Shelter Island holiday lettings

We found 2,362 holiday rentals — enter your dates for availability

Discover a selection of 90 homes and other holiday rentals in Shelter Island that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a fireplace. No matter what you're looking for, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Shelter Island

Showing deals for:26 Jun - 3 Jul

Image gallery for Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Pool
10 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Orient

8% off
Price is £9,659
for 7 nights, 1 room
£1,380 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Shelter Island

  • Stunning beaches: Enjoy idyllic shores perfect for relaxation and romantic getaways, such as Silver Beach.
  • Outdoor activities: Explore nature with various outdoor pursuits, ideal for adventure seekers and tranquillity lovers alike.
  • Charming firepits: Experience cosy evenings under the stars around delightful firepits.
  • Historic charm: Discover Shelter Island's rich history through its beautiful architecture and local culture.
  • Variety of accommodations: Choose from charming cottages, private homes, and comfortable apartments for a memorable stay.

Popular types of accommodation in Shelter Island

You're off to Shelter Island, and the next step is selecting the perfect place to stay. Explore our top offerings for Shelter Island holiday rentals, including charming houses, quaint cottages, and comfortable apartments. Whether you're looking for a spacious house rental or a delightful holiday home, you'll find a variety of options to suit your needs and ensure a memorable getaway.

  • Houses: The top choice for holiday rentals in Shelter Island, ideal for groups or families seeking a home-away-from-home experience.
  • Cottages: A charming and cosy option, perfect for those wanting a quaint retreat amid the scenic beauty of Shelter Island.
  • Apartments: A convenient and flexible choice, offering a home-like atmosphere with easy access to local amenities.
  • Condos: A modern accommodation type that combines comfort and style, often located in vibrant areas.
  • Villas: Luxurious and spacious, these properties provide an upscale experience for a memorable getaway.**

Top attractions in and around Shelter Island

Shelter Island is perfect for outdoor and romantic getaways, with its stunning beaches, historic buildings, and urban parks. Visitors can immerse themselves in local culture while enjoying various activities, such as relaxing by the beach or exploring nature. Don't miss the charming firepit, ideal for cosy evenings under the stars. Whether you're seeking adventure or tranquillity, Shelter Island has something for every traveller.

  • 67 Steps Beach: A picturesque beach characterised by its sandy shores and scenic views. The 67 steps leading down to the beach provide a unique descent, offering a lovely spot for relaxation and sunbathing.
  • Sag Harbor Marine Park: This vibrant marina offers a blend of adventure and outdoor fun. Enjoy water sports, fishing, or simply soaking up the beach atmosphere while taking in stunning views of the harbour.
  • Gardiner's Bay Country Club: Nestled within Shelter Island, this charming golf course features beautifully manicured greens and a tranquil setting, perfect for both seasoned golfers and novices alike.

Things to do recommended for couples

For a romantic getaway on Shelter Island, indulge in wine tasting at Kontokosta Winery or Pindar Vineyards, both offering enchanting atmospheres. For a bit of fun, try your hand at mini golf at the Shelter Island Whale's Tail, perfect for some light-hearted competition and adventure together.

Things to do recommended for families

Families visiting Shelter Island can enjoy a delightful ride on the Greenport Carousel, just 1.9km away, and unwind at Cedar Point County Park and Goldsmith's Inlet Park, both offering fantastic relaxation vibes within a short distance, perfect for a memorable day out.

Things to do recommended for groups

Experience a captivating performance at Bay Street Theatre, just 3.1km from Shelter Island, or explore local produce at the Greenport Farmers' Market, located 1.9km away. For some outdoor fun, enjoy a round of golf at Noyac Golf Club, 3.7km from the island.

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

If you're travelling with a group, family, pets, or seeking longer stays, be sure to filter according to your key preferences. 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 features like a complete 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 important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions is wise.
  • 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, take a look at Vrbo accommodations that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that every member of the family feels comfortable and 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 spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. It might also be worth considering features such as a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Shelter Island

During your visit to Shelter Island, immerse yourself in its stunning scenery and delightful beaches, perfect for a romantic getaway or a family holiday. Explore nearby Fishers Island for a charming day excursion, or unwind at Silver Beach. Whether you're seeking budget-friendly options or simply want to relax, Shelter Island and its surroundings offer a captivating blend of historical charm and family-friendly activities, ensuring a memorable summer escape.

  • Hamptons: The Hamptons, located 5.6km from Shelter Island, is a renowned holiday destination famous for its stunning beaches and luxurious atmosphere. Visitors flock to this area for a romantic getaway or outdoor adventures, where you can bask in the sun on pristine sands or enjoy water sports. Golf enthusiasts will appreciate the numerous golf courses, while music lovers can attend lively concerts. With family-friendly beaches and picturesque lakes, the Hamptons seamlessly blend relaxation with excitement, making it a must-visit locale.
  • Greenport: Situated a mere 1.9km from Shelter Island, Greenport is a charming village that offers an enchanting seaside experience. Known for its outdoor activities and romantic setting, this destination is perfect for couples and families alike. Enjoy a leisurely stroll along the waterfront, explore local shops, or indulge in fresh seafood at one of the quaint restaurants. Greenport also hosts music concerts and events throughout the year, ensuring a vibrant atmosphere. With its inviting beaches and event conference venues, Greenport is a delightful place to explore.
  • Sag Harbor: Just 3.1km from Shelter Island, Sag Harbor is a picturesque town steeped in maritime history. Visitors come to enjoy its beautiful beaches and outdoor spaces, perfect for a romantic outing or family fun. Experience the thrill of skiing or relax in nearby parks while taking in the stunning coastal views. The area is dotted with golf courses for avid players, and the family-friendly beaches provide a perfect spot for relaxation. Sag Harbor’s blend of history, beachside charm, and recreational activities makes it an ideal destination for all.

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 simple

Are you hoping to cut costs on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. You may also enjoy considerable savings by booking a longer stay. To discover a Vrbo property that suits your budget, feel free to use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a handy platform for you to plan new adventures, resume your previous arrangements, or manage your travel itinerary. You can easily access properties you've saved or booked, organised into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.vrbo.com/en-gb/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)
  • Foster Memorial Town Beach (4.9 mi / 7.9 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 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.

Frequently asked questions

What is the best area to stay in Shelter Island when booking a holiday rental?
When considering a holiday rental in Shelter Island, a popular area to stay is near the Centre Island neighbourhood. This charming area offers a delightful blend of natural beauty and local amenities, making it an ideal base for your holiday. Visitors can enjoy the stunning landscapes and serene beaches, with nearby attractions including the picturesque Sunset Beach, which is great for watching the sun dip below the horizon, and the tranquil Mashomack Preserve, a haven for birdwatchers and nature enthusiasts alike.

Another appealing option is the area close to the historic Shelter Island Heights. This quaint neighbourhood features beautiful Victorian architecture and is within walking distance to the Shelter Island Country Club, where you can indulge in a round of golf. The Heights also offers easy access to the delightful shops and eateries that showcase local flavours.

Overall, Shelter Island boasts a variety of holiday rental properties, providing a range of options for different budgets and preferences.
How much does it cost to rent a holiday home in Shelter Island?
Prices for holiday 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 traveling 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. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Shelter Island holiday 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 areas near Crescent Beach and Hay Beach, where you'll find charming seaside properties with stunning views of the water. Many of these rentals come equipped with amenities such as spacious decks for outdoor dining, private gardens for relaxation, and fully equipped kitchens for self-catering. The proximity to the beach allows for easy access to swimming and sunbathing, making it ideal for families and groups.

Additionally, the area around the Shelter Island Yacht Club offers properties that cater to sailing enthusiasts, with amenities like boat docks and access to water sports. The nearby Sunset Beach area is also popular, featuring beach houses with outdoor fire pits and BBQ areas, superb for evening gatherings after a day on the beach.

For those interested in exploring the natural beauty of the island, many rentals are situated close to hiking trails and nature reserves, providing opportunities for outdoor activities.
What is the most popular type of holiday rental accomodation in Shelter Island?
In Shelter Island, holiday houses are the most popular type of holiday rental, with approximately 276 available throughout the area. These spacious homes often feature multiple bedrooms, large living areas, fully equipped kitchens, and outdoor spaces such as decks or patios, superb for enjoying the tranquil surroundings. Additionally, there are around 12 charming cottages, which provide a cozier alternative, often with quaint interiors and private outdoor areas. While there are several apartments available, they are less common compared to the abundance of holiday houses and cottages.
Are there any family house rentals in Shelter Island?
In Shelter Island, there are some family-friendly holiday rentals available, with around 44 options to choose from. This charming locale is great for families looking to enjoy a peaceful getaway. Many properties feature spacious living areas, fully equipped kitchens, and outdoor decks or patios for al fresco dining, making it easy to prepare meals and enjoy the fresh air. Visitors can often find amenities such as Wi-Fi and air conditioning to ensure a comfortable stay.

The island is known for its beautiful beaches, like Crescent Beach and Shell Beach, which are ideal for children to play and for families to relax by the water. Additionally, the nearby Mashomack Preserve offers nature trails and opportunities for wildlife watching, providing a wonderful setting for outdoor adventures.
Can I rent a holiday home with a pool or hot tub in Shelter Island?
In Shelter Island, there are plenty of holiday homes available for rent that feature pools and hot tubs, with around 27 options to choose from. This picturesque destination offers a tranquil escape, where you can enjoy the beauty of nature and the serenity of the surrounding waters. Properties can be found in various neighbourhoods across the island, providing diverse settings from waterfront views to more secluded retreats.

Travellers can expect a range of amenities in these rentals, including private swimming pools, relaxing hot tubs, outdoor dining areas, and fully equipped kitchens, making them superb for both relaxation and entertaining.
Can I find long-stay holiday rentals in Shelter Island?
A long-stay holiday 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, providing a welcoming environment for travellers with furry companions. The island offers a variety of charming properties that often feature amenities such as spacious gardens, outdoor patios, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a relaxing getaway. Many of these rentals are designed to ensure comfort, with features like air conditioning, Wi-Fi, and laundry facilities.

Shelter Island is known for its tranquil atmosphere and beautiful natural surroundings, with easy access to parks and beaches where pets are welcome. The nearby Mashomack Preserve offers lovely trails for walking and exploring, while local beaches provide opportunities for sunbathing and swimming. Additionally, the island boasts pet-friendly dining options, allowing you to enjoy meals with your pets by your side.
Are there any remote work holiday rentals in Shelter Island?
In Shelter Island, there are a substantial number of remote work-friendly holiday rentals available, specifically around 272 options. This picturesque destination offers a serene environment ideal for those looking to balance work and leisure. Many properties provide essential amenities for remote work, including dedicated desk spaces, comfortable chairs, and reliable Wi-Fi, ensuring a conducive work atmosphere.

Travellers can expect a variety of accommodations, ranging from charming cottages to spacious homes, often featuring inviting living areas and outdoor spaces where one can unwind after a long day of work. The tranquil surroundings, complemented by beautiful waterfront views and proximity to local parks, make it easy to take breaks and enjoy the natural beauty of the island.

Moreover, the nearby beaches and scenic walking trails offer great opportunities for relaxation and exploration during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Shelter Island holiday rentals with parking?
Vrbo offers a wide selection of holiday 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, popular holiday rental amenities include well-equipped kitchens, inviting decks or patios for outdoor relaxation, and cosy fireplaces that enhance the charm of the accommodations. Many rentals also feature on-site parking for convenience, making it easier for guests to explore the island. Additionally, some properties come with helpful appliances like blenders, superb for preparing meals or refreshing drinks.
When is the best time to visit Shelter Island for a holiday rental?
The best time to visit Shelter Island for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts visitors looking to enjoy the warm weather, sandy beaches, and a host of outdoor activities, including kayaking, cycling, and leisurely strolls along the picturesque shorelines. The island's charming atmosphere is great for families and couples alike, making it an ideal getaway destination.

During these summer months, temperatures typically range from 20 to 30 degrees Celsius, creating a comfortable environment for beachgoers and those keen on exploring the island's natural beauty. Outdoor dining options flourish, and local events often take place, allowing you to immerse yourself in the lively community spirit.

If you're seeking a more budget-friendly experience, consider planning your visit in November when the island is quieter, yet still offers the chance to savour its tranquil beauty. This time of year allows for peaceful walks and a chance to enjoy the local flora without the summer crowds.
How early should I book a Shelter Island holiday rental?
Book your Shelter Island holiday 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 holiday 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 discover a blend of natural beauty and quaint charm. One of the top attractions is the picturesque Mashomack Preserve, a stunning area for hiking and birdwatching, offering scenic trails that showcase the island's diverse ecosystems. Another popular site is the historic Shelter Island Lighthouse, which provides lovely views of the surrounding waters and is a great spot for photography.

For those interested in maritime activities, the area around Crescent Beach is ideal for swimming and sunbathing, while nearby Shell Beach is known for its tranquil atmosphere. The island also features several local vineyards that offer tastings and tours, allowing guests to explore the region's wine culture.

Additionally, visitors can enjoy the charming shops and restaurants in the centre of the island, where local seafood and farm-to-table dishes are highlights.
Can I change or cancel my Shelter Island home rental booking on Vrbo?
To find Shelter Island holiday 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 holiday 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 as applicable.

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.

More holiday ideas