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Shelter Island holiday lettings

We found 2,337 holiday rentals — enter your dates for availability

Discover a selection of 85 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:6 Mar - 13 Mar

Image gallery for PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

Pool
10 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton, NY

7% off
Price is £7,188
for 7 nights, 1 home
£1,027 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

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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)
  • 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 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.

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, New York, the area of Crescent Beach is highly recommended. This charming neighbourhood offers an idyllic coastal atmosphere, making it superb for a relaxing getaway. The beach itself is picturesque and provides an excellent spot for swimming, sunbathing, and enjoying stunning sunsets over the water. Additionally, Crescent Beach is conveniently located near the Shelter Island Historical Society, which offers fascinating insights into the island's rich history and cultural heritage.

Another appealing choice is the area around the Shelter Island Country Club. This neighbourhood boasts a peaceful, rural setting with easy access to beautiful golf courses and scenic walking trails. The nearby Sylvester Manor Educational Farm is a highlight, where visitors can explore the grounds and learn about sustainable farming practices, all while enjoying the serene surroundings.
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, the areas around Crescent Beach and Shell Beach are particularly appealing. These locations offer picturesque views of the water and are ideal for those looking to unwind by the shore. Properties in these areas often come with amenities such as spacious decks for outdoor dining, private access to the beach, and well-equipped kitchens superb for self-catering.

Crescent Beach is known for its soft sands and calm waters, making it a great spot for families. Rentals here may include features like outdoor showers, fire pits, and access to kayaks or paddleboards, allowing guests to fully embrace the coastal lifestyle. Meanwhile, Shell Beach offers a more tranquil atmosphere and is close to the local shops and eateries in the village, which enhances the convenience for travellers.
What is the most popular type of holiday rental accomodation in Shelter Island?
In Shelter Island, holiday houses are the most popular type of accommodation, with around 66 available throughout the area. These spacious homes are great for families or groups and often feature multiple bedrooms, fully equipped kitchens, and private outdoor spaces for relaxing. Many are situated near picturesque spots such as Sunset Beach and the Mashomack Nature Preserve, allowing guests to enjoy the island's natural beauty. Additionally, there are several cottages and apartments available, which provide a cozier option for smaller parties or couples.
Are there any family house rentals in Shelter Island?
In Shelter Island, there are numerous family-friendly house rentals available, with around 44 options to choose from. The locale offers a peaceful retreat with plenty of space for families to enjoy. Many of these homes boast large living areas, fully equipped kitchens for preparing meals together, and outdoor spaces, superb for children to run around and play.

Visitors can find properties near popular attractions such as the picturesque beaches of Crescent Beach and Sunset Beach, both ideal for family outings. Some rentals even feature amenities like private pools, game rooms for entertainment, and outdoor patios for relaxing evenings under the stars.
Can I rent a holiday home with a pool or hot tub in Shelter Island?
In Shelter Island, there are several holiday homes available for rent that feature pools or hot tubs, with around 26 options to choose from. This picturesque destination offers a tranquil escape with beautiful waterfront views and a charming community atmosphere. Properties can be found in various neighbourhoods, including the serene Dering Harbor and the more bustling areas near Shelter Island Heights.
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 several pet-friendly house rentals available, ensuring a comfortable stay for travellers with pets. Many of these holiday homes are equipped with modern amenities, including fully stocked kitchens, outdoor spaces, and spacious living areas, providing a relaxing environment for families and groups.
Are there any remote work holiday rentals in Shelter Island?
In Shelter Island, there are a substantial number of remote work holiday rentals available, with approximately 63 options to choose from. This picturesque destination, located between the North and South Forks of Long Island, offers a tranquil environment ideal for working remotely. Many of the properties feature dedicated workspace amenities, including desks, Wi-Fi, and comfortable office chairs, ensuring that guests can maintain productivity while enjoying their surroundings. 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, holiday 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 holiday rental?
The best time to visit Shelter Island for a holiday rental is during the peak season from June to August, particularly in July when the island is bustling with energy and activity. This summer period is superb for travellers seeking a blend of relaxation and adventure, as the warm weather invites outdoor pursuits such as cycling, kayaking, and beachgoing.

Temperatures in July typically hover around the mid-20s Celsius, offering a delightful climate for exploring the island's beautiful beaches and scenic nature trails. This time of year also sees various local events and festivals, making it a vibrant choice for those who enjoy immersing themselves in the local culture and community.

If you're looking for a more tranquil experience, consider visiting in November, when you can enjoy the serene beauty of Shelter Island without the crowds. This time offers a peaceful retreat, superb for leisurely strolls along the shoreline or enjoying the picturesque autumn scenery.
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 enjoy a variety of attractions that highlight the island's natural beauty and charm. The Mashomack Preserve offers beautiful hiking trails and opportunities for birdwatching, making it a haven for nature lovers. Holiday rentals near this area provide easy access to the preserve's scenic landscapes.

Another gem is the picturesque Crescent Beach, where visitors can relax by the water and enjoy stunning sunsets. The nearby Shelter Island Historical Society features exhibits that delve into the island's rich history, and properties in this area often boast quaint, coastal decor.
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.

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