a view of the ocean.

5. Shore to Shore Coastal Retreat at Asharoken

Shore to Shore Coastal Retreat at Asharoken
Northport
$1,032 nightly
The price is $1,165
Aug 31 - Sep 1
Total with taxes and fees
Shore to Shore Coastal Retreat at Asharoken
A modern kitchen with dark cabinetry, a microwave, and a stove. There is a large flat-screen TV mounted on the wall.

6. 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, (9 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
$369 nightly
The price is $422
Aug 31 - Sep 1
Total with taxes and fees
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
A modern bedroom with a large bed, a small dining area, and a kitchenette.

7. Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (5 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
$383 nightly
The price is $438
Aug 31 - Sep 1
Total with taxes and fees
Luxe Provincial Style Studio w/ Patio & Parking
A modern kitchen with a marble island, bar stools, and a built-in oven.

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

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
$400 nightly
The price is $457
Aug 31 - Sep 1
Total with taxes and fees
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

9. Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
Huntington
9.2 out of 10, Wonderful, (12 reviews)
"Great location & thoughtful amenities."
United States
Joshua
$550 nightly
The price is $628
Sep 8 - Sep 9
Total with taxes and fees
Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village
A room with a dark wooden door, white paneled walls, a woven mirror, a wicker basket, a cushioned chair, and a small round table.

10. Nama-stay, sweet pink Saugatuck Shores beach cottage

Nama-stay, sweet pink Saugatuck Shores beach cottage
Westport
9.2 out of 10, Wonderful, (17 reviews)
"Great fenced in yard for our pup"
United States
Deb S.
$617 nightly
The price is $698
Sep 23 - Sep 24
Total with taxes and fees
Nama-stay, sweet pink Saugatuck Shores beach cottage

11. Modern Apartment with Private Entrance

Modern Apartment with Private Entrance
Historic District
$240 nightly
The price is $272
Aug 31 - Sep 1
Total with taxes and fees
Modern Apartment with Private Entrance
A modern living room with a fireplace, a television, and a dining area with chairs and a table.

12. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (15 reviews)
$598 nightly
The price is $677
Sep 1 - Sep 2
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

13. 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, (84 reviews)
"A beautiful home and you cannot beat the views and location!"
United States
Daniel M.
$469 nightly
The price is $536
Sep 7 - Sep 8
Total with taxes and fees
Captain's Cottage - Cold Spring Harbor Water Views
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

14. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
$219 nightly
The price is $252
Aug 31 - Sep 1
Total with taxes and fees
Guesthouse at Norwalk Inn
A corner seating area with two chairs and a table, a patterned rug, and a wooden railing.

15. King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
$319 nightly
The price is $361
Aug 31 - Sep 1
Total with taxes and fees
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
A hotel room with a bed, desk, chair, and a TV.

16. 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, (13 reviews)
"Ample on street parking - a smooth self check in - a comfortable bed and a clean bathroom in a quiet and safe walkable neighborhood. I did not know NYC could be so user friendly!"
United States
Susan O.
$143 nightly
The price is $159
Sep 1 - Sep 2
Total with taxes and fees
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

17. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature
Cranbury
$382 nightly
The price is $432
Sep 7 - Sep 8
Total with taxes and fees
Gilded Age Luxury Surrounded by Nature
A bedroom with a bed, a round mirror, a door, and wall decorations.

18. 2-bedroom apartmet No cleaning Fee

2-bedroom apartmet No cleaning Fee
West Norwalk
$309 nightly
The price is $350
Sep 7 - Sep 8
Total with taxes and fees
2-bedroom apartmet No cleaning Fee

19. 4 BR VILLA, celebration welcome, No Cleaning fee

4 BR VILLA, celebration welcome, No Cleaning fee
West Norwalk
$669 nightly
The price is $757
Sep 7 - Sep 8
Total with taxes and fees
4 BR VILLA, celebration welcome, No Cleaning fee
A modern kitchen with a dining area, bar stools, and a large wooden table.

20. Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.

Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.
Hicksville
9.6 out of 10, Exceptional, (4 reviews)
"My family and I absolutely loved this home! It had everything we needed and plenty of room for everyone! We def recommend this home"
United States
Erin D.
$1,350 nightly
The price is $1,507
Aug 31 - Sep 1
Total with taxes and fees
Newly Stunningly Updated 4-bedroom house in lovely Hicksville with WiFi, AC.
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

Royal Regency Hotel

Royal Regency Hotel

10/10 Excellent
"Same breakfast everyday"
Amy 1-night trip
Posted 7 hours ago
Royal Regency Hotel

Find out more about Port Chester

Everything you need to know about Port Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Port Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Port Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Port Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Port Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Port Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $174 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Port Chester rentals

At Expedia, we put the best Port Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Port Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Port Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Port Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Port Chester?

Yes, you can find vacation rentals in Port Chester close to Port Chester-Rye Brook Public Library, 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 Hawthorne Beach. While here, Capitol Theatre - Garcia’s and Port Chester-Rye Brook Public Library are other places worth a visit.

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.