Shelter Island vacation rentals

We found 2,328 vacation rentals — enter your dates for availability

Discover a selection of 88 homes and other vacation rentals in Shelter Island that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll have the amenities you expect and more, which might include WiFi and a fireplace. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Shelter Island

Showing deals for:Mar 27 - Apr 3

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Pool
10 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
Price is $1,164
$8,150 for 7 nights
All fees included
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

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Find out more about Shelter Island

Why visit Shelter Island

  • Scenic beaches: Enjoy the beautiful shorelines and tranquil waters perfect for relaxation and recreation.
  • Rich historical charm: Explore historical buildings and landmarks that reflect the island's unique heritage.
  • Outdoor activities: Engage in hiking, biking, and nature walks in picturesque parks and natural settings.
  • Romantic getaways: Experience cozy accommodations and intimate settings ideal for couples.
  • Family-friendly excursions: Discover activities and attractions suitable for visitors of all ages.

Popular types of accommodation in Shelter Island

Discover the charm of Shelter Island with our selection of vacation rentals. Whether you’re looking for houses, cozy cottages, or stylish apartments, we have the perfect options for your getaway. Explore our listings for shelter island rentals and find the ideal house rentals in Shelter Island, NY. Whatever your travel plans, you’ll enjoy transparency, savings, and reassurance while making unforgettable memories in this beautiful destination.

  • Houses: The top choice for visitors, offering spacious and comfortable accommodations ideal for families or groups.
  • Cottages: A charming option for those seeking a cozy, quaint atmosphere, perfect for a relaxing getaway.
  • Apartments: Convenient and often centrally located, apartments provide a home-like feel for solo travelers or couples.
  • Condos: These modern, well-appointed spaces offer excellent amenities and are great for enjoying a resort-like experience.
  • Villas: Luxurious and spacious, villas provide a lavish escape with stunning views and private outdoor spaces.**

Top attractions in and around Shelter Island

Shelter Island is perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore beautiful beaches, historical buildings, and urban parks. The attractions cater to those looking for cultural experiences, family fun, and relaxation by the shore, making it an ideal destination for a memorable vacation in New York.

  • 67 Steps Beach: A charming beach located 4 miles from Shelter Island, 67 Steps Beach offers a relaxed atmosphere with beautiful views and tranquil waves, perfect for sunbathing and unwinding.
  • Gardiner's Bay Country Club: Nestled within Shelter Island, this picturesque golf course provides a challenging yet enjoyable experience amidst lush landscapes, making it ideal for golf enthusiasts.
  • Orient Point County Park: Situated 8 miles away, this urban park features family-friendly activities, scenic walking trails, and ample outdoor space, making it perfect for picnics and nature exploration.

Things to do recommended for couples

For a romantic getaway on Shelter Island, visit Kontokosta Winery for enchanting views and fine wines, then enjoy a fun round at Shelter Island Whale's Tail mini-golf. Don't miss Raphael Winery, where you can savor exquisite vintages in a charming setting. Perfect for couples seeking memorable experiences.

Things to do recommended for families

Families can enjoy a ride on the Greenport Carousel just 3 miles away, unwind at Cedar Point County Park 5 miles from Shelter Island, or relax at Goldsmith's Inlet Park, located 7 miles away, offering beautiful outdoor spaces for wellness and fun.

Things to do recommended for groups

Explore the Greenport Farmers' Market for local goods, enjoy a captivating show at Bay Street Theatre, or tee off at Noyac Golf Club for a fun day outdoors. Each of these experiences offers a unique taste of Shelter Island's charm, perfect for group travelers.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Shelter Island

If you're traveling with a group, family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to guide you.

  • Traveling to Shelter Island with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Shelter Island with young kids: Traveling with little ones can be a bit of a challenge. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Shelter Island: For many families, a vacation wouldn’t be the same without their furry companion. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Shelter Island: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Shelter Island

Exploring Shelter Island, New York, offers a delightful blend of scenic beauty and historical charm. This idyllic island getaway is perfect for outdoor enthusiasts and romantic vacations alike. Nearby areas like Shelter Island Heights provide picturesque views and family-friendly excursions. With opportunities to unwind in private estates and enjoy budget-friendly activities, your stay promises relaxation and memorable experiences amidst stunning surroundings.

  • Hamptons: Located 9 miles from Shelter Island, the Hamptons are a popular getaway known for their stunning beaches and charming outdoor experiences. This area attracts visitors seeking romance and relaxation, offering a range of activities from golfing to attending lively music concerts. The scenic beaches, including family-friendly stretches, provide a perfect backdrop for sunbathing or beach sports. Don’t miss the chance to explore the quaint shops and fine dining options that characterize this upscale coastal region.
  • Greenport: Just 3 miles from Shelter Island, Greenport is a picturesque village that embodies the charm of a seaside community. Visitors flock here for its outdoor adventures and romantic atmosphere, with ample opportunities for beach outings and waterside dining. The town features a vibrant arts scene, with music concerts and events that draw locals and tourists alike. Explore the beautiful beaches and family-friendly areas, or attend conferences and events at the local venues that highlight Greenport's unique cultural offerings.
  • Sag Harbor: Situated 5 miles from Shelter Island, Sag Harbor is a historic whaling port that has transformed into a trendy destination for outdoor enthusiasts. This charming city boasts beautiful beaches and inviting parks, perfect for a romantic day out. Enjoy various activities including golfing and skiing in nearby fields. The local beaches are ideal for sun-soaked afternoons, while the parks provide serene spots for picnics. With its rich maritime history and vibrant community, Sag Harbor is a must-visit on your vacation.

Best time to go to Shelter Island

If you're planning a trip to Shelter Island, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyHighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyLowAverage
November49.6°F (9.8°C)Light RainMostly SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowAverage

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to refine your search by price, location, and rental type.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your reservation. Being the planner has its perks. When you join our travel rewards program, OneKey, you’ll gain immediate access to exclusive member savings and the opportunity to earn and redeem OneKeyCash on qualifying bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient platform for you to create new trips, manage your plans, and keep track of your bookings. Your saved or booked properties are organized into categories: Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Beautiful Shelter Island will entice you

The area's history and museums are just a few of the reasons to vacation in Shelter Island. Travelers to this scenic city praise the island views, kayaking and parks. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Shelter Island - a plantation nation

Aside from just feeling the sand between your toes, Shelter Island has a wealth of history. You can easily spend an hour or so exploring the historic Sylvester Manor, an educational farm and manor house which dates back to 1652. A former plantation, the manor house and grounds are open to the public for tours between Tuesday and Saturday. Now you've got a taste for island history, dig deep into Shelter Island's past at the Havens House Museum. Run by the Shelter Island Historical Society, Havens House was built in 1743 and features a fascinating array of period displays.

An island of peachy beach adventures

Shelter Island life is all about the beach, just ask any local. There are 3 main beaches on the island. Crescent Beach attracts watersports enthusiasts, who come for a cheery paddle around the island. It has a cafe, lifeguards, and several places to rent kayaks and paddleboards. The pristine sands of Shell Beach and Wades Beaches are perfect for sunbathing and beach picnics. It's also popular with the golfing crowd, who come to tee off on the island's 2 golf courses that, along with a minigolf course, will satisfy any wannabe Tiger Woods.

Summer swelters on Shelter Island

Shelter Island has been popular weekend getaway for savvy New Yorkers for decades. Although a year-round vacation destination, that's not to say the weather is great all year round. During the summer months, expect dry days with plenty of sunshine and a higher than average humidity. However, in winter, the mercury drops dramatically and snow is all but guaranteed. If you book a Shelter Island vacation rental in the shoulder seasons, spring and fall, you'll find cool but sunny days, and lots more rain, so be prepared to get soaked.

Discover the Sound of silence at the Mashomack Preserve

Less than a 10-minute ferry ride from the eastern shores of Long Island, Shelter Island lies a 100 miles east of New York City. Surrounded by the cool clear waters of the Block Island Sound, Shelter Island hosts loads of marine life, with dolphins, and humpback and pilot whales regularly spotted from the shore. Large swathes of the island are part of the Mashomack Preserve, which has 10 miles of coastline and salt marshes. It's a big draw for the state's birdwatchers, who flock to spot osprey, great blue heron, and the snowy egret.

How to get to and around Shelter Island

The nearest airport is in MacArthur Airport (ISP), located 44.1 mi (70.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to East Hampton, NY (HTO), which is 8.8 mi (14.2 km) away.

Frequently asked questions

What is the best area to stay in Shelter Island when booking a vacation rental?
When booking a vacation rental in Shelter Island, New York, one of the best areas to consider is the Crescent Beach neighborhood. This charming area offers stunning waterfront views and easy access to pristine beaches, making it ideal for relaxation and outdoor activities. Crescent Beach is known for its friendly space and is superb for families or couples looking to unwind by the shore. Nearby, you can explore the beautiful Sunset Beach, which is famous for its breathtaking sunsets and vibrant beach club scene, providing a superb spot for dining and socializing.

Another fantastic option is the Silver Beach area, which boasts a tranquil setting with a mix of vacation homes and charming cottages. This neighborhood is a great choice for those looking to enjoy a peaceful retreat while still being close to various attractions. In Silver Beach, you can take advantage of the local parks, such as the serene Silver Beach Park, where you can enjoy picnicking and nature walks. The area also offers convenient access to the Shelter Island Historical Society, providing a glimpse into the island's rich history and culture.

Overall, both Crescent Beach and Silver Beach have a range of vacation rentals available, ensuring that you'll find something that suits your needs.
How much does it cost to rent a vacation home in Shelter Island?
Prices for vacation rentals in Shelter Island 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 Shelter Island 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 Shelter Island vacation house rentals?
You can find great discounts on house rentals in Shelter Island 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.
Where are the best areas for renting a beach house in Shelter Island?
For renting a beach house in Shelter Island, New York, consider the areas around Crescent Beach and Shell Beach, both of which offer picturesque waterfront views and access to sandy shores. Properties in these neighborhoods often feature amenities such as private beach access, outdoor decks for sunbathing, and spacious living areas great for family gatherings. Many rentals come equipped with modern kitchens, allowing guests to prepare meals while enjoying the coastal ambiance.

The area near the Shelter Island Yacht Club is also appealing, with options that provide marina views and easy access to boating activities. Here, you can find charming homes with outdoor grills, picnic areas, and sometimes even private docks for watercraft. This neighborhood is ideal for travelers who appreciate a nautical atmosphere and want to partake in sailing or fishing.

Additionally, the surrounding nature trails and parks, like Mashomack Preserve, enhance the appeal of the area. Rentals nearby often feature amenities such as kayaks or bicycles for exploring the scenic landscapes. Find your rental near the beach in Shelter Island.
What is the most popular type of vacation rental accomodation in Shelter Island?
In Shelter Island, vacation houses are the most popular type of rental, with about 69 available throughout the area. These properties often feature spacious layouts, multiple bedrooms, and amenities such as private decks or patios for enjoying the serene surroundings. Many vacation houses are situated near points of interest like the picturesque beaches and the local nature preserves, providing guests with easy access to outdoor activities.

In addition to vacation houses, several cottages and apartments can also be found, offering a more intimate setting. Cottages typically have cozy interiors and may include amenities like kitchenettes and outdoor grilling areas, while apartments usually feature fully equipped kitchens and comfortable living spaces.
Are there any family house rentals in Shelter Island?
In Shelter Island, there are numerous family-friendly house rentals available, with around 45 options to choose from. This picturesque destination is great for families looking to enjoy a mix of relaxation and outdoor activities. Many homes come equipped with spacious living rooms, fully stocked kitchens, and outdoor decks or patios ideal for family gatherings. Some properties even feature private pools, game rooms, or access to nearby beaches, enhancing the overall experience for visitors.

The island is known for its natural beauty, with scenic spots like the Mashomack Preserve offering trails for hiking and wildlife observation, making it a great place for family outings. Additionally, the charming local area features quaint shops and restaurants that cater to all tastes. See all family-friendly rentals in Shelter Island.
Can I rent a vacation home with a pool or hot tub in Shelter Island?
In Shelter Island, travelers can find a variety of vacation homes available for rent that feature pools and hot tubs, with around 25 options to choose from. This picturesque destination offers a tranquil atmosphere with beautiful waterfront views and lush landscapes, making it ideal for a relaxing getaway.

Many of these rentals come equipped with private pools, hot tubs, and spacious outdoor areas for lounging and entertaining. Expect amenities such as fully equipped kitchens, outdoor dining spaces, and comfortable living areas, superb for families or groups. Some properties may also offer additional features like fire pits, barbecue grills, and access to nearby beaches, enhancing the overall vacation experience. Find your rental in Shelter Island with a pool or a hot tub.
Can I find long-stay vacation rentals in Shelter Island?
A long-stay vacation rental in Shelter Island 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.
Are there pet-friendly house rentals in Shelter Island?
In Shelter Island, there are numerous pet-friendly house rentals available, providing a great option for travelers looking to enjoy a getaway with their furry companions. Many of these rentals are situated in serene, wooded areas, allowing for a peaceful retreat. Expect amenities such as spacious backyards, outdoor patios for relaxing, and comfortable living spaces equipped with modern kitchens and multiple bedrooms, making them suitable for families or groups.

Shelter Island is known for its scenic beauty, and visitors can enjoy nearby spots like Mashomack Preserve, which offers miles of hiking trails great for walking dogs and exploring nature. Additionally, the area features several pet-friendly beaches where you can enjoy the waterfront with your pet. See all pet-friendly rentals in Shelter Island.
Are there any remote work vacation rentals in Shelter Island?
In Shelter Island, there are numerous remote work vacation rentals available, with around 63 options to choose from. This picturesque island offers a tranquil setting ideal for combining work and leisure, surrounded by the natural beauty of the East End of Long Island. Many properties are equipped with essential amenities for remote work, including reliable Wi-Fi, dedicated office spaces, desks, and comfortable desk chairs, ensuring a productive work environment. Additionally, some rentals may provide features like laptop workspaces and computer monitors, superb for those needing a more comprehensive setup.

Travelers can also enjoy the island's charming neighborhoods and points of interest, such as the serene beaches and local parks. The nearby Shelter Island Heights area is particularly appealing, with its friendly space and access to nature trails. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Shelter Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Shelter Island 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.
What are popular rental amenities in Shelter Island?
In Shelter Island, travelers can expect a range of popular amenities in vacation rentals, enhancing their stay in this serene getaway. Most rentals come equipped with WiFi, allowing guests to stay connected while enjoying the island's natural beauty. Kitchens are a standard feature, providing the convenience of home-cooked meals, and many rooms include appliances like blenders and coffee/tea makers for added comfort. Outdoor spaces, such as decks or patios, are also common, offering superb spots for relaxation and enjoying the fresh air.
When is the best time to visit Shelter Island for a vacation rental?
The best time to visit Shelter Island for a vacation rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts travelers seeking a quintessential summer experience, where outdoor activities abound and the island's charm comes to life. With average temperatures ranging from the mid-60s to mid-80s Fahrenheit, visitors can comfortably enjoy the beautiful beaches, scenic trails, and local events.

During these months, you can partake in a variety of activities such as kayaking, sailing, and exploring the picturesque landscapes. The lively atmosphere is complemented by numerous art shows, farmers' markets, and outdoor concerts, making it an ideal time for families and friends to gather.

For those looking for a more budget-friendly option, consider visiting in November. This month offers a unique opportunity to experience Shelter Island's serene beauty without the hustle and bustle of peak tourist season. The crisp air and tranquil surroundings provide a superb backdrop for peaceful walks and stunning autumn views.

Ultimately, your choice of when to visit Shelter Island will depend on whether you prefer the energetic summer vibe or the calm, reflective nature of late fall.
How early should I book a Shelter Island vacation rental?
Book your Shelter Island 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 Shelter Island?
In Shelter Island, visitors can engage in a tranquil atmosphere filled with natural beauty and charming attractions. One of the top spots is the Mashomack Preserve, a stunning nature reserve offering miles of hiking trails, birdwatching, and scenic views of the surrounding waters. For a taste of local history, the Shelter Island Historical Society and its museum provide insights into the island's unique heritage.

Additionally, the picturesque beaches, such as Crescent Beach and Wades Beach, are superb for sunbathing and swimming, with family-friendly environments. The island's vibrant community can be experienced at the local shops and restaurants in the Heights area, where you can find delightful dining options and artisanal boutiques. Exploring the waterfront areas also offers opportunities for boating, kayaking, and enjoying beautiful sunsets.
Can I change or cancel my Shelter Island home rental booking on Vrbo?
To find Shelter Island 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 Shelter Island 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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