Shelter Island holiday rentals

We found 2,269 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:25 Dec - 1 Jan

Living area
Living area
Dining
Exterior
Exceptional
(12 reviews)

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

Orient

8% off
S$15,572
for 7 nights, 1 room
S$2,225 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
The Harbor
Private kitchen
Exterior
Patio
Exceptional
(103 reviews)

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

Sag Harbor

16% off
S$10,816
for 7 nights, 1 home
S$1,545 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Living area
Terrace/patio
Exterior
Pool
Excellent
(10 reviews)

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

Water Mill

8% off
S$50,546
for 7 nights, 1 home
S$7,221 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
living room
aerial view
master bedroom with balcony
kitchen with large island and breakfast table
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
S$74,807
for 7 nights, 1 home
S$10,687 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Dining Room with seating for Ten
Pool
Outdoor dining
Exterior
Exceptional
(28 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
S$11,102
for 7 nights, 1 home
S$1,586 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Large Dining/Kitchen Space
Exterior
Exterior
Spacious Main Floor Living room
Exceptional
(11 reviews)

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

Southold

8% off
S$16,398
for 7 nights, 1 home
S$2,343 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Hall into sitting room
Master bed onto balcony
Dining room from kitchen
Kitchen from dining room
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
S$17,403
for 7 nights, 1 home
S$2,486 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Interior
Terrace/patio
Private kitchen
Interior
Exceptional
(20 reviews)

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

Greenport

7% off
S$6,303
for 7 nights, 1 home
S$900 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Den
Pool
Front Porch
New Kitchen
Exceptional
(48 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
S$17,007
for 7 nights, 1 home
S$2,430 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Interior
Living area
Living area
Pool
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
S$9,972
for 7 nights, 1 home
S$1,425 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Living area
Exterior detail
Pool
Exceptional
(11 reviews)

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

Sag Harbor

8% off
S$13,195
for 7 nights, 1 cottage
S$1,885 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
S$6,556
for 7 nights, 1 cottage
S$937 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
The front walkway
A view of the house and pool from the creek, looking south
The front porch
The front of the house
Exceptional
(21 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
S$5,860
for 7 nights, 1 home
S$837 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Attention to details and fine workmanship was a sign of wealth both then and now
Every season brings special flower blooms
Second living room once called the "parlour"
Morning breakfast room
Exceptional
(37 reviews)

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

Greenport

12% off
S$10,110
for 7 nights, 1 home
S$1,444 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Exterior
Kitchen
Shed
Living Room
Exceptional
(108 reviews)

Relax in this light-filled home, steps from the beach and a short walk to town!

Greenport

8% off
S$8,190
for 7 nights, 1 home
S$1,170 per night
includes taxes & fees
Relax in this light-filled home, steps from the beach and a short walk to town!
Open entry foyer with wall of windowed doors to Zen Garden
Thermador chefs kitchen with expansive island open to dining room & family room
View from entry foyer into double height living room, skylights, leading to pool
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Exceptional
(6 reviews)

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

Wainscott

8% off
S$21,441
for 7 nights, 1 home
S$3,063 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
Living room, looking out toward Accabonac Harbor, water views.
Guest house small private
outdoor seating area.
Bar area pass-through to kitchen, with bar seating.
Exceptional
(7 reviews)

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

East Hampton

8% off
S$21,481
for 7 nights, 1 home
S$3,069 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
Front yard closeup
Facade
Living/dining space
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Exceptional
(23 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
S$6,998
for 7 nights, 1 cottage
S$1,000 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Property grounds
Private kitchen
Dining
Private kitchen
Exceptional
(14 reviews)

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

Southold

7% off
S$6,059
for 7 nights, 1 home
S$866 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Dining
Pool
Private kitchen
Living area
Wonderful
(18 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

7% off
S$22,116
for 7 nights, 1 home
S$3,159 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Dining
Property grounds
Terrace/patio
Private kitchen
Exceptional
(5 reviews)

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

East Hampton

8% off
S$9,565
for 7 nights, 1 home
S$1,366 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
Exterior
Property grounds
Interior
Pool
Exceptional
(90 reviews)

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

Greenport

8% off
S$4,508
for 7 nights, 1 apartment
S$644 per night
includes taxes & fees
Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views
Dining
Terrace/patio
Living area
Living area
Exceptional
(8 reviews)

North Fork Waterfront Gem

East Marion

6% off
S$7,970
for 7 nights, 1 home
S$1,139 per night
includes taxes & fees
North Fork Waterfront Gem
Lounge by the pool in total privacy
Dine in style overlooking the pool and grounds
New, professional grade, stainless steel appliances including Bertazzoni range
Primary bedroom w/California king, vaulted ceilings, tv, & private bathroom
Exceptional
(32 reviews)

Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village

East Hampton

15% off
S$9,068
for 7 nights, 1 home
S$1,295 per night
includes taxes & fees
Stylish East Hampton Village Retreat- Heated Pool and Sauna, Steps to Village
  • 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)
  • 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)
  • Havens Beach (5.5 mi / 8.8 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?
Among the most sought-after areas for a Shelter Island holiday home is Dering Harbour. When you book your Vrbo holiday property, you'll have the whole place to yourself. This means you don't have to share it with anyone apart from your people.
What is the most popular type of holiday rental accommodation in Shelter Island?
According to our research, houses are the most desirable property type in Shelter Island. But having said that, everyone's idea of the perfect stay isn't going to be the same. Vrbo has holiday homes with every size, shape and budget in mind, so you're sure to find the best fit for your needs.
How much does it cost to rent a holiday rental in Shelter Island?
Length of stay, property type and time of year are among the factors that can influence the price of a holiday home. Simply add your travel dates to find your ideal escape. From cosy chalets to sprawling luxury villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Shelter Island?
When you travel and the style and size of the property will influence how much you'll pay for your beachside escape. Enter your Shelter Island travel dates to view your options on Vrbo. Did someone just say "hot tub"? Use our filters to select the features and amenities you need.
What are popular rental amenities in Shelter Island?
A lake view, a swimming pool and nearby museums head the list of most popular rental amenities in Shelter Island. Whether you're taking to the road on your own, with a partner or a group of dear friends, Vrbo will help you find a holiday rental that suits your style with all the conveniences you're looking for.
What are the top attractions for families in Shelter Island?
Keep the kids busy at these fabulous family-friendly attractions in Shelter Island:
  • 67 Steps Beach
  • Orient Beach State Park
  • Railroad Museum of Long Island
Can I find two-bedroom holiday rentals in Shelter Island?
Gather your besties and enjoy peace, privacy and comfort in one of the five two-bedroom holiday rentals Shelter Island has to offer.
Are there holiday rentals with WiFi in Shelter Island?
Shelter Island has 27 holiday rentals with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to catching up on social media, these Vrbo homes make it easy to get online.
How old do you have to be to rent a holiday rental in Shelter Island?
The minimum required age is typically 16, 18 or 21. It can differ between properties on Vrbo, so look at the rules of your preferred Shelter Island holiday home before booking.
How long can I rent a holiday rental in Shelter Island for?
The amount of time you can book a Shelter Island holiday home for depends on each property. Simply enter your travel dates to find available options that offer long-term stays. They come with all you require to make your extended holiday more convenient and comfortable, such as air conditioning and kitchens. Some holiday rentals may also offer weekly or monthly discounts, so you can have a longer stay for less.

More holiday ideas