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Shelter Island vacation rentals

We found 2,363 vacation rentals — enter your dates for availability

Discover a selection of 84 homes and other vacation rentals in Shelter Island that are perfect for your trip. Whether you’re staying in a vacation home with friends, family, or just with your pet, you'll have the amenities you expect and more, which might include WiFi and a fireplace. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Shelter Island

Showing deals for:Nov 14 - Nov 21

Image gallery for PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

Pool
10 out of 10 rating
Exceptional
(13 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton, NY

10% off
Price is CA $1,238
CA $12,426 total
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

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Find out more about Shelter Island

Find out more about Shelter Island

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 iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyHighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyLowAverage
November49.6°F (9.8°C)Light RainMostly SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowAverage

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.

**Based on Vrbo properties bookings.

Beautiful Shelter Island will entice you

The area's history and museums are just a few of the reasons to vacation in Shelter Island. Travelers to this scenic city praise the island views, kayaking and parks. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in and around Shelter Island

Are you hoping to find things to do in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that Shelter Island has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Kontokosta Winery (3.5 mi / 5.7 km)
  • Noyac Golf Club (6.1 mi / 9.7 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)

Exploring the natural features in Shelter Island

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Shelter Island is a great place to get out in nature. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city center:

  • Sunset Beach (1.5 mi / 2.4 km)
  • Crescent Beach (1.7 mi / 2.8 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)

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 center. If you can't find a flight that works for your travel itinerary, you could book a flight to Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away.

Frequently asked questions

What is the best area to stay in Shelter Island when booking a vacation rental?
When planning a vacation rental on Shelter Island, New York, the area of Silver Beach is highly recommended. This charming neighbourhood offers a peaceful atmosphere with beautiful sandy beaches and stunning waterfront views, making it an ideal spot for relaxation and recreation. Silver Beach is particularly appealing for families and couples looking to unwind by the water. The community boasts a selection of rental properties, often with direct beach access, ensuring a delightful stay.

Another fantastic option is the area around Crescent Beach. This picturesque locale is known for its stunning sunsets and tranquil waters, superb for swimming and kayaking. The proximity to the renowned Shelter Island Yacht Club adds a touch of elegance and provides opportunities for sailing enthusiasts. Visitors can enjoy the beautiful trails of the nearby Mashomack Preserve, where nature lovers can engage in the island's rich biodiversity.
How much does it cost to rent a vacation home in Shelter Island?
Prices for vacation rentals in Shelter Island vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Shelter Island to more spacious homes.
Are there any discounts for Shelter Island vacation house rentals?
You can find great discounts on house rentals in Shelter Island on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Shelter Island?
For renting a beach house in Shelter Island, consider the picturesque areas near Crescent Beach and Shell Beach. These locations offer a serene coastal atmosphere, with many vacation rentals just a short walk from sandy shores and stunning water views. Properties in this vicinity often feature amenities such as spacious outdoor decks, private gardens, and fully equipped kitchens, ideal for families or groups looking to enjoy a relaxing beach getaway.

In addition, the area around Havens Beach provides further options for travellers, where charming beach houses can be found located among lush greenery and offering easy access to the water. Many of these rentals come with outdoor showers, barbecue facilities, and comfortable living spaces, making them great for enjoying warm summer evenings by the beach.
What is the most popular type of vacation rental accomodation in Shelter Island?
In Shelter Island, vacation houses are the most popular rental option, with around 66 available across the island. These houses typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas for relaxation, making them ideal for families and larger groups. Additionally, there are several cottages and apartments, providing more compact and cosy alternatives for those seeking a quaint retreat. Most of these rentals are situated in tranquil neighbourhoods, allowing guests to enjoy the natural beauty of the area, including nearby beaches and parks.
Are there any family house rentals in Shelter Island?
In Shelter Island, there is a wide selection of family-friendly vacation rentals, with around 44 options available. The charming locale is great for families seeking a mix of relaxation and adventure. Many of these properties feature spacious living areas, fully equipped kitchens for preparing family meals, and comfortable bedrooms to ensure a restful stay. Outdoor spaces often include patios or decks, where families can enjoy al fresco dining or simply relax in the fresh air.

This area is known for its beautiful beaches, such as Crescent Beach and Wades Beach, which offer safe swimming and opportunities for picnicking. Additionally, families can explore nearby nature trails, parks, and recreational areas, great for hiking and outdoor activities. The local community also hosts various events throughout the year, providing a glimpse into the vibrant culture of Shelter Island.
Can I rent a vacation home with a pool or hot tub in Shelter Island?
In Shelter Island, there are plenty of vacation homes available for rent that come equipped with pools and hot tubs, with around 26 options to choose from. This picturesque destination offers a serene atmosphere, ideal for relaxation. Many of these properties are located near the waterfront, providing stunning views and easy access to the beach.
Can I find long-stay vacation rentals in Shelter Island?
A long-stay vacation rental in Shelter Island is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Shelter Island?
In Shelter Island, there are numerous pet-friendly house rentals available, with around 32 options to choose from. This charming destination offers a variety of vacation homes that cater to pet owners, often featuring amenities like spacious backyards, pet-friendly furnishings, and easy access to outdoor areas. Many of these properties come equipped with modern kitchens, comfortable living spaces, and outdoor patios, ideal for relaxing after a day of exploring.
Are there any remote work vacation rentals in Shelter Island?
In Shelter Island, there are numerous remote work vacation rentals available, with around 63 options to choose from. This picturesque destination offers a tranquil setting ideal for those looking to blend work and leisure. Many of the properties are well-equipped with essential amenities for remote work, including dedicated office spaces, desks, and reliable Wi-Fi, ensuring that you can stay productive during your stay. Additionally, some rentals may feature comfortable chairs, safe storage for your belongings, and even computer monitors for added convenience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Shelter Island vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Shelter Island with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Shelter Island?
In Shelter Island, vacation rentals commonly feature amenities that enhance comfort and convenience. Expect to find well-equipped kitchens, complete with refrigerators, microwaves, dishwashers, and essential cookware and utensils, allowing guests to prepare their own meals during their stay. These amenities cater to families and groups who prefer the flexibility of self-catering while enjoying the serene surroundings of the island.
When is the best time to visit Shelter Island for a vacation rental?
The most popular time to visit Shelter Island is during the summer months, specifically from June to August. This peak season draws vacationmakers eager to enjoy the island's beautiful beaches, charming boutiques, and vibrant local dining. With warm temperatures averaging around 25°C, it's ideal for outdoor activities like kayaking, cycling, and leisurely strolls along the waterfront.

July stands out as the most sought-after month, bustling with visitors who relish the lively atmosphere and the myriad of seasonal events. The island offers a plethora of opportunities for sightseeing and exploration, including the picturesque Mashomack Preserve, great for nature walks.

For those considering a more budget-friendly option, visiting in November can be quite rewarding. This shoulder month allows for a peaceful escape, where you can enjoy the island's autumnal beauty, with fewer crowds and a more relaxed pace. The tranquillity of the off-season creates an excellent environment for reflection and appreciation of Shelter Island's natural charm.
How early should I book a Shelter Island vacation rental?
Book your Shelter Island vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Shelter Island?
In Shelter Island, visitors can enjoy a variety of attractions that highlight the island's natural beauty and tranquil atmosphere. The Mashomack Preserve offers stunning walking trails and opportunities for wildlife viewing, making it a great spot for nature lovers. Vacation rentals in this area often provide easy access to the preserve's peaceful surroundings.

Another great attraction is Crescent Beach, where guests can relax on the sandy shores and take in lovely views of the water. Properties nearby typically offer a beachy charm and proximity to local amenities.
Can I change or cancel my Shelter Island home rental booking on Vrbo?
To find Shelter Island vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Shelter Island vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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