Westchester County holiday lettings

We found 1,311 holiday rentals — enter your dates for availability

Discover a selection of 215 homes, 169 apartments and other holiday rentals in Westchester County that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the amenities that you need and want, such as Wi-Fi and cable TV. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Popular cities in Westchester County

Holiday rentals with weekly discounts - Westchester County

Showing deals for:26 Sept - 3 Oct

Why visit Westchester County

  • Outdoor Adventures: Enjoy a variety of outdoor activities in beautiful parks and nature reserves, perfect for enthusiasts of all ages.
  • Charming Towns: Explore delightful towns like Port Chester, known for their vibrant atmosphere and friendly locals.
  • Cultural Scene: Experience a rich cultural landscape with museums, theatres, and local festivals.
  • Historical Sites: Discover fascinating historical landmarks that showcase the region's heritage.
  • Diverse Accommodation: Choose from an array of holiday rentals, from charming homes to modern apartments, catering to every traveller's needs.

Popular types of accommodation in Westchester County

Westchester County offers an array of holiday rentals to suit every traveller's needs. From charming houses to modern apartments and stylish condos, you're sure to find the perfect base for your adventures. Whether you're seeking spacious bedroom apartments or convenient apartment rentals, Westchester County has something for everyone, making it an ideal destination for those looking to explore the beauty of New York State.

  • Houses: The top choice for those seeking a holiday rental in Westchester County, offering ample space and privacy for families or groups.
  • Apartments: A popular second option, ideal for couples or solo travellers looking for comfort and convenience in the heart of the county.
  • Condos: The third most sought-after accommodation type, providing a blend of luxury and homely amenities for a relaxing stay.
  • Cottages: A charming fourth choice, perfect for those wanting a quaint retreat in a picturesque setting.**

Top attractions in Westchester County

Westchester County is an ideal destination for outdoor enthusiasts, families, and those seeking a vibrant city atmosphere. Visitors can explore a variety of attractions, including urban parks, modern colleges and universities, and nature reserves. With a rich cultural scene and ample opportunities for outdoor activities, Westchester County offers a delightful experience for all types of travellers looking to enjoy a memorable holiday.

  • Westchester County Center: A vibrant arts centre, the Westchester County Center hosts a variety of cultural events, including concerts and exhibitions, providing a fantastic atmosphere to experience local art and performances.
  • Sarah Lawrence College: This modern university boasts a picturesque campus with a creative and intellectual vibe, perfect for leisurely strolls and appreciating the unique architecture and gardens.
  • Rye Playland: An iconic amusement park, Rye Playland offers thrilling rides and family-friendly attractions amidst a charming seaside setting, ensuring a delightful day of outdoor adventure.

Things to do recommended for couples

For a charming couple's experience in Westchester County, visit the Tarrytown Music Hall for an enchanting concert. The venue exudes a lively atmosphere, perfect for enjoying an evening together filled with music and entertainment. It's a delightful way to create lasting memories.

Things to do recommended for families

Families will have a fantastic time at Legoland Discovery Center Westchester's AdventureZone, enjoy the serene atmosphere of Harbor Island Park, and engage in fun activities at Armonk Indoor Sports Center's sports facilities. Each location offers a unique blend of adventure, relaxation, and sports for all ages.

Things to do recommended for groups

In Westchester County, groups can enjoy shopping at The Westchester Mall, catch a show at the Capitol Theatre, and explore Westchester's Ridge Hill for a vibrant mix of entertainment and dining options, all while soaking up the local atmosphere.

Booking with Vrbo is a breeze

Looking to make the most of your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo accommodation that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Where to stay in Westchester County

Westchester County offers a delightful blend of outdoor adventures and family-friendly attractions. Explore charming towns like Port Chester, renowned for its vibrant atmosphere and friendly locals. Enjoy historical sites, beautiful parks, and scenic views that cater to all ages. Nearby counties enhance your experience with diverse neighbourhoods, making Westchester an ideal base for a memorable getaway in New York.

  • Yonkers: Nestled along the Hudson River, Yonkers boasts a vibrant urban atmosphere that appeals to families, business travellers, and city explorers alike. The city features extensive shopping areas and modern squares that cater to all your retail desires. Yonkers is home to various attractions, including the beautiful waterfront parks and the historic Philipse Manor Hall, which offers a glimpse into the city’s past. The lively tourist precinct ensures there is always something happening, making it an ideal base for your Westchester County adventure.
  • White Plains: As the hub of Westchester County, White Plains combines urban sophistication with a welcoming community vibe. Perfect for families and visitors on business, the city is renowned for its shopping areas and bustling arts scene, featuring theatres and cultural centres. The modern squares serve as social gathering spots, where you can enjoy outdoor dining or vibrant community events. Don’t miss the opportunity to explore the local landmarks, which reflect the city’s rich history while providing a contemporary backdrop for your holiday.
  • New Rochelle: Situated along the Long Island Sound, New Rochelle is a charming city that offers a delightful blend of family-friendly activities and urban excitement. The city features an array of shopping centres and theatres, ensuring entertainment for all ages. Explore the picturesque waterfront or take a leisurely stroll through the town's squares, which are lined with cafes and boutiques. With its relaxed atmosphere and numerous attractions, New Rochelle is a wonderful destination for those looking to experience the best of Westchester County.

What do I need to keep in mind when booking a vacation in 'Westchester County

If you're planning a trip with friends, family, pets, or seeking extended stays, it's essential to prioritise your preferences when filtering options. Here are some helpful booking tips for using Vrbo.

  • Traveling to Westchester County with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Westchester County with young kids: Travelling with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Westchester County: For many, a family holiday wouldn’t be the same without their beloved pet 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 all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Westchester County: If you're in search of holiday rentals with offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up right where you left off, and manage your travel arrangements. You can easily access properties you’ve saved or booked, which are now conveniently organised under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The historical area of Westchester County awaits your stay

Enjoy the area's history, art galleries and entertainment with a rental holiday home in Westchester County. Well known for its wildlife, sporting events and hiking, this welcoming city won't disappoint. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Westchester County

Are you searching for attractions to visit while you're in town? Venture out of your holiday home and experience everything that Westchester County has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Bronx Zoo (19.3 mi / 31.1 km)
  • Legoland Discovery Center Westchester (11.3 mi / 18.2 km)
  • Rye Playland (12.5 mi / 20.1 km)
  • Chelsea Piers (15.4 mi / 24.7 km)
  • Putnam County Golf Course (18.4 mi / 29.7 km)
  • Ridgewood Country Club (19.3 mi / 31 km)

Exploring the natural features in Westchester County

Whether you're looking for fun outdoor activities or just want to take in the scenery, Westchester County is a great spot to appreciate mother nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Central Park (25.2 mi / 40.6 km)
  • Bryant Park (27.3 mi / 43.9 km)
  • Rockefeller State Park Preserve (2.3 mi / 3.7 km)
  • Nyack Beach State Park (6.1 mi / 9.8 km)
  • Croton Point Park (6.6 mi / 10.7 km)
  • Rockland Lake State Park (6.8 mi / 10.9 km)

Travelling to and around Westchester County

Fly into White Plains, NY (HPN-Westchester County), the closest airport, located 6 mi (9.6 km) from the city centre.

If you're travelling by train, Ossining Station, White Plains Metro-North Railroad Station and Croton-Harmon Station are the main stations that serve the city. You might consider catching a ride on the metro at Mount Vernon West Station for ease of access to the rest of the city.

Frequently asked questions

What is the best area to stay in Westchester County when booking a holiday rental?
Among the more popular areas to book your holiday home in Westchester County is Yonkers. Spend your getaway here and have fun visiting its leading attractions, including Empire City Casino and Yonkers Raceway.
What is the most popular type of holiday rental accommodation in Westchester County?
The most in-demand types of holiday rentals in Westchester County are houses. Searching for something different? Vrbo has many options to match our guests' requirements, so you'll see holiday homes in all sizes, and for all budgets. The ideal home away from home is waiting for you --- find yours today.
How much does it cost to rent a holiday rental in Westchester County?
The average price for a holiday rental in Westchester County depends on a number of factors, including season, length of stay and property type. Whether you'd like a sprawling house with room for friends and family or a cosy condo ideal for just you and the kids, just enter your travel dates to view stays with fantastic value.
How much does it cost to rent a beach house in Westchester County?
When you travel and the style and size of the property will influence the cost of your beachside holiday rental. Click on your Westchester County travel dates to view your options on Vrbo. Can't live without a hot tub? Use the filters to choose the features and amenities you want in your rental.
What are popular rental amenities in Westchester County?
Some of the most popular rental amenities people search for in Westchester County are off-street parking options, a fridge and a microwave oven. Whether you're hitting the road with family, pals or even pets, Vrbo holiday homes provide the best amenities for chilling out with the people you love.
Are there large group holiday rentals in Westchester County?
Westchester County has 34 holiday homes that can fit 10 or more guests. These stays come with plenty of space to enjoy good times with family and friends.
What are the top attractions for families in Westchester County?
Keeping the kids amused during your holiday in Westchester County is a cinch with these leading family-friendly attractions:
  • Empire City Casino
  • Capitol Theatre
  • The Westchester Mall

Can I find two-bedroom holiday rentals in Westchester County?
Take your pick of 32 two-bedroom holiday rentals in Westchester County. Settle the kids into the second room or maybe fill it with a couple of your favourite people. There's enough space for whoever's fortunate enough to be joining your adventure.
Are there holiday rentals with WiFi in Westchester County?
Choose from 78 holiday rentals with WiFi in Westchester County. If you want to disconnect from daily life during your escape, but still want to be connected to the internet, these getaways are just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How old do you have to be to rent a holiday rental in Westchester County?
Age restrictions can differ between properties on Vrbo, so be sure to check the rules of the holiday home in Westchester County you're interested in. But normally, it's 16, 18 or 21.
How long can I rent a holiday rental in Westchester County for?
The length of time you can rent a holiday rental in Westchester County is up to the property. Just enter your desired dates to display a list of options offering extended stays. With many features like air conditioning and laundries, as well as some offering weekly or monthly discounts, you're sure to discover somewhere just right to call your home away from home in Westchester County.

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