The Heights vacation rentals
We found 26 vacation rentals — enter your dates for availability
Discover a selection of 10 homes and other vacation rentals in The Heights that are perfect for your trip. Vacation homes provide the amenities you need and want for you and your friends, family, or even pets, such as a fireplace and garden. At the end of the day, you'll be able to choose a rental for everyone's needs, including a place that's non-smoking or offers accessibility.
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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

Fantastic house
This is a fanstastic house, beautifully decorated, and fully outfitted with everything you need. The owner is great--he checked in on us several times to make sure we had everything we needed, which we did. I have rented many VRBO homes, and this one is the best.
Emily C.
Stayed Jul 2024

Gingerbread Cottage
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Allison R.
Stayed Sep 2023

Calm, Peaceful, Wonderful
The care and condition of this house makes it clear that it's well loved, and now we love it too! We spent four weeks in this cozy place, and the house was a peaceful oasis throughout. We're already missing the spacious screened porch / outdoor room at the back, and we hope to return again.
The house is meticulously clean and well stocked. The neighborhood is quiet and calm. The grounds are spacious and well landscaped. Judy was lovely as well—thoughtful, considerate, and just the right amount of communication.
We loved it and will certainly be back.
Josh C.
Stayed Aug 2023

Family Getaway
Virginia was a wonderful and incredibly accommodating host! Our family of 7 (plus one infant) fit comfortably in this clean and welcoming home. The pool was always at the perfect temp and everything one could possibly need for a family getaway was right within the home. Highly recommend!
Shanna Z.
Stayed Jul 2021

The perfect Shelter Island house!
We are just back from a glorious August week at this lovely house. We were already excited by the pictures and early conversations with the lovely owner, but the reality was even better!
The house is large and comfortably and so well appointed (e.g., lovely soap, all the cooking stuff you could ever need, tons of games, beach accessories, hammocks, seating aplenty everywhere, fresh flowers, etc.). The location is spot-on -- you can walk to town and also to a number of beaches, but you are on a quiet street with limited traffic and a huge backyard.
We were two families with four very small children between us and the house was the perfect size. Everyone had plenty of space to do their own thing and to be together.
I cannot say enough good things about this spot and about Rob who was such a gracious and easy host during every interaction.
Ellen W.
Stayed Aug 2019

We had a terrific time - the house was perfect for us.
We really enjoyed our stay. Diana was extremely responsive and everything was perfectly set up. The house is truly a “home” and the location is great - very central to everything - beaches, Marie Eiffel, IGA etc. The pool and outdoor shower were key for our family! We will be back for sure :)
Crista T.
Stayed Aug 2019

Quiet Little Getaway and Quite a nice little Getaway!
"Hi Jennifer, I just wanted to let you know how much our family’s time at your home on Shelter Island meant to us. Your care and pride in your family’s respite shines through as soon as you step through the door. Although we always try to leave a home as clean and tidy as when we arrive, we felt so endeared to your hospitality we talked as a family how to keep things nice, avoid cup rings on wooden pieces, watch for any issues, add to your shell collection on the front porch railing, leave a few things for the freezer and pantry! Thank you for having thought of all of the little things which a family might need in the kitchen, we loved cooking and eating together in your well stocked (essentials and spices and gadgets and more!) It was a restful and healing stay for us. We all enjoyed the pool and, especially I, the hot tub, so relaxing and such a treat to be outdoors a little longer this season. Thank you for sharing your quiet little getaway with our family! Best wishes, Jennifer October 2021
Jennifer B.
Stayed Oct 2021

Eastern Beach
The property was lovely, big enough, pool was great. My only complaints were: 1. grill not functioning and 2. odors in some spaces from lack of dehumidification and lack of AC.
Anne F.
Stayed Jul 2024
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental in The Heights?
In The Heights, vacation houses are the most popular type of rental accommodation, with several available throughout the area. These homes typically offer ample space with multiple bedrooms, fully equipped kitchens, and cozy living areas, making them ideal for families or groups. Many properties also feature outdoor spaces like private gardens or patios where guests can relax and enjoy the neighborhood's vibrant setting.
Are there any beach house rentals in The Heights?
In The Heights, there are about 15 beach house rentals available. These properties typically feature spacious living areas, fully equipped kitchens, and outdoor patios or decks that offer views of the surrounding area. Many of the rentals are situated close to local parks and the scenic Hudson River waterfront, making them ideal for travelers who enjoy outdoor activities and exploring the vibrant neighborhood.
How much does it cost to rent a vacation home in The Heights?
Prices for vacation 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 vacation 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.
What are popular rental amenities in The Heights?
In The Heights, travelers can expect a variety of popular rental amenities that enhance their stay. Many vacation rentals feature fully equipped kitchens, allowing guests to prepare their own meals and enjoy dining at home. Outdoor spaces are also common, with decks or patios providing a pleasant environment to relax and take in the neighborhood's charm. For added comfort, many properties include fireplaces, great for cozy evenings. Additionally, porches or lanais are available in some rentals, offering a great spot for morning coffee or evening gatherings. Some properties even come with a blender, ideal for whipping up smoothies or cocktails during a stay.
Can I find family house rentals in The Heights?
In The Heights, New York, there are several family-friendly house rentals available, making it an excellent choice for those traveling with children. This vibrant neighborhood is known for its rich cultural scene and beautiful parks. Many properties feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for kids to enjoy.Visitors can easily access nearby highlights such as Fort Tryon Park, which offers lush gardens and stunning views of the Hudson River, as well as the Cloisters museum, showcasing medieval art and architecture. Additionally, families will appreciate the convenience of local amenities such as grocery stores, restaurants, and cafes that cater to diverse tastes.
Can I rent a vacation home with a pool or hot tub in The Heights?
In The Heights, New York, there are several vacation homes available for rent that feature pools and hot tubs. This vibrant neighborhood, known for its stunning views of the Hudson River and rich cultural diversity, offers a variety of rental options. Many properties come equipped with amenities such as private pools, hot tubs, outdoor seating areas, and fully equipped kitchens, making them ideal for relaxation and entertainment.
Are there any The Heights vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in The Heights with parking available—perfect for families or travelers 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 book pet-friendly vacation rentals in The Heights?
In The Heights, New York, travelers can find several pet-friendly vacation rentals that cater to both comfort and convenience. Many of these properties come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy fresh air. The neighborhood itself offers a vibrant setting with local parks, including Fort Tryon Park, which features beautiful gardens and scenic walking paths, great for pet owners looking to spend time outdoors with their furry companions. Additionally, the area boasts pet-friendly cafes and shops, ideal for those traveling with pets.
Can I find long-stay vacation rentals in The Heights?
A long-stay vacation rental in The Heights is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit The Heights for a vacation rental?
The best time to visit The Heights for a vacation rental is during the peak season from May to July. This vibrant period draws travelers eager to experience the area's dynamic atmosphere and lush surroundings. With warmer temperatures ranging from the mid-70s to low 90s Fahrenheit, outdoor activities flourish, making it an ideal time for sightseeing, enjoying local parks, and exploring the unique cultural offerings of the neighborhood.July stands out as the most popular month, bringing a lively energy as visitors flock to enjoy outdoor festivals, street fairs, and a variety of dining options that spill out onto the sidewalks. The warm weather is superb for leisurely strolls along the picturesque streets, where you can discover local art and architecture.For those looking for a more budget-friendly option, consider planning your visit in December. This month, while quieter, offers the charm of holiday decorations and a cozy atmosphere superb for enjoying the local culinary scene and cultural events without the high tourist traffic.Ultimately, your ideal time to visit The Heights should align with your preferences for lively activities and socializings or a more relaxed exploration of the area.
Are there any remote work vacation rentals in The Heights?
In The Heights, New York, there are several vacation rentals that cater to remote work needs. Many of these properties are equipped with high-speed Wi-Fi, ensuring a reliable internet connection for work-related tasks. Additionally, travelers can expect amenities like in-room safes for secure storage and comfortable workspaces, making it easy to balance work and leisure during their stay. The vibrant neighborhood offers a mix of cultural experiences, with nearby parks and dining options that provide a refreshing break from work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a The Heights vacation rental?
Book your The Heights vacation 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 vacation 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 showcase the neighborhood's rich history and vibrant culture. One of the most great sites is the historic Fort Tryon Park, which offers stunning views of the Hudson River and is home to the Cloisters, a branch of the Metropolitan Museum of Art dedicated to medieval art and architecture. The park features beautiful gardens and walking paths, great for leisurely strolls.The neighborhood is also known for its diverse culinary scene, with numerous restaurants and cafes offering a taste of Dominican cuisine and other international flavors. Visitors can enjoy local favorites along Broadway, where lively storefronts and cultural influences create a dynamic atmosphere.Additionally, the area is rich in history, with landmarks like the Morris-Jumel Mansion, which is the oldest house in Manhattan and offers guided tours that delve into the history of the Revolutionary War.
Can I change or cancel my The Heights home rental booking on Vrbo?
To find The Heights vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.
Vrbo also offers support via live chat through our Help Center, 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 organizing 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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