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Port Chester holiday lettings

We found 400 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Port Chester to find one that's perfect for your trip. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as a fireplace and garden. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Port Chester

Showing deals for:7 Nov - 14 Nov
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Why visit Port Chester

  • Charming urban parks: Enjoy the serene atmosphere of Port Chester's well-maintained parks, perfect for family outings and relaxation.
  • Rich cultural experiences: Immerse yourself in local art, music, and heritage that reflect the vibrant community spirit.
  • Delightful shopping: Stroll through picturesque streets lined with unique shops and boutiques, offering a variety of local goods.
  • Culinary delights: Savor diverse local cuisine at numerous eateries, showcasing the area's rich culinary landscape.
  • Proximity to beautiful beaches: Explore nearby beaches for a refreshing escape, ideal for sunbathing and leisure activities.

Popular types of accommodation in Port Chester

Discover the charm of Port Chester with our selection of holiday rentals tailored to suit your needs. Whether you're seeking a cosy apartment, a spacious private vacation home, or a modern condo, we have options to fit every preference. Explore our range of rental properties in Port Chester and find the perfect base for your adventures. Enjoy transparency, savings, and peace of mind while planning your getaway with us.

  • Apartments: The most sought-after option for holiday rentals in Port Chester, offering a range of amenities for a comfortable stay.
  • Houses: A popular choice for larger groups or families, providing a home-away-from-home experience.
  • Condos: Well-liked for their convenient locations and modern facilities, ideal for short or extended stays.
  • Cottages: Charming and often set in picturesque locations, perfect for a relaxing getaway.
  • Villas: Luxurious accommodations that offer spacious living and upscale amenities for an indulgent retreat.**

Top attractions near Port Chester

Port Chester is an ideal destination for families and culture enthusiasts, offering a delightful mix of entertainment and outdoor experiences. Visitors can explore urban parks, modern universities, and nearby beaches, making it a perfect spot for those seeking a blend of relaxation and cultural immersion. With a variety of attractions available, Port Chester promises memorable experiences for all travellers.

  • Rye Playland: This charming amusement park features a unique blend of vintage rides and modern attractions, all set against a picturesque waterfront. Ideal for families, it offers outdoor fun with thrilling roller coasters and serene kiddie rides, ensuring a memorable day out.
  • Westchester County Center: A cultural hub, this arts centre hosts a variety of events including concerts, exhibitions, and trade shows. Its vibrant atmosphere makes it a great place to immerse yourself in the local art scene and enjoy live performances.
  • Greenwich Avenue: A bustling street known for its chic shops and eateries, Greenwich Avenue offers a delightful urban experience. Stroll along the avenue, indulge in retail therapy, and savour diverse culinary delights in this lively city setting.

Things to do recommended for couples

For a romantic getaway in Port Chester, enjoy a concert at Tarrytown Music Hall, unwind with a couple’s treatment at Hand & Stone Massage and Facial Spa, or indulge in luxury at Greenwich Polo Club. Each offers a unique atmosphere perfect for couples.

Things to do recommended for families

While in Port Chester, families can have a thrilling time at Chelsea Piers, just 5.6km away, offering various sports activities. For relaxation, Harbor Island Park, 3.1km away, is perfect for unwinding. Additionally, the Legoland Discovery Center, 6.2km away, guarantees an adventurous day for all ages.

Things to do recommended for groups

Groups visiting Port Chester can enjoy a show at the historic Capitol Theatre, indulge in shopping at The Westchester Mall, or unwind with a round of golf at the nearby Westchester Country Club, all while soaking in the local culture and atmosphere.

What do I need to keep in mind when booking a vacation in 'Port Chester

If you're travelling with a group, family, pets, or planning for an extended stay, it's important to select the right priorities when filtering your options. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Port Chester with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Port Chester with young kids: Journeying with young children can present its own set of challenges. It's important to prioritise their comfort and safety, alongside suitable facilities like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Port Chester: For many, a family holiday wouldn't be the same without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Port Chester: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Port Chester

Port Chester offers a delightful blend of family-friendly attractions and cultural experiences, perfect for a memorable holiday. Explore the charming streets lined with delightful shops, savour local cuisine, and take in the picturesque views. Just a short distance away, you'll find beautiful beaches and welcoming neighbourhoods that exude warmth and friendliness. Whether you're seeking relaxation or entertainment, Port Chester and its surrounding areas present an array of options to enhance your vacation.

  • Rye Brook: Situated a mere 1.2km from Port Chester, Rye Brook is an ideal destination for families seeking a blend of culture and entertainment. Visitors can explore local theatres and enjoy a day at the amusement park, making it a perfect spot for family outings. The area is also home to historic buildings and a modern college, providing a touch of educational charm. Whether you're enjoying a performance or the thrills of a theme park, Rye Brook promises a well-rounded travel experience.
  • Rye: Also located 1.2km away from Port Chester, Rye is known for its outdoor activities and family-friendly atmosphere. The city offers a delightful mix of entertainment options, including theatres and shopping areas. Families can spend time at the beach or visit the local theme park, making it a great place to unwind and enjoy quality time together. With its historic buildings and scenic spots, Rye invites visitors to explore and appreciate its picturesque charm.
  • Greenwich: Just 1.9km from Port Chester, Greenwich is a vibrant city that caters to families, outdoor enthusiasts, and urban explorers alike. The city boasts excellent shopping areas and cultural venues, including theatres that host a variety of performances. Visitors can enjoy the stunning beaches and tranquil lakes, providing a perfect backdrop for relaxation and leisure. The tourist precinct ensures there's always something happening, making Greenwich a lively addition to your travel itinerary.

Best time to go to Port Chester

If you're planning a trip to Port Chester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January31.8°F (-0.1°C)Light RainMostly SunnyAverageSlightly Low
February33.3°F (0.7°C)Light RainMostly SunnyAverageSlightly Low
March39.7°F (4.3°C)Light RainMostly SunnySlightly HighSlightly Low
April50.2°F (10.1°C)Light RainMostly SunnySlightly HighAverage
May60.1°F (15.6°C)Light RainMostly SunnyAverageAverage
June69.1°F (20.6°C)Light RainMostly SunnyAverageAverage
July76.1°F (24.5°C)Light RainMostly SunnySlightly HighSlightly High
August74.8°F (23.8°C)Light RainMostly SunnyAverageSlightly High
September68.4°F (20.2°C)Light RainMostly SunnyAverageAverage
October57.9°F (14.4°C)Light RainMostly SunnySlightly LowAverage
November46.6°F (8.1°C)Light RainMostly SunnySlightly LowAverage
December38.1°F (3.4°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your upcoming holiday? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you might find considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides you with a convenient area to plan new adventures, manage your travel arrangements, and keep track of your reservations. Your saved or booked properties are neatly organised into categories: Potential, Upcoming, or Current Trips. To discover the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Travel to lively Port Chester

Take a holiday to Port Chester and enjoy the area's live music, theatre scene and art galleries. Renowned for its local tours, baseball games and opera houses, this city welcomes all visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Port Chester

Are you searching for top things to see and do while you're in town? Venture out of your cosy holiday rental and experience everything that makes Port Chester a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bronx Zoo (15.2 mi / 24.5 km)
  • Rye Playland (2.5 mi / 4 km)
  • Bayville Adventure Park (7.8 mi / 12.6 km)
  • Chelsea Piers (8.6 mi / 13.9 km)
  • Legoland Discovery Center Westchester (10.3 mi / 16.6 km)
  • Harbor Links Golf Course (12.2 mi / 19.7 km)

Exploring the natural landscape of Port Chester

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Port Chester. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Hawthorne Beach (1.1 mi / 1.7 km)
  • Greenwich Point Park (4.3 mi / 7 km)
  • West Beach (7.9 mi / 12.7 km)
  • Cove Island Park (9.2 mi / 14.7 km)
  • Sands Point Preserve (10 mi / 16.1 km)
  • Glen Island Park (10.2 mi / 16.5 km)

How to get to and around Port Chester

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 5 mi (8.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to LaGuardia Airport (LGA), which is 19.1 mi (30.7 km) away.

Frequently asked questions

How much does it cost to rent a holiday rental in Port Chester?
The average price for a holiday rental in Port Chester depends on several factors, including property type, length of stay and season. Whether you're looking for a sprawling house with room for friends and family or a cosy cottage for just you and your sweetheart, just enter your dates of travel to find stays with exceptional value.
How much does it cost to rent a beach house in Port Chester?
Prices for beach houses in Port Chester will vary depending on the style and size of the property and time of year you're travelling. All you have to do is enter your travel dates into Vrbo and the number of guests to see your options and prices. From there you can use our filter tool to refine your search results by ratings, amenities and more.
What are the top attractions for families in Port Chester?
Keeping the kids occupied during your stay in Port Chester is easy with these fabulous family-friendly attractions:

  • West Beach
  • Hawthorne Beach
  • Cummings Park Beach

How old do you have to be to rent a holiday rental in Port Chester?
The minimum required age is typically 16, 18 or 21. It can change from one property to another on Vrbo, so look at the rules of your preferred Port Chester holiday rental before you book.
How long can I rent a holiday rental in Port Chester for?
It all depends on the Port Chester property. To view all available options offering extended stays, just enter your travel dates and number of guests into Vrbo. Look forward to having the whole property to yourself, along with amenities such as a fully-equipped kitchen and a backyard where your little ones can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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