Discover Your Perfect Port Chester Vacation Homes

Best Vacation Homes in Port Chester

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Port Chester Luxury Rentals

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Port Chester Pet Friendly Vacation Rentals

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8.4 (64 Reviews)
Hotel
Delamar Greenwich Harbor
  • Air Conditioner
  • Parking
  • Pet Friendly
View Availability
See More Pet-Friendly Vacation Rentals in Port Chester on PetFriendly.io

Why Choose Rent By Owner for your Port Chester Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Best Times to Visit Port Chester

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, as this destination offers different attractions and activities depending on the season, making it essential to plan your vacation when the weather and local events align with your preferences.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, this area experiences warm weather ideal for outdoor activities and exploring local attractions.

Average Temperature Daytime: around 80°F to 85°F - Nighttime: 60°F to 65°F
autumn
Fall (September to November)

Autumn brings vibrant foliage and pleasant temperatures, making it a popular time to visit here and enjoy outdoor leisure.

Average Temperature Daytime: approximately 70°F to 75°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Winter (December to February)

The winter months tend to be quieter with cooler temperatures, offering a peaceful escape from the crowds.

Average Temperature Daytime: around 35°F to 45°F - Nighttime: 20°F to 30°F
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Spring (March to May)

Early spring sees fewer visitors as the region transitions into warmer weather, providing a serene setting for those seeking tranquility.

Average Temperature Daytime: roughly 50°F to 60°F - Nighttime: 35°F to 40°F

Weekly Weather Forecast for Port Chester

How to Book Your Port Chester Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in Port Chester

More Top-Rated Vacation Rentals in Port Chester Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy outdoor dining areas perfect for relaxing meals amid scenic surroundings.
  • Make the most of private gardens or landscaped yards to unwind in nature.
  • Take advantage of spacious patios or decks ideal for entertaining guests or enjoying a sunrise.
  • Benefit from access to shared or private pools, offering refreshing escapes during warm days.
  • Explore nearby walking trails or pathways that showcase the natural beauty of the region.
  • Utilize outdoor fire pits or grills for cozy evenings and barbecues with family and friends.
  • Relax in outdoor lounge areas designed for soaking up the sunshine and enjoying outdoor leisure time.

Top Attractions Around Port Chester

What attractions are nearby?

In this vibrant region, you can enjoy a variety of outdoor activities, cultural experiences, and dining options just minutes from your vacation rental, making it easy to explore everything that this destination has to offer.

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Family Activities

  • Port Chester Waterfront Park: Enjoy a family picnic and outdoor activities along the scenic waterfront in this charming part of town.
  • Playland Park: Experience classic amusement rides and games that promise fun-filled days just a short drive away in nearby Rye Beach.
  • Rye Nature Center: Discover the region’s natural beauty through guided walks and educational programs suitable for children and adults alike.
  • Historic Greenwich Point Park: Explore walking trails and beaches at this peaceful destination offering stunning views and family-friendly recreation near here.
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Adult Activities

  • Wine Tasting Tours: Discover local wineries and enjoy guided tastings that showcase the region's vibrant viticulture scene.
  • Golfing Experiences: Play a round at nearby golf courses renowned for their scenic fairways and challenging greens, perfect for a relaxing day outdoors.
  • Dining Out in the Area: Savor diverse culinary options at highly-rated restaurants offering everything from contemporary cuisine to classic American fare.
  • Art and Cultural Events: Attend galleries, live performances, and cultural festivals that highlight the area's creative spirit and local talent.

Other Places to Stay in Port Chester, NY

Rye Brook
Rye Brook Vacation Rentals
Capitol Theatre
Capitol Theatre Vacation Rentals
Clay Art Center Gallery
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Port Chester Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take advantage of the area's diverse culinary scene by trying local restaurants and cafes to fully experience the region's flavor.
  • Plan for Nearby Attractions: Incorporate visits to nearby cultural or outdoor spots to enrich your stay in this destination and make the most of your time here.
  • Utilize Public Transportation: Use regional transit options to easily access key areas without the hassle of driving, allowing for a more relaxed vacation experience.
  • Book Strategic Accommodation: Choose accommodations close to the main attractions or transportation hubs to maximize convenience and explore effortlessly during your visit.

Transportation Options

  • Port Chester Railroad Station: Convenient for travelers seeking direct train connections to New York City and other regional destinations, making it easy to explore the area without a car.
  • Local Bus Services: Several bus routes serve the region, providing affordable transportation options for getting around within Port Chester and nearby communities.
  • Taxi and Rideshare Services: Taxis and rideshare apps like Uber and Lyft are readily available here, offering flexible and on-demand transportation throughout the area.
  • Car Rentals: Renting a vehicle locally offers the freedom to explore beyond the immediate vicinity of your vacation rental and venture into surrounding attractions at your own pace.

Local Customs Options

  • Irish Heritage Celebrations: You’ll find that Irish cultural traditions are warmly celebrated here, especially during local St. Patrick’s Day festivities that highlight the area's rich Irish roots.
  • Seafood Dining Etiquette: When dining out in this region, expect a strong emphasis on seafood customs, reflecting the area's proximity to water and its historic maritime heritage.
  • Community Service Events: Participating in community service is a valued custom, with local events often organized to foster neighborhood connections and support local charities.
  • Seasonal Festivals: Seasonal festivals showcasing regional arts and crafts occur regularly, offering you an authentic taste of local culture throughout your stay.

Frequently Asked Questions About Port Chester?

1. What are the top vacation rentals in Port Chester?

There are a lot of options in Port Chester. If you plan on staying in the Port Chester area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Port Chester:

2. Which vacation homes in Port Chester are best for families?

If you are looking for a family-friendly vacation home in Port Chester, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Port Chester:

3. How many Rentbyowner vacation rentals are available in Port Chester?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 79 in the Port Chester area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Port Chester. 

4. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the host directly to understand the terms and any applicable fees.

5. How do I know if my reservation is secure when booking a vacation rental in this region?

Secure booking is guaranteed through the platform's trusted payment systems and verified hosts. Be sure to read reviews and confirm the property's credentials before confirming your reservation.

6. Are there any additional fees I should be aware of when booking a rental here?

Additional fees may include cleaning fees, service charges, or local taxes. These will be detailed in the listing, and you can always reach out to the host for clarification before finalizing your booking.

7. What amenities are typically available in vacation rentals around this destination?

Most properties offer essential amenities such as Wi-Fi, kitchen facilities, and parking. Specific amenities are detailed in each listing, so reviewing the property description will help you find the best fit for your stay.

8. How do I communicate with the host in case I have questions about the rental during my stay?

You can contact the host directly through the messaging system on the booking platform. Clear communication ensures your questions are answered and your stay goes smoothly.