Westchester holiday lettings

We found 83 holiday rentals — enter your dates for availability

Discover a selection of 16 homes and other holiday rentals in Westchester that are perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as a fireplace and garden. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to rent a holiday home in Westchester?
Prices for holiday rentals in Westchester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Westchester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Westchester holiday house rentals?
You can find great discounts on house rentals in Westchester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Westchester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Westchester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay holiday rentals in Westchester?
A long-stay holiday rental in Westchester is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Westchester for a holiday rental?
The best time to visit Westchester is during the peak season from January to March, with March being particularly popular among travellers seeking a warm escape. This period is ideal for those looking to enjoy outdoor activities, as the region experiences pleasant temperatures averaging between 18 to 25 degrees Celsius. Visitors can take advantage of the lovely weather for sightseeing, exploring local parks, or indulging in outdoor dining.

March offers a vibrant setting as many events and festivals take place, allowing guests to immerse themselves in the local culture while enjoying the beautiful surroundings. The area is bustling with activity, but there are also plenty of options for those who prefer a more relaxed pace.

If you're looking for a more budget-friendly option, consider planning your visit in October. This month provides a quieter experience, making it an excellent time for leisurely strolls and enjoying the local scenery without the crowds. Plus, the pleasant weather continues, ensuring comfort for outdoor pursuits.

Ultimately, your choice of when to visit Westchester should reflect your preferences for lively events and warm weather or a more tranquil retreat with beautiful autumn scenes.
How early should I book a Westchester holiday rental?
Book your Westchester holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Westchester, Florida, United States of America?
In Westchester, Florida, visitors can explore several attractions that showcase the local culture and outdoor beauty. The area is known for its family-friendly parks, with Westchester Park offering playgrounds, sports fields, and picnic areas, making it an excellent spot for relaxation and recreation. Nearby, the Miami-Dade College West is an educational hub that often hosts cultural events and community activities.

For shopping and dining, the Westchester shopping centre features a variety of stores and restaurants, providing a convenient place for visitors to enjoy local cuisine and retail therapy.
Can I change or cancel my Westchester home rental booking on Vrbo?
To find Westchester holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Westchester holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

More holiday ideas