The Heights holiday lettings
We found 26 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in The Heights that are perfect for your trip. Holiday homes provide the amenities that you need and want for you and your friends, family or even pets, such as parking and a hot tub. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.
Find spaces that suit your style
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Find the best place to stay - The Heights

Newly renovated! Shelter Island Gem, 3 blocks from Sunset Beach
Sleeps 6 · 3 bedrooms · 2 bathrooms

Away From it All! Bright, generous and well located 5-bedroom/3.5 Heights house
Sleeps 10 · 5 bedrooms · 3+ bathrooms

Spacious house next to the beach, Ferry and Eateries.
Sleeps 11 · 6 bedrooms · 4+ bathrooms

NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
Sleeps 6 · 3 bedrooms · 2 bathrooms

Shelter Island Waterview Villa
Sleeps 6 · 1 bedroom · 1 bathroom
Top rated rentals - The Heights

Perfect location
This property was superb
Shelter Island stunning
sarah D.
Stayed Aug 2019
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
How much does it cost to rent a holiday home in The Heights?
Prices for holiday rentals in The Heights 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 The Heights 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 The Heights holiday house rentals?
You can find great discounts on house rentals in The Heights 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 The Heights holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in The Heights 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 The Heights?
A long-stay holiday rental in The Heights 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 The Heights for a holiday rental?
The best time to visit The Heights for a holiday rental is during the peak season from May to July, with July being the most popular month. This vibrant period attracts a variety of tourists eager to experience the bustling atmosphere, lovely parks, and cultural attractions that The Heights has to offer. With warm temperatures ranging from 20 to 30 degrees Celsius, it's an ideal time for outdoor activities, enjoying the local cuisine, and exploring the charming neighbourhood.In July, visitors can engage in the lively community spirit, as numerous events and festivals take place, showcasing local art, music, and food. Take advantage of the pleasant weather by strolling through the area's parks or visiting nearby landmarks that are easily accessible.For those looking to save on their travel expenses, consider planning your trip in December. Though it's the low season, this month offers a great experience with festive decorations and a quieter atmosphere great for a cosy getaway. You can enjoy the charm of The Heights at a more relaxed pace, making it an excellent option for those seeking a peaceful retreat.
How early should I book a The Heights holiday rental?
Book your The Heights 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 The Heights, New York, United States of America?
In The Heights, New York, visitors can explore a variety of attractions that highlight the area's rich cultural heritage and stunning views. One of the most great sites is Fort Tryon Park, where you can enjoy picturesque gardens and scenic walking paths, as well as the renowned Cloisters museum, which showcases medieval European art and architecture. The park provides breathtaking views of the Hudson River and the Palisades, making it a great spot for a leisurely stroll.Another highlight is the vibrant George Washington Bridge, which offers impressive views and is an iconic landmark of New York City. The area is also known for its diverse dining options, featuring a mix of Dominican, Puerto Rican, and other Caribbean cuisines, particularly along Broadway and in the surrounding streets.Additionally, the neighbourhood boasts a rich history, with sites such as the Dyckman Farmhouse Museum, which provides insight into 18th-century life in the area.
Can I change or cancel my The Heights home rental booking on Vrbo?
To find The Heights 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 The Heights 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.
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