Shelter Island Heights holiday rentals

We found 388 holiday rentals — enter your dates for availability
Discover a selection of 33 homes and other holiday rentals in Shelter Island Heights that are perfect for your trip. Whether you're travelling with your children or with friends, holiday homes have the amenities that you expect for your stay, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Shelter Island Heights

Showing deals for:4 Dec - 11 Dec

Spacious Main Floor Living room
Exterior
Pool
Exterior
Exceptional
(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

8% off
AU$13,307
for 7 nights, 1 home
AU$1,901 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Grill + outdoor dining / furniture to dine al fresco!
Living area
Interior
Interior
Exceptional
(42 reviews)

Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

Southold

7% off
AU$8,474
for 7 nights, 1 home
AU$1,211 per night
includes taxes & fees
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
Dining
Private kitchen
Room
Private kitchen
Exceptional
(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

8% off
AU$6,460
for 7 nights, 1 home
AU$923 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Dining
Terrace/patio
Interior
Interior
Exceptional
(19 reviews)

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport

8% off
AU$6,582
for 7 nights, 1 home
AU$940 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Room
Property grounds
Dining
Private kitchen
Exceptional
(8 reviews)

Waterfront Property on Shelter Island

Shelter Island

8% off
AU$7,183
for 7 nights, 1 home
AU$1,026 per night
includes taxes & fees
Waterfront Property on Shelter Island
Hall into sitting room
Master bed onto balcony
Kitchen from dining room
Dining room from kitchen
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
AU$13,781
for 7 nights, 1 home
AU$1,969 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Living area
Outdoor dining
Private kitchen
Living area
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
AU$8,075
for 7 nights, 1 home
AU$1,154 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
Our porch is furnished with plants for a Gilded Age feel
Every season brings special flower blooms
Morning breakfast room
Attention to details and fine workmanship was a sign of wealth both then and now
Exceptional
(37 reviews)

Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

Greenport

12% off
AU$10,740
for 7 nights, 1 home
AU$1,534 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Private kitchen
Pool
Room
Living area
Exceptional
(11 reviews)

Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport

East Marion

8% off
AU$8,620
for 7 nights, 1 home
AU$1,231 per night
includes taxes & fees
Newly renovated ranch w/ large Pool in quiet neighborhood 1 mile from Greenport
Backyard
Kitchen
Shed
Exterior
Exceptional
(106 reviews)

Relax in this light-filled home, steps from the beach and a short walk to town!

Greenport

8% off
AU$4,812
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Property grounds
Property grounds
Pool
Exterior
Exceptional
(87 reviews)

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport

8% off
AU$4,735
for 7 nights, 1 apartment
AU$676 per night
includes taxes & fees
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Private kitchen
Exterior detail
Room
Terrace/patio
Exceptional
(8 reviews)

5 minute walk to beaches and beautiful downtown Greenport

Greenport

8% off
AU$3,471
for 7 nights, 1 home
AU$496 per night
includes taxes & fees
5 minute walk to beaches and beautiful downtown Greenport

  • 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, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The lively area of Shelter Island Heights awaits your stay

Come and experience Shelter Island Heights and its opera, entertainment and theatre scene. Renowned for its island views, camping and beaches, this city welcomes all visitors. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around Shelter Island Heights

Do you want to find things to do in the area? Venture out of your cosy holiday rental and experience everything that makes Shelter Island Heights a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Kontokosta Winery (2.2 mi / 3.6 km)
  • Raphael Winery (6.4 mi / 10.3 km)
  • Pindar Vineyards (6.7 mi / 10.8 km)
  • Bedell Cellars (7 mi / 11.2 km)
  • Noyac Golf Club (7 mi / 11.3 km)
  • Peconic Bay Winery (7.9 mi / 12.7 km)

Exploring the natural landscape of Shelter Island Heights

Travellers enjoy Shelter Island Heights for its island views and beaches. Whether you're an adventurous traveller or just want to appreciate the scenery, Shelter Island Heights is a great place to get out in nature. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Sunset Beach (0.9 mi / 1.4 km)
  • Crescent Beach (1.2 mi / 1.9 km)
  • 67 Steps Beach (2.6 mi / 4.2 km)
  • Orient Point County Park (8 mi / 12.8 km)
  • LongHouse Reserve (10.8 mi / 17.3 km)
  • The Hamptons Beaches (11.3 mi / 18.2 km)

Seasonal weather averages in Shelter Island Heights

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 21°C.

Transport to and around Shelter Island Heights

The nearest airport is in East Hampton, NY (HTO), located 10.2 mi (16.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.2 km) away.

Frequently asked questions

What is the best area to stay in Shelter Island Heights when booking a holiday rental?
When considering a holiday rental in Shelter Island Heights, the area is renowned for its charming atmosphere and picturesque surroundings, making it an excellent choice for a relaxing getaway. This neighbourhood is home to a variety of properties that cater to different tastes and budgets, offering a selection of comfortable accommodations that allow visitors to fully immerse themselves in the local experience.One of the standout features of Shelter Island Heights is its close proximity to some lovely attractions. The beautiful Crescent Beach is a favourite among visitors, providing a great spot for sunbathing and swimming. Additionally, the nearby Shelter Island Historical Society offers a glimpse into the area's rich history, showcasing local artefacts and hosting various community events throughout the year.The overall ambience of Shelter Island Heights is tranquil and inviting, with its quaint streets lined with lovely homes and an abundance of greenery.
Where are the best areas for renting a beach house in Shelter Island Heights?
For renting a beach house in Shelter Island Heights, the area around Crescent Beach is particularly appealing. This charming neighbourhood offers a selection of holiday rentals that provide stunning views of the water and easy access to the beach. Many properties here come equipped with amenities such as private decks, outdoor grills, and spacious living areas, making them superb for families or groups looking to enjoy a seaside retreat.Another popular area is the vicinity of the Shelter Island Yacht Club, where you can find elegant homes with well-maintained gardens and proximity to marinas. These rentals often feature modern kitchens, air conditioning, and communal spaces ideal for entertaining. The nearby Sunset Beach provides a lovely spot for evening strolls and breathtaking sunsets, enhancing the overall beach experience.Additionally, the area is rich in natural beauty, with nearby walking trails and parks, allowing guests to explore the local landscape. Many beach houses also offer easy access to water sports activities, such as kayaking and paddleboarding, ensuring a fun-filled stay.
What is the most popular type of holiday rental accomodation in Shelter Island Heights?
In Shelter Island Heights, holiday houses are the most popular type of holiday rental, with around 78 available throughout the area. These homes are typically spacious and well-suited for families or groups, offering multiple bedrooms, fully equipped kitchens, and outdoor spaces such as patios or gardens for relaxation. Many of these properties are located in serene neighbourhoods, providing a peaceful atmosphere close to the beach and local parks. Additionally, there are several condos available, which often feature modern amenities and communal facilities, appealing to those seeking a more compact accommodation option.
Are there any family house rentals in Shelter Island Heights?
In Shelter Island Heights, there are some family-friendly rentals available, making it an excellent choice for those travelling with children. This picturesque area is known for its charming homes, many of which feature spacious living rooms, fully equipped kitchens, and outdoor areas great for family gatherings. Visitors can enjoy amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.Families will appreciate the nearby parks and beaches, where children can play and explore the natural surroundings. The locale also offers access to scenic walking trails and local dining options that cater to various tastes.
Can I rent a holiday home with a pool or hot tub in Shelter Island Heights?
In Shelter Island Heights, there are around 17 holiday homes available for rent that include pools and hot tubs, making it an excellent choice for travellers seeking relaxation and leisure. This picturesque community is known for its charming atmosphere and proximity to beautiful beaches, providing a great backdrop for a getaway.Many of the rentals feature private pools and hot tubs, alongside outdoor spaces ideal for entertaining or simply enjoying the serene surroundings. Expect amenities such as fully equipped kitchens, spacious living areas, and in some cases, outdoor dining areas and gardens.
Are there pet-friendly house rentals in Shelter Island Heights?
In Shelter Island Heights, travellers can find a selection of pet-friendly house rentals, with around 13 options available. This charming area is known for its tranquil atmosphere and beautiful waterfront views, making it an excellent choice for those looking to enjoy a peaceful getaway with their pets.Many of the holiday rentals in this locality offer amenities such as spacious outdoor areas, which are great for pets to roam, as well as well-equipped kitchens that cater to self-catering needs. Some properties may feature additional comforts like private decks, spacious living areas, and proximity to local beaches, enhancing the overall experience for both travellers and their furry companions.The neighbourhood is also close to pet-friendly points of interest, including several parks and nature trails where pets are welcome.
Are there any remote work holiday rentals in Shelter Island Heights?
In Shelter Island Heights, there are plenty of remote work holiday rentals available, with around 75 options to choose from. This charming area offers a peaceful atmosphere, ideal for those looking to balance work and relaxation. Many properties come equipped with amenities suiting remote workers, such as reliable Wi-Fi, desk spaces, and comfortable seating, ensuring a conducive environment for productivity.The neighbourhood is picturesque, featuring lovely waterfront views and access to local parks, making it a delightful place to unwind after a day's work. Nearby points of interest, including the Shelter Island Heights Pavilion and beautiful beaches, provide superb spots for leisure activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Shelter Island Heights?
In Shelter Island Heights, popular rental amenities include well-equipped kitchens, which allow guests to prepare their own meals, as well as decks or patios for enjoying the fresh air and scenic views. Many properties also feature fireplaces, adding a cosy touch for cooler evenings. For those looking for a bit of luxury, private pools are available in several rentals, providing a great spot for relaxation and fun. Additionally, some accommodations come with blenders, suiting guests who enjoy making smoothies or cocktails during their stay.
When is the best time to visit Shelter Island Heights for a holiday rental?
July is the most popular month to visit Shelter Island Heights, coinciding with the peak season that runs from May to July. This vibrant period draws holidaymakers seeking sun-soaked days and a relaxing coastal atmosphere. With temperatures typically ranging from 20 to 30 degrees Celsius, guests can indulge in outdoor activities such as beach lounging, kayaking, and exploring the picturesque trails that weave through the stunning landscapes.During this peak season, the island comes alive with a variety of events and activities, making it an ideal time for those who thrive in a lively environment filled with fellow travellers. However, if you prefer a quieter experience, consider visiting in December. While this month is considered the low season, it offers a unique charm, allowing you to enjoy the serene beauty of Shelter Island Heights without the hustle and bustle of summer crowds.Ultimately, your best time to book a holiday rental will depend on whether you're drawn to the vibrant summer festivities or the peaceful winter retreat.
What are the top attractions in Shelter Island Heights?
In Shelter Island Heights, visitors can enjoy a serene atmosphere complemented by beautiful natural surroundings. One of the main attractions is the picturesque Crescent Beach, which offers a tranquil spot for swimming and sunbathing. The area is also known for its charming Victorian architecture, which can be appreciated while strolling along the tree-lined streets.The Shelter Island Historical Society features exhibits that highlight the island's rich history, while the nearby Mashomack Preserve offers opportunities for hiking and wildlife observation amidst its diverse ecosystems. For those interested in boating, the local marina provides access to sailing and fishing experiences.
Are all fees included in the Shelter Island Heights holiday homes prices shown on Stayz?
Stayz 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.
Are there any Shelter Island Heights holiday homes with parking?
Stayz offers a wide selection of holiday homes in Shelter Island 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 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.
Are there any discounts for Shelter Island Heights holiday homes?
You can find great discounts on holiday homes in Shelter Island Heights on Stayz, 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.
Can I change or cancel my Shelter Island Heights holiday home booking on Stayz?
To find Shelter Island Heights holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Shelter Island Heights?
A long-stay holiday home in Shelter Island 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Shelter Island Heights holiday home?
Book your Shelter Island Heights holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Shelter Island Heights?
Prices for holiday homes in Shelter Island 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Shelter Island Heights to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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