Shelter Island Vacations from ￥390,206

Things to do in and around Shelter Island

Shopping

For a delightful shopping experience in Shelter Island, visit the Greenport Farmers' Market, only 4.8km away, for local goods. The Style Bar, located 8.0km away, offers trendy clothing. If you're up for a drive, check out Love Lane, 17.7km away, featuring charming shops and a family-friendly atmosphere.

Recreation

Enjoy the serene atmosphere at Cedar Point County Park, perfect for relaxation and nature walks. For some fun, head to Shelter Island Whale's Tail for a mini-golf adventure with family. Don’t miss Bay Street Theatre for a captivating performance, blending culture and entertainment in a romantic setting.

Adventure

Experience the Greenport Carousel, a charming ride offering outdoor family fun located 4.8km away. For a thrilling day, head to Splish Splash Water Park, 24.8km from Shelter Island, where adventure and entertainment await. Enjoy arcade games and excitement at Stay and Play LLC, located 25.7km away.

Nightlife

Shelter Island offers a charming nightlife scene. Start your evening at the lively Sunset Beach for cocktails with a view. For a more laid-back vibe, visit The Chequit, where you can enjoy local brews and live music, creating a perfect blend of relaxation and entertainment.

Find the best attractions near Shelter Island

Explore the charm of Shelter Island, perfect for outdoor adventures and romantic beach getaways. Discover beautiful spots like Crescent Beach and Hay Beach, along with local parks and historic buildings that offer a cultural experience for families and travelers alike. Whether you're seeking relaxation by the shore or exploring the island's rich history, Shelter Island has something for everyone to enjoy.

• Crescent Beach: Experience the serene beauty of Crescent Beach, located 3.2km from Shelter Island. With its soft sands and gentle waves, it's the perfect spot for beach vibes, sunbathing, swimming, or simply enjoying a peaceful stroll along the shore.
• Railroad Museum of Long Island: Just 4.8km away, immerse yourself in the rich history of railroads at this cultural gem. Explore fascinating exhibits, vintage train cars, and learn about the evolution of rail travel in the region, making it a must-visit for history enthusiasts.
• LongHouse Reserve: Located 14.5km from Shelter Island, this stunning sculpture garden offers a unique blend of art and nature. Wander through beautifully landscaped grounds filled with contemporary sculptures, perfect for families and outdoor lovers seeking inspiration and tranquility.

Best time to go to Shelter Island

The best time to visit Shelter Island is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

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

Tips to save on your trip to Shelter Island

• Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Shelter Island.
• Consider traveling to Shelter Island during the low season (January to March) for more affordable options.
• Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
• Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.