Shelter Island holiday rentals

We found 2,299 holiday rentals — enter your dates for availability
Discover a selection of 87 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:4 Dec - 11 Dec

Living area
Living area
Dining
Pool
Exceptional
(11 reviews)

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

Orient

8% off
S$15,588
for 7 nights, 1 room
S$2,227 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
The Harbor
Private kitchen
Dining Room
Patio
Exceptional
(99 reviews)

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

Sag Harbor

16% off
S$11,033
for 7 nights, 1 home
S$1,576 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
kitchen with large island and breakfast table
aerial view
master bedroom with balcony
view from living room towards pool, outdoor dining
Exceptional
(7 reviews)

Everything in Hamptons special discount available for weekly and monthly renters

Water Mill

17% off
S$76,176
for 7 nights, 1 home
S$10,882 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Exterior
Terrace/patio
Living area
Living area
Excellent
(10 reviews)

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

Water Mill

8% off
S$51,321
for 7 nights, 1 home
S$7,332 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Spacious Main Floor Living room
Exterior
Large Dining/Kitchen Space
Pool
Exceptional
(11 reviews)

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

Southold

8% off
S$12,233
for 7 nights, 1 home
S$1,748 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Living room w/ screen porch beyond
Pool
Front Porch
New Kitchen
Exceptional
(48 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
S$17,187
for 7 nights, 1 home
S$2,455 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Private kitchen
Pool area viewed from side with teak loungers and umbrellas
Main house dining area with wet bar, 300 bottle wine fridge and ice maker.
Covered porch on backside of main house
Exceptional
(7 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
S$44,871
for 7 nights, 1 home
S$6,410 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
Outdoor dining
Living area
Living area
Interior
Exceptional
(14 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
S$9,934
for 7 nights, 1 home
S$1,419 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Interior
Living area
Pool
Exceptional
(10 reviews)

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

Sag Harbor

8% off
S$13,374
for 7 nights, 1 cottage
S$1,911 per night
includes taxes & fees
Secluded Sag Harbor Cottage - HUGE pool and separate bungalow/pool house
Private kitchen
Dining
Outdoor dining
Room
Exceptional
(18 reviews)

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

Cutchogue

8% off
S$6,421
for 7 nights, 1 cottage
S$917 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Dining
Terrace/patio
Interior
Interior
Exceptional
(19 reviews)

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

Greenport

7% off
S$6,275
for 7 nights, 1 home
S$896 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Interior
Living area
Interior
Grill + outdoor dining / furniture to dine al fresco!
Exceptional
(42 reviews)

Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

Southold

7% off
S$7,788
for 7 nights, 1 home
S$1,113 per night
includes taxes & fees
Family and dog-friendly getaway near amazing wineries, beaches and restaurants!
Hall into sitting room
Master bed onto balcony
Kitchen from dining room
Dining room onto porch
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
S$13,044
for 7 nights, 1 home
S$1,863 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
View from entry foyer into double height living room, skylights, leading to pool
Thermador chefs kitchen with expansive island open to dining room & family room
Dining room seating 12 leading to chef's kitchen and doors leading to pool
Frankel Residence
Exceptional
(6 reviews)

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

Wainscott

8% off
S$21,678
for 7 nights, 1 home
S$3,097 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
From the bedroom
Facade
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Front yard closeup
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
S$7,154
for 7 nights, 1 cottage
S$1,022 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Guest house small private
outdoor seating area.
Living room, looking out toward Accabonac Harbor, water views.
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
Lovely seating in pool area for morning coffee.
Exceptional
(7 reviews)

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

East Hampton

8% off
S$21,345
for 7 nights, 1 home
S$3,049 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
Attention to details and fine workmanship was a sign of wealth both then and now
Every season brings special flower blooms
Our porch is furnished with plants for a Gilded Age feel
Second living room once called the "parlour"
Exceptional
(37 reviews)

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

Greenport

12% off
S$10,066
for 7 nights, 1 home
S$1,438 per night
includes taxes & fees
Historic Luxurious Captains Home- Greenport Village, wineries,golf, beach
Private kitchen
Outdoor dining
Pool
Living area
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
S$7,625
for 7 nights, 1 home
S$1,089 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
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
S$5,834
for 7 nights, 1 home
S$833 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Room
Private kitchen
Dining
Private kitchen
Exceptional
(14 reviews)

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

Southold

8% off
S$5,933
for 7 nights, 1 home
S$848 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Living area
Pool
Private kitchen
Terrace/patio
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
S$21,965
for 7 nights, 1 home
S$3,138 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Room
Property grounds
Exterior
Private kitchen
Exceptional
(8 reviews)

Waterfront Property on Shelter Island

Shelter Island

7% off
S$6,847
for 7 nights, 1 home
S$978 per night
includes taxes & fees
Waterfront Property on Shelter Island
Terrace/patio
Property grounds
Dining
Exterior
Exceptional
(5 reviews)

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

East Hampton

8% off
S$9,545
for 7 nights, 1 home
S$1,364 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
Room
Private kitchen
Terrace/patio
Living area
Exceptional
(10 reviews)

Springs Chic, Steps from private Gardiners Bay beach!

East Hampton

7% off
S$7,674
for 7 nights, 1 home
S$1,096 per night
includes taxes & fees
Springs Chic, Steps from private Gardiners Bay beach!
  • 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)
  • Crescent Beach (1.7 mi / 2.8 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)

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