Shelter Island vacation rentals

Why visit Shelter Island

1. Beautiful Beaches: Shelter Island boasts stunning beaches like Crescent Beach, perfect for sunbathing and swimming.
2. Outdoor Adventures: Explore scenic landscapes ideal for hiking, biking, and nature walks amidst the island's natural beauty.
3. Cultural Experiences: Enjoy local art galleries and historic buildings that reflect the island's rich heritage.
4. Relaxing Accommodations: Choose from cozy cottages to private beach houses for a comfortable stay.
5. Family-Friendly Activities: Discover vibrant communities offering fun excursions suitable for all ages.

Popular types of accommodation in Shelter Island

Discover the charm of Shelter Island with our selection of vacation rentals, including houses, cozy cottages, and modern apartments. Whether you're seeking a tranquil retreat or a fun-filled getaway, we have the perfect accommodation for you. Enjoy access to private beaches and explore the beauty of New York’s vacation rentals. Your ideal Shelter Island escape awaits!

• Houses: The top choice for visitors in Shelter Island, offering spacious and comfortable living for families, friends, or couples seeking a home-like experience.
• Cottages: A charming second option, these cozy accommodations provide a rustic atmosphere, perfect for a tranquil getaway.
• Apartments: Ideal for those wanting convenience, these rentals offer all the essentials for a comfortable stay in the heart of Shelter Island.
• Condos: A popular fourth choice, condos combine modern amenities with a community feel, great for both short and extended stays.
• Villas: Rounding out the list, these luxurious spaces provide an upscale experience, perfect for those looking to indulge.**

Top attractions in Shelter Island

Discover the charm of Shelter Island, New York, perfect for a romantic getaway or outdoor adventure. With stunning beaches, historic buildings, and urban parks, there's something for everyone. Whether you're seeking cultural experiences or simply looking to relax by the water, Shelter Island offers a delightful blend of activities to make your vacation memorable. Enjoy the beauty and tranquillity of this picturesque destination, ideal for families, couples, and solo travellers alike.

1. 67 Steps Beach: A picturesque beach located 6.4km from Shelter Island, 67 Steps Beach offers stunning views and a relaxing atmosphere, perfect for sunbathing and swimming.
2. Sag Harbor Marine Park: Situated 8.0km from Shelter Island, this marina is ideal for outdoor adventures, featuring beach access, water activities, and scenic spots for picnics.
3. Railroad Museum of Long Island: Located 4.8km away, this cultural gem showcases the history of railroads in the region, featuring exhibits and vintage trains to explore.

Things to do recommended for couples

For a romantic getaway on Shelter Island, visit Kontokosta Winery for its charming ambiance, enjoy a fun round at Shelter Island Whale's Tail mini-golf, or dine at Indian Wells Beach for a delightful meal with a view. These experiences promise unforgettable moments together!

Things to do recommended for families

Your family will love the Greenport Carousel, only 4.8km away, with its outdoor charm. For relaxation, visit Cedar Point County Park, 8.0km away, or Goldsmith's Inlet Park, 11.3km away, both offering serene vibes perfect for unwinding together.

Things to do recommended for groups

Groups visiting Shelter Island can enjoy a vibrant performance at Bay Street Theatre, explore local produce at the Greenport Farmers' Market, and unwind with a round of golf at Noyac Golf Club, all while soaking in the area's unique culture and outdoor charm.

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

If you're planning a trip with a group, family, or pets, or if you're interested in extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

• Traveling to Shelter Island with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and many more on Vrbo.
• Traveling to Shelter Island with young kids: Travelling with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities, like a private swimming 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 trip isn’t truly complete without their furry companions. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels at home.
• Planning for a long term stay visiting Shelter Island: If you’re in search of vacation rentals offering discounts for month-long stays, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features like parking, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Shelter Island

Discover the charm of Shelter Island, New York, perfect for outdoor enthusiasts and romantic getaways. Enjoy pristine beaches like Crescent Beach and explore the scenic landscapes that make this destination unique. Nearby, vibrant communities offer family-friendly excursions, local art, and a touch of luxury. Whether you seek a private beach house or a cozy retreat, Shelter Island promises an unforgettable vacation experience filled with history and natural beauty.

• Sag Harbor: Sag Harbor is a charming village located 8.0km away from Shelter Island, known for its rich maritime history and vibrant arts scene. Visitors are drawn to its picturesque waterfront, which offers beautiful views and ample opportunities for outdoor activities like sailing and kayaking. The area is perfect for romance, featuring quaint streets lined with boutiques, galleries, and delightful eateries. Local attractions include the family-friendly beaches and parks, ensuring a fun outing for visitors of all ages. Golf enthusiasts can enjoy a nearby golf course, while winter sports fans can seek out ski fields for some seasonal fun.
• Greenport: Just 4.8km from Shelter Island, Greenport is a delightful village renowned for its stunning waterfront and charming atmosphere. The village is a haven for outdoor lovers and romantics alike, boasting beautiful beaches and family-friendly spots. Greenport is also known for its vibrant local events, including music concerts and seasonal festivals. Visitors can try their luck at nearby casinos or enjoy a round of golf at local courses. With an inviting harbour and a variety of shops and restaurants, Greenport is an ideal spot for a leisurely day of exploration and relaxation.
• East Hampton: Located 17.7km from Shelter Island, East Hampton is a picturesque town that combines natural beauty with upscale amenities. Renowned for its stunning beaches and outdoor recreational areas, it’s a favourite destination for those seeking both adventure and relaxation. Visitors can enjoy a variety of activities, from skiing in winter to sunbathing in summer. The area is dotted with beautiful parks and family-friendly beaches, making it a perfect spot for picnics and outdoor fun. East Hampton also features a lively arts community and a range of dining options, ensuring a memorable experience for all who visit.

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 vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, make use of our filters to refine your search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's innovative Trip Board offers you a dedicated space to plan new trips, pick up right where you left off, or manage your travel arrangements. You can easily access properties you've saved or booked, now conveniently categorized under Potential, Upcoming, or Current Trips. To explore Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.