Shelter Island holiday lettings

Why visit Shelter Island

• Picturesque beaches: Shelter Island boasts stunning beaches ideal for sunbathing, swimming, and relaxing by the sea.
• Scenic nature trails: Explore the island's beautiful trails, perfect for hiking and enjoying the local wildlife.
• Charming parks: Visit tranquil parks that offer serene picnic spots and scenic views of the coastline.
• Historic landmarks: Discover the rich history of the island through its historic buildings and sites.
• Water activities: Enjoy a variety of water-based activities, including kayaking and sailing, for a fun-filled adventure.

Popular types of accommodation in Shelter Island

Discover the charm of Shelter Island, New York, where stunning natural beauty meets tranquil seaside living. Enjoy a variety of vacation rentals, from private homes to cosy cottages and apartments. Explore picturesque beaches, scenic trails, and local wildlife, or unwind with water activities and charming waterfront dining. Whether you’re seeking a summer getaway or a peaceful retreat, Shelter Island offers an idyllic escape for every type of traveller.

• Houses: These spacious and well-appointed homes offer a perfect retreat, ideal for families or groups looking for comfort and privacy during their stay on Shelter Island.
• Cottages: Quaint and charming, cottages provide a delightful escape, perfect for couples or small families wanting a homely feel amidst beautiful surroundings.
• Apartments: Convenient and often centrally located, apartments are a popular option for those seeking a more urban experience while enjoying the island's amenities.
• Condos: Offering a blend of space and luxury, condos are ideal for those looking for resort-like facilities combined with the comforts of home.
• Villas: For a touch of elegance, villas provide a lavish setting with stunning views, perfect for a luxurious getaway.**

Top attractions in and around Shelter Island

Shelter Island, New York, is a picturesque destination perfect for outdoor and romantic beach getaways. Visitors can explore beautiful beaches, charming parks, and historic buildings, all offering a unique blend of culture and natural beauty. The island caters to those seeking relaxation and adventure, making it an ideal spot for solo travellers, couples, or families looking to unwind and enjoy the scenic surroundings.

• Gardiner's Bay Country Club: This picturesque golf course offers stunning views of Gardiner's Bay, with meticulously maintained greens and fairways. It's a perfect spot for both seasoned golfers and beginners looking to enjoy a round in a serene setting.
• Mashomack Preserve: A beautiful urban park featuring lush landscapes and diverse wildlife. Ideal for family outings, this preserve offers trails for hiking, birdwatching, and immersing yourself in nature, all while enjoying the peaceful surroundings of Shelter Island.

Things to do recommended for couples

Embark on a scenic bike ride around Shelter Island, taking in the stunning waterfront views. Enjoy a candlelit dinner at a charming eatery, followed by a leisurely stroll along the beach at sunset, creating unforgettable memories together in this idyllic setting.

Things to do recommended for families

Families visiting Shelter Island can explore the beautiful beaches, enjoy a bike ride along the scenic trails, and take part in fun activities at the Shelter Island Historical Society. Don’t miss the chance to spot wildlife at the Mashomack Preserve for an unforgettable day together.

Things to do recommended for groups

Groups visiting Shelter Island can indulge in a delightful wine tasting at local vineyards and embark on a scenic bike ride around the charming coastal paths. Don't miss the opportunity to enjoy a group kayak tour to explore the serene waters and beautiful shorelines.

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

If you’re planning a trip with friends, family, pets, or considering an extended stay, be sure to refine your search according to your key priorities. Here are some helpful booking tips for Vrbo.

• Traveling to Shelter Island with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped 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 essential to prioritise their comfort and safety, along with 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 wouldn’t feel complete without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds to ensure that everyone feels 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 place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Shelter Island

Discover the enchanting charm of Shelter Island, New York, a perfect getaway for outdoor enthusiasts and romantic souls alike. From its picturesque beaches to scenic nature trails, the island offers a delightful blend of relaxation and adventure. Explore historical landmarks, enjoy family-friendly excursions, and immerse yourself in the stunning coastal scenery. Whether you seek a luxurious retreat or a budget-friendly escape, Shelter Island promises an unforgettable vacation experience.

• Hamptons: The Hamptons, located a mere 14km from Shelter Island, is a quintessential summer retreat renowned for its sandy beaches and charming villages. This region offers a romantic escape with a myriad of outdoor activities, including scenic golf courses and picturesque beach walks. Visitors can indulge in the local culture at art galleries and boutique shops, or relax on the family-friendly beaches. With its stunning coastal views and vibrant nightlife, the Hamptons provide an ideal getaway for couples and families alike.
• Greenport: Just 5km from Shelter Island, Greenport is a delightful waterfront village that captures the essence of coastal living. Known for its romantic outdoor spaces, Greenport boasts beautiful beaches and parks perfect for leisurely strolls. The local scene is lively, featuring music concerts and recreational areas that invite exploration. Visitors can enjoy fresh seafood at local restaurants or take a charming boat ride in the bay, making Greenport a must-visit for those seeking a laid-back yet engaging experience.
• Sag Harbor: Nestled 8km from Shelter Island, Sag Harbor is a historic whaling village that offers a unique blend of outdoor adventures and beach relaxation. This quaint town is perfect for romantic getaways, with inviting beaches and serene lakeside views. Golf enthusiasts will appreciate the nearby courses, while the vibrant arts scene promises a rich cultural experience. Stroll through the charming streets lined with shops and eateries, or enjoy a refreshing day at the beach, making Sag Harbor a delightful destination for every traveller.

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 save on your next getaway? Being flexible with your travel dates can often lead to significant savings, as prices can vary. Additionally, opting for a longer stay typically allows for greater discounts. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a dedicated space where you can plan new adventures, refine your existing itineraries, or manage your bookings with ease. The properties you’ve saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.