Shelter Island vacation rentals

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.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.6°F (2.0°C)	Light Rain	Mostly Sunny	Average	Moderately Low
February	35.8°F (2.1°C)	Light Rain	Mostly Cloudy	Average	Moderately Low
March	39.7°F (4.3°C)	Light Rain	Mostly Sunny	Average	Moderately Low
April	47.5°F (8.6°C)	Light Rain	Mostly Sunny	Average	Average
May	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Average	Average
June	64.9°F (18.3°C)	Light Rain	Mostly Sunny	High	Moderately High
July	73.0°F (22.8°C)	Light Rain	Mostly Sunny	High	Moderately High
August	73.4°F (23.0°C)	Light Rain	Mostly Sunny	High	Moderately High
September	68.2°F (20.1°C)	Light Rain	Mostly Sunny	Average	Average
October	59.7°F (15.4°C)	Light Rain	Mostly Sunny	Low	Average
November	49.6°F (9.8°C)	Light Rain	Mostly Sunny	Low	Average
December	42.1°F (5.6°C)	Light Rain	Mostly Cloudy	Low	Average

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.

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.