Shelter Island holiday rentals

We found 2,280 holiday rentals — enter your dates for availability
Discover a selection of 86 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:18 Dec - 25 Dec

Pool
Living area
Exterior
Living area
Exceptional
(12 reviews)

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

Orient

8% off
AU$17,025
for 7 nights, 1 room
AU$2,432 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Patio
Private kitchen
The Harbor
Dining Room
Exceptional
(102 reviews)

Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town

Sag Harbor

16% off
AU$11,933
for 7 nights, 1 home
AU$1,705 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
view from living room towards pool, outdoor dining
aerial view
kitchen with large island and breakfast table
master bedroom with balcony
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

16% off
AU$84,866
for 7 nights, 1 home
AU$12,124 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Living area
Terrace/patio
Exterior
Living area
Excellent
(10 reviews)

Stunning fall sunsets, coveted location on Mecox Bay - recently furnished

Water Mill

8% off
AU$54,535
for 7 nights, 1 home
AU$7,791 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Master bedroom with ensuite bathroom
Pool
Dining Room with seating for Ten
Exterior
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
AU$12,057
for 7 nights, 1 home
AU$1,722 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Den
Pool
Front Porch
Living room w/ screen porch beyond
Exceptional
(48 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
AU$18,699
for 7 nights, 1 home
AU$2,671 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Covered porch on backside of main house
Pool area viewed from side with teak loungers and umbrellas
Main house living room
Private kitchen
Exceptional
(7 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
AU$47,661
for 7 nights, 1 home
AU$6,809 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
Pool
Living area
Interior
Outdoor dining
Exceptional
(14 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

8% off
AU$10,653
for 7 nights, 1 home
AU$1,522 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Hall into sitting room
Master bed onto balcony
Dining room onto porch
Kitchen from dining room
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
AU$19,100
for 7 nights, 1 home
AU$2,729 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Exterior
Exterior
Large Dining/Kitchen Space
Spacious Main Floor Living room
Exceptional
(11 reviews)

New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!

Southold

8% off
AU$12,830
for 7 nights, 1 home
AU$1,833 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Exterior detail
Living area
Interior
Exceptional
(10 reviews)

Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house

Sag Harbor

8% off
AU$14,430
for 7 nights, 1 cottage
AU$2,061 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Private kitchen
Dining
Outdoor dining
Living area
Exceptional
(18 reviews)

Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe

Cutchogue

8% off
AU$6,937
for 7 nights, 1 cottage
AU$991 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Front yard closeup
Facade
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Living/dining space
Exceptional
(23 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
AU$7,638
for 7 nights, 1 cottage
AU$1,091 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Interior
Terrace/patio
Dining
Interior
Exceptional
(19 reviews)

Entire, new, roomy, village beach house close to beach, park, and town center

Greenport

8% off
AU$6,715
for 7 nights, 1 home
AU$959 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
The kitchen is all glass with a spectacular view of the pool and creek
A view of the house and pool from the creek, looking south
The front of the house
The front walkway
Exceptional
(20 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
AU$6,243
for 7 nights, 1 home
AU$892 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Terrace/patio
Pool
Private kitchen
Dining
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
AU$23,092
for 7 nights, 1 home
AU$3,299 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Bar area pass-through to kitchen, with bar seating.
Living room, looking out toward Accabonac Harbor, water views.
Lovely seating in pool area for morning coffee.
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
Exceptional
(7 reviews)

WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!

East Hampton

8% off
AU$22,440
for 7 nights, 1 home
AU$3,206 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
Private kitchen
Property grounds
Dining
Exterior
Exceptional
(5 reviews)

Beautiful 4 bedroom house with tranquil gardens close to bay beaches.

East Hampton

8% off
AU$10,239
for 7 nights, 1 home
AU$1,463 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
Private kitchen
Private kitchen
Room
Dining
Exceptional
(14 reviews)

Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country

Southold

8% off
AU$6,409
for 7 nights, 1 home
AU$916 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Morning breakfast room
Every season brings special flower blooms
Our porch is furnished with plants for a Gilded Age feel
Attention to details and fine workmanship was a sign of wealth both then and now
Exceptional
(37 reviews)

Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach

Greenport

12% off
AU$10,943
for 7 nights, 1 home
AU$1,563 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Thermador chefs kitchen with expansive island open to dining room & family room
Frankel Residence
Open entry foyer with wall of windowed doors to Zen Garden
Exceptional
(6 reviews)

Completely Renovated Home on ~2 Private Acres, Near Beach/Town

Wainscott

8% off
AU$23,127
for 7 nights, 1 home
AU$3,304 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Backyard Water View
Kitchen
Exterior
Living Room
Exceptional
(6 reviews)

Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach

New Suffolk

8% off
AU$4,820
for 7 nights, 1 home
AU$689 per night
includes taxes & fees
Charming 2 bedroom house in Quaint New Suffolk -short walk to New suffolk Beach
Pool
Dining
Living area
Private kitchen
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
AU$41,640
for 7 nights, 1 home
AU$5,949 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
Living area
Living area
Dining
Room
Exceptional
(9 reviews)

Modern Home in East Hampton great for a summer or winter retreat.

East Hampton

7% off
AU$7,722
for 7 nights, 1 home
AU$1,103 per night
includes taxes & fees
Modern Home in East Hampton great for a summer or winter retreat.

  • 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, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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)
  • 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 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, 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Shelter Island holiday homes prices shown on Stayz?
Stayz 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.
Are there any Shelter Island holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Shelter Island holiday homes?
You can find great discounts on holiday homes in Shelter Island on Stayz, 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.
Can I change or cancel my Shelter Island holiday home booking on Stayz?
To find Shelter Island holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Shelter Island?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Shelter Island holiday home?
Book your Shelter Island holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Shelter Island?
Prices for holiday homes 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. Stayz offers something for every taste and budget, from affordable homes in Shelter Island to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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