Shelter Island holiday homes

Why visit Shelter Island

• Scenic Beaches: Enjoy leisurely walks and relaxing moments on pristine beaches along the coast.
• Historic Heritage: Explore charming historic buildings and local heritage sites that echo the island’s rich past.
• Urban Parks: Stroll through picturesque urban parks perfect for family outings and romantic escapes.
• Outdoor Leisure: Embrace the relaxed island vibe with outdoor activities in nature-rich settings.
• Cultural Blend: Experience the unique mix of nature, culture, and luxury that makes every visit memorable.

Top attractions near Shelter Island

Shelter Island welcomes you with its beautiful beaches, charming urban parks, and historic buildings. Perfect for outdoor and romantic escapes, this unique city offers enriching experiences with a blend of culture and relaxation. Enjoy leisurely beach walks, explore local heritage sites, and indulge in the island’s relaxed vibe, making it a top destination for travellers seeking a mix of nature and history in a laid-back setting.

• East Hampton Main Beach: Located 19km from Shelter Island, this beach offers a relaxed coastal vibe with soft sands and refreshing ocean breezes, perfect for a leisurely day out.
• Sag Harbor Marine Park: Just 8km away, this marina blends adventure and outdoor fun with its beach vibes, ideal for water-based escapades and scenic strolls.
• Foster Memorial Town Beach: Equally 8km distant, this urban park delivers a city feel with family-friendly outdoor spaces, making it a vibrant locale for a day out.

Things to do recommended for couples

For a romantic getaway on Shelter Island, enjoy a sunset picnic at Crescent Beach or take a leisurely bike ride through the scenic trails. Don't miss a cozy dinner at a waterfront restaurant, where you can savour fresh seafood while watching the sun dip below the horizon.

Things to do recommended for families

Families visiting Shelter Island can enjoy a day at the picturesque beaches, explore the vibrant local parks, and take part in kayaking adventures. Don't miss the charming shops and eateries, perfect for a relaxing family outing.

Things to do recommended for groups

Explore the scenic beauty of Shelter Island by kayaking in the tranquil waters or join a guided bike tour to discover local wildlife. Enjoy a group picnic at Crescent Beach, soaking up the sun and stunning views while sharing stories with mates.

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 considering a longer stay, be sure to refine your search based on your key priorities. 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 amenities like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, 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 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, a family holiday isn’t truly finished without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly places 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 holiday rentals offering special rates 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

Explore the charm of Shelter Island, NY, where scenic coastal views meet rich history. Enjoy relaxing days on beautiful beaches, take leisurely strolls through family-friendly neighbourhoods, and immerse in a romantic, outdoor holiday experience. Discover the perfect blend of nature, culture, and luxury, making every moment memorable on this enchanting island.

• Hamptons: Situated 14km away from Shelter Island, Hamptons offers a splendid seaside escape with expansive beaches and outdoor pursuits. Visitors can enjoy a romantic stroll along the shore or engage in a round of golf at the local course. The area also features a ski field and opportunities for skiing during the winter months, adding a touch of seasonal excitement. Landmarks such as the family beach and a nearby lake provide scenic backdrops, making Hamptons a versatile destination for both relaxation and active adventures.
• Greenport: Just 5km from Shelter Island, Greenport is a charming city that beckons travellers with its outdoor allure and romantic ambience. The city is perfect for those who appreciate a blend of beachside leisure and cultural engagements. Enjoy a visit to the recreational area or catch a lively music concert, and spend leisurely days on the family beach or at the local park. With a range of outdoor activities and attractions, Greenport offers a delightful mix of relaxation and adventure.
• Sag Harbor: Located 8km from Shelter Island, Sag Harbor is a captivating city that provides an inviting mix of outdoor activities and beachside romance. Whether playing a round of golf or trying your hand at skiing, the area offers a variety of experiences. The local attractions, including a family beach and a scenic lake, enhance the natural beauty of the area. Sag Harbor is an excellent choice for travellers seeking both energising outdoor pursuits and tranquil moments by the sea.

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.

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

Booking with Vrbo is simple

Are you hoping to save some dollars on your next adventure? Being flexible with your travel dates can help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of holiday rental. We’re here to support you in finding the best options for your trip.

Vrbo Trips: Planning made easy

Vrbo’s forward-thinking Trip Board offers you a dedicated space to organise new adventures, pick up where you left off, or review and manage your plans. Any properties you’ve saved or booked before are now neatly arranged under Potential, Upcoming, or Current Trips. To access your Trip Boards, simply visit: https://www.bookabach.co.nz/trips

**Based on Vrbo properties bookings.

Scenic Shelter Island will entice you

The area's history and museums are just some of the reasons to come on holiday to Shelter Island. Travellers to this scenic city praise the island views, kayaking and parks. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Shelter Island

Are you searching for attractions to see in the area? Venture out of your holiday home and experience everything that makes Shelter Island a one-of-a-kind holiday spot. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

• Kontokosta Winery (3.5 mi / 5.7 km)
• Raphael Winery (6.8 mi / 10.9 km)
• Pindar Vineyards (7 mi / 11.3 km)
• Bedell Cellars (7.3 mi / 11.7 km)
• Peconic Bay Winery (8.1 mi / 13.1 km)
• Wolffer Estates Vineyard (9.1 mi / 14.6 km)

Exploring the natural features in Shelter Island

Whether you're an active traveller or just want to take in the scenery, Shelter Island is a great place to spend some time outside. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

• Sunset Beach (1.5 mi / 2.4 km)
• 67 Steps Beach (4 mi / 6.4 km)
• Orient Point County Park (8.1 mi / 13.1 km)
• LongHouse Reserve (9.4 mi / 15.1 km)
• The Hamptons Beaches (10 mi / 16.1 km)
• Georgica Beach (11.2 mi / 18.1 km)

How to get to and around Shelter Island

The nearest airport is in East Hampton, NY (HTO), located 8.8 mi (14.2 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away.