Shelter Island holiday lettings

Why visit Shelter Island

• Stunning beaches: Enjoy idyllic shores perfect for relaxation and romantic getaways, such as Silver Beach.
• Outdoor activities: Explore nature with various outdoor pursuits, ideal for adventure seekers and tranquillity lovers alike.
• Charming firepits: Experience cosy evenings under the stars around delightful firepits.
• Historic charm: Discover Shelter Island's rich history through its beautiful architecture and local culture.
• Variety of accommodations: Choose from charming cottages, private homes, and comfortable apartments for a memorable stay.

Popular types of accommodation in Shelter Island

You're off to Shelter Island, and the next step is selecting the perfect place to stay. Explore our top offerings for Shelter Island holiday rentals, including charming houses, quaint cottages, and comfortable apartments. Whether you're looking for a spacious house rental or a delightful holiday home, you'll find a variety of options to suit your needs and ensure a memorable getaway.

• Houses: The top choice for holiday rentals in Shelter Island, ideal for groups or families seeking a home-away-from-home experience.
• Cottages: A charming and cosy option, perfect for those wanting a quaint retreat amid the scenic beauty of Shelter Island.
• Apartments: A convenient and flexible choice, offering a home-like atmosphere with easy access to local amenities.
• Condos: A modern accommodation type that combines comfort and style, often located in vibrant areas.
• Villas: Luxurious and spacious, these properties provide an upscale experience for a memorable getaway.**

Top attractions in and around Shelter Island

Shelter Island is perfect for outdoor and romantic getaways, with its stunning beaches, historic buildings, and urban parks. Visitors can immerse themselves in local culture while enjoying various activities, such as relaxing by the beach or exploring nature. Don't miss the charming firepit, ideal for cosy evenings under the stars. Whether you're seeking adventure or tranquillity, Shelter Island has something for every traveller.

• 67 Steps Beach: A picturesque beach characterised by its sandy shores and scenic views. The 67 steps leading down to the beach provide a unique descent, offering a lovely spot for relaxation and sunbathing.
• Sag Harbor Marine Park: This vibrant marina offers a blend of adventure and outdoor fun. Enjoy water sports, fishing, or simply soaking up the beach atmosphere while taking in stunning views of the harbour.
• Gardiner's Bay Country Club: Nestled within Shelter Island, this charming golf course features beautifully manicured greens and a tranquil setting, perfect for both seasoned golfers and novices alike.

Things to do recommended for couples

For a romantic getaway on Shelter Island, indulge in wine tasting at Kontokosta Winery or Pindar Vineyards, both offering enchanting atmospheres. For a bit of fun, try your hand at mini golf at the Shelter Island Whale's Tail, perfect for some light-hearted competition and adventure together.

Things to do recommended for families

Families visiting Shelter Island can enjoy a delightful ride on the Greenport Carousel, just 1.9km away, and unwind at Cedar Point County Park and Goldsmith's Inlet Park, both offering fantastic relaxation vibes within a short distance, perfect for a memorable day out.

Things to do recommended for groups

Experience a captivating performance at Bay Street Theatre, just 3.1km from Shelter Island, or explore local produce at the Greenport Farmers' Market, located 1.9km away. For some outdoor fun, enjoy a round of golf at Noyac Golf Club, 3.7km from the island.

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

If you're travelling with a group, family, pets, or seeking longer stays, be sure to filter according to your key preferences. Here are some helpful Vrbo booking tips to assist 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 space for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
• Traveling to Shelter Island with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is wise.
• Taking your pets with you to Shelter Island: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo accommodations that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
• Planning for a long term stay visiting Shelter Island: If you’re in search of holiday rentals offering discounts 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 accommodations. It might also be worth considering features such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Shelter Island

During your visit to Shelter Island, immerse yourself in its stunning scenery and delightful beaches, perfect for a romantic getaway or a family holiday. Explore nearby Fishers Island for a charming day excursion, or unwind at Silver Beach. Whether you're seeking budget-friendly options or simply want to relax, Shelter Island and its surroundings offer a captivating blend of historical charm and family-friendly activities, ensuring a memorable summer escape.

• Hamptons: The Hamptons, located 5.6km from Shelter Island, is a renowned holiday destination famous for its stunning beaches and luxurious atmosphere. Visitors flock to this area for a romantic getaway or outdoor adventures, where you can bask in the sun on pristine sands or enjoy water sports. Golf enthusiasts will appreciate the numerous golf courses, while music lovers can attend lively concerts. With family-friendly beaches and picturesque lakes, the Hamptons seamlessly blend relaxation with excitement, making it a must-visit locale.
• Greenport: Situated a mere 1.9km from Shelter Island, Greenport is a charming village that offers an enchanting seaside experience. Known for its outdoor activities and romantic setting, this destination is perfect for couples and families alike. Enjoy a leisurely stroll along the waterfront, explore local shops, or indulge in fresh seafood at one of the quaint restaurants. Greenport also hosts music concerts and events throughout the year, ensuring a vibrant atmosphere. With its inviting beaches and event conference venues, Greenport is a delightful place to explore.
• Sag Harbor: Just 3.1km from Shelter Island, Sag Harbor is a picturesque town steeped in maritime history. Visitors come to enjoy its beautiful beaches and outdoor spaces, perfect for a romantic outing or family fun. Experience the thrill of skiing or relax in nearby parks while taking in the stunning coastal views. The area is dotted with golf courses for avid players, and the family-friendly beaches provide a perfect spot for relaxation. Sag Harbor’s blend of history, beachside charm, and recreational activities makes it an ideal destination for all.

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

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. You may also enjoy considerable savings by booking a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a handy platform for you to plan new adventures, resume your previous arrangements, or manage your travel itinerary. You can easily access properties you've saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.