Shelter Island vacation rentals

We found 2,336 vacation rentals — enter your dates for availability

Discover a selection of 90 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:May 22 - May 29

Image gallery for AMAGANSETT 2 ACRE, 3000 Sq Ft 4 BDR MODERN W/ 20 x 40 POOL, NEAR BEACH & TOWN

Pool
9.8 out of 10, Exceptional, (73 reviews)
Exceptional
(73 reviews)

AMAGANSETT 2 ACRE, 3000 Sq Ft 4 BDR MODERN W/ 20 x 40 POOL, NEAR BEACH & TOWN

Amagansett

13% off
Price is $1,690
$11,829 for 7 nights
All fees included
AMAGANSETT 2 ACRE, 3000 Sq Ft 4 BDR MODERN W/ 20 x 40 POOL, NEAR BEACH & TOWN

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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, New York, United States of America when booking a vacation rental?
When considering a vacation rental in Shelter Island, New York, the Shelter Island Heights neighborhood stands out as a prime choice. This area offers a charming, relaxed atmosphere with stunning views of the surrounding water. It's known for its picturesque streets and historic homes, making it a lovely spot for leisurely strolls. One of the top attractions here is the Shelter Island Heights Historic District, where visitors can appreciate beautiful architecture and the local heritage.

Another great option is Silver Beach, which is superb for those who enjoy outdoor activities. The beach itself is a serene place to unwind, and nearby, you can find the popular Shell Beach, which offers excellent opportunities for swimming and sunbathing. The proximity to these beautiful natural spaces enhances the appeal of staying in this area.

While the total number of vacation rental properties can fluctuate, Shelter Island Heights and Silver Beach have a diverse range of options, from quaint cottages to larger homes, ensuring that you can find something that fits 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, travelers should focus on the picturesque areas near Crescent Beach and Shell Beach. These locations offer a serene coastal atmosphere with beautiful sandy shores and stunning views of the surrounding waters. Many rental properties in these areas come equipped with essential amenities such as private decks, outdoor grills, and spacious living areas, making them great for family gatherings or relaxing getaways.

Additionally, the area surrounding the Shelter Island Yacht Club provides access to lovely waterfront properties that often feature docks for boating enthusiasts, as well as easy access to local beaches. Many of these homes include features like modern kitchens, beach gear, and outdoor seating areas, enhancing the beachside experience.

For those looking to explore beyond the beach, the nearby Mashomack Preserve offers hiking trails and opportunities for wildlife viewing, adding an outdoor adventure component to the stay. Rentals here may also include amenities such as bicycles or kayaks for guests to enjoy the natural beauty of 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 around 69 available throughout the area. These houses typically feature spacious living areas, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking comfort and convenience. Many also boast outdoor spaces such as decks or gardens, great for enjoying the serene surroundings. Additionally, there are several cottages and apartments available, offering cozier options for travelers looking for a more intimate stay.
Are there any family house rentals in Shelter Island?
In Shelter Island, there are numerous family-friendly house rentals available, with around 44 options for travelers to choose from. This charming locale is great for families seeking a peaceful retreat, with properties scattered throughout the island. Many homes offer spacious living areas, fully equipped kitchens, and outdoor patios where families can enjoy meals together or relax after a day of exploring.

Visitors will appreciate amenities such as private pools, game rooms, and access to bicycles for exploring the scenic surroundings. Proximity to nearby attractions like the beautiful beaches of Crescent Beach and Shell Beach, as well as the serene nature trails in Mashomack Preserve, make these rentals an excellent choice for both relaxation and adventure.
Can I rent a vacation home with a pool or hot tub in Shelter Island?
In Shelter Island, there are several vacation homes available for rent that feature pools and hot tubs, with around 27 options to choose from. This picturesque destination offers a blend of tranquility and natural beauty, making it an ideal spot for relaxation. Travelers can find vacation rentals in various neighborhoods, including the serene areas near Crescent Beach and Silver Beach, where many properties boast private pools, hot tubs, and spacious outdoor areas for lounging.

Amenities commonly found in these rentals include fully equipped kitchens, spacious living rooms, and outdoor dining spaces, superb for enjoying meals al fresco. Some properties may also feature landscaped gardens, outdoor grills, and easy access to nearby beaches, enhancing the overall vacation experience.
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, travelers will find a variety of pet-friendly house rentals available, with approximately 32 options to choose from. Many of these properties offer a blend of comfort and convenience, featuring amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like decks or patios, great for enjoying the serene surroundings.

The island itself is known for its beautiful parks and natural areas, making it a great destination for pet owners. Places like Mashomack Preserve offer extensive trails where pets are welcome, allowing for scenic walks and exploration of the local flora and fauna. Additionally, the nearby Crescent Beach provides a lovely spot for a stroll along the shoreline, where leashed pets can enjoy the fresh air and ocean views.
Are there any remote work vacation rentals in Shelter Island?
In Shelter Island, there are numerous remote work vacation rentals available, with around 68 options that cater specifically to those looking to combine work and leisure. Many of these properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspace desks, and printing facilities, making it easy for travelers to stay productive during their stay.

Travelers can expect a range of accommodations, from cozy cottages to spacious homes, often featuring comfortable living areas and fully equipped kitchens. Some properties also offer outdoor spaces, allowing for a refreshing break while enjoying the beautiful surroundings of Shelter Island. The island is known for its tranquil atmosphere, making it an ideal spot for remote work, with local attractions such as beaches, parks, and charming shops providing opportunities for relaxation after a busy workday. 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, popular rental amenities include well-equipped kitchens, allowing guests to prepare their own meals with ease. Many rentals feature decks or patios where visitors can relax and enjoy the tranquil surroundings, enhancing their outdoor experience. Fireplaces are often available, providing a cozy atmosphere during cooler evenings. Additionally, amenities like blenders are commonly found for those looking to whip up smoothies or cocktails. Onsite parking is also a standard offering, making it convenient for guests traveling with their own vehicles.
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, New York, United States of America?
In Shelter Island, visitors can enjoy a tranquil escape with a variety of attractions spread across the island. The beautiful beaches, such as Crescent Beach and Shell Beach, offer picturesque views and opportunities for swimming and sunbathing. The Mashomack Preserve, a stunning nature reserve, features miles of hiking trails and diverse wildlife, making it superb for nature lovers and outdoor enthusiasts.

The charming village of Dering Harbor provides a quaint atmosphere with lovely waterfront views, while the Shelter Island Historical Society offers insight into the island's rich history through its exhibits. Additionally, the island is known for its scenic spots like Sunset Beach, which is ideal for watching breathtaking sunsets. Travelers can also explore local shops and restaurants in the Heights area, where fresh seafood and local cuisine are highlights.
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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