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Shelter Island vacation rentals

We found 2,340 vacation rentals — enter your dates for availability

Discover a selection of 85 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:Mar 6 - Mar 13

Image gallery for Charming East Hampton cottage w/pool, near Georgica beach

pool, loungers, outdoor dining, house
10 out of 10, Exceptional, (91 reviews)
Exceptional
(91 reviews)

Charming East Hampton cottage w/pool, near Georgica beach

East Hampton, NY

10% off
Price is CA $1,006
CA $9,262 total
includes taxes & fees
Charming East Hampton cottage w/pool, near Georgica beach

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Find out more about Shelter Island

Why visit Shelter Island

  • Stunning beaches: Relax on beautiful shores, perfect for a romantic getaway and outdoor fun.
  • Outdoor activities: Enjoy kayaking and exploring picturesque parks, ideal for adventure enthusiasts.
  • Rich history: Discover local historic sites that showcase the unique culture of Shelter Island.
  • Family-friendly neighbourhoods: Explore charming areas like Shelter Island Heights, great for all ages.
  • Cozy accommodations: Choose from private homes, quaint cottages, and modern apartments for a comfortable stay.

Popular types of accommodation in Shelter Island

Planning a getaway to Shelter Island? You're in for a treat. With a variety of cozy accommodations, including houses, charming cottages, and modern apartments, you'll find the perfect spot to relax. Explore our selection of Shelter Island vacation rentals and enjoy transparency, savings, and peace of mind on your holiday. Make your stay unforgettable with the ideal vacation rental in Shelter Island.

  • Houses: The top choice for visitors, these spacious residences offer a home-like atmosphere, ideal for families or groups seeking comfort and privacy.
  • Cottages: A close second, these quaint and cozy retreats provide a charming escape for couples or small families.
  • Apartments: Offering convenience in prime locations, these units are perfect for those looking for a more urban experience.
  • Condos: These modern accommodations often come with shared amenities, great for those wanting a resort-like experience.
  • Villas: Elegant and luxurious, villas are perfect for a lavish getaway with stunning views and ample space.**

Top attractions in and around Shelter Island

For a romantic and adventurous getaway, Shelter Island, New York, offers stunning beaches and historic sites perfect for outdoor enthusiasts. Visitors can explore the local beaches, enjoy kayaking, and relax in picturesque urban parks. With a blend of culture and natural beauty, Shelter Island invites travellers to immerse themselves in its serene environment while enjoying various attractions and activities.

  • 67 Steps Beach: A picturesque beach approximately 6.4km from Shelter Island, known for its tranquil atmosphere and scenic views. Enjoy the soft sand, gentle waves, and perfect beach vibes, making it an ideal spot for relaxation and sunbathing.
  • Gardiner's Bay Country Club: Nestled within Shelter Island, this exclusive golf course offers a challenging layout amid stunning natural beauty. Experience a round of golf surrounded by lush greenery and scenic vistas, perfect for golf enthusiasts.
  • Orient Point County Park: Located 12.9km away, this urban park is perfect for families and outdoor enthusiasts. With walking trails, picnic areas, and beautiful waterfront views, it offers a great escape for a day of exploration and relaxation.

Things to do recommended for couples

For a romantic getaway on Shelter Island, visit Kontokosta Winery for a charming wine experience, or enjoy a fun round of mini-golf at Shelter Island Whale's Tail. Don't miss Osprey's Dominion Winery for more delightful wine tastings in a lovely setting.

Things to do recommended for families

Families can explore Cedar Point County Park for relaxation, visit Goldsmith's Inlet Park for a serene atmosphere, and enjoy the charming Greenport Carousel, perfect for outdoor fun, all within a short drive from Shelter Island.

Things to do recommended for groups

Immerse yourselves in local culture at the Greenport Farmers' Market, only 4.8km away, or enjoy a captivating show at Bay Street Theatre, 8.0km from Shelter Island. For outdoor fun, challenge each other at Noyac Golf Club, located 9.7km away.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, it’s important to prioritize your filters accordingly. 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, as well as features like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for 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 prioritize their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, it's wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Shelter Island: For many, a family getaway isn’t truly fulfilling without their furry companion by their side. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Shelter Island: If you're in search of vacation rentals that offer special rates for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Shelter Island

Discover the charm of Shelter Island, New York, where outdoor adventures and romantic beach getaways await. Experience stunning scenery and rich history while exploring family-friendly neighborhoods like Shelter Island Heights. Whether you're seeking budget-friendly excursions or a relaxing retreat, this picturesque destination offers the perfect escape. From its beautiful shores to delightful local vibes, Shelter Island promises a memorable vacation experience for every traveller.

  • Hamptons: The Hamptons, located 14.5km from Shelter Island, is a quintessential summer getaway known for its stunning beaches and upscale charm. This area offers a romantic atmosphere with plenty of outdoor activities such as golfing and beach lounging. Visitors can enjoy live music concerts and unwind at luxurious resorts, making it a perfect destination for couples and families alike. Local attractions include beautiful sandy beaches and tranquil lakes, providing a serene backdrop for relaxation and recreation.
  • Greenport: Just 4.8km from Shelter Island, Greenport is a charming village that beckons with its picturesque waterfront and vibrant community. This destination is ideal for those seeking outdoor adventures, romantic strolls, and beach time. Enjoy activities like golfing or attending lively music concerts, while the nearby family-friendly beaches provide a great spot for sunbathing and swimming. Greenport also features event conference venues, making it a versatile stop for both leisure and business travelers.
  • Sag Harbor: Located 8.0km away from Shelter Island, Sag Harbor is a historic town that beautifully combines outdoor leisure with coastal charm. Visitors can indulge in beach activities or explore the local parks, making it a perfect choice for those who appreciate nature and relaxation. Popular attractions include golf courses and ski fields, catering to a variety of interests. This picturesque village, with its quaint streets and inviting atmosphere, is ideal for romantic getaways and family outings.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Looking to save on your next adventure? Consider being flexible with your travel dates, as this can lead to significant price differences. Also, booking a longer stay can often result in excellent savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board is designed to help you manage your travel plans effortlessly. It provides a convenient space to create new trips, continue planning, or review and organize your existing bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To discover more about 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)
  • The Old Field Vineyards (3.7 mi / 6 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)
  • 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 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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right.If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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