Shelter Island holiday rentals

We found 2,253 holiday rentals — enter your dates for availability
Select from 87 homes, 10 cottages and other holiday rentals in Shelter Island to find one that's 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:15 Jan - 22 Jan

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$76,377
for 7 nights, 1 home
S$10,911 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
Living area
Terrace/patio
Pool
Exterior
Excellent
(10 reviews)

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

Water Mill

8% off
S$50,061
for 7 nights, 1 home
S$7,152 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Outdoor dining
Dining
Pool
Living area
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

25% off
S$40,368
for 7 nights, 1 home
S$5,767 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
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.
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$21,563
for 7 nights, 1 home
S$3,080 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
Frankel Residence
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
View from entry foyer into double height living room, skylights, leading to pool
Exceptional
(6 reviews)

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

Wainscott

7% off
S$22,423
for 7 nights, 1 home
S$3,203 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Living area
Pool
Dining
Terrace/patio
Wonderful
(20 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

7% off
S$22,209
for 7 nights, 1 home
S$3,173 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Pool
Living area
Outdoor dining
Interior
Exceptional
(15 reviews)

PERFECT GETAWAY East Hampton / Sag Harbor

East Hampton

7% off
S$9,966
for 7 nights, 1 home
S$1,424 per night
includes taxes & fees
PERFECT GETAWAY East Hampton / Sag Harbor
Exterior
Outdoor dining
Property grounds
Dining
Exceptional
(22 reviews)

The Lane House | Private Beach Escape

Orient

16% off
S$6,181
for 7 nights, 1 home
S$883 per night
includes taxes & fees
The Lane House | Private Beach Escape
The Harbor
Private kitchen
Exterior
Dining Room
Exceptional
(104 reviews)

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

Sag Harbor

15% off
S$11,171
for 7 nights, 1 home
S$1,596 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Exterior
Property grounds
Dining
Private kitchen
Exceptional
(5 reviews)

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

East Hampton

8% off
S$9,558
for 7 nights, 1 home
S$1,365 per night
includes taxes & fees
Beautiful 4 bedroom house with tranquil gardens close to bay beaches.
Interior
Dining
Main living room and dining room
Interior
Exceptional
(29 reviews)

9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub

Sag Harbor

7% off
S$18,355
for 7 nights, 1 home
S$2,622 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Spacious Main Floor Living room
Exterior
Large Dining/Kitchen Space
Pool
Exceptional
(12 reviews)

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

Southold

7% off
S$11,785
for 7 nights, 1 home
S$1,684 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
view of pool
seating area rear deck
dining area, expandable table
Private kitchen
Exceptional
(15 reviews)

Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach

Water Mill

7% off
S$22,338
for 7 nights, 1 home
S$3,191 per night
includes taxes & fees
Sunsets Sweeping Farmland Views, Great Retreat Minutes from Flying Point Beach
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 walkway
The front of the house
Exceptional
(21 reviews)

Unique Southold waterfront luxury home with heated pool on Long Creek

Southold

7% off
S$5,823
for 7 nights, 1 home
S$832 per night
includes taxes & fees
Unique Southold waterfront luxury home with heated pool on Long Creek
Dining Room with seating for Ten
Pool
Outdoor dining
Exterior
Exceptional
(29 reviews)

Spacious New 4 Bedroom Home With Pool on 2 Acre Property

Peconic

8% off
S$11,155
for 7 nights, 1 home
S$1,594 per night
includes taxes & fees
Spacious New 4 Bedroom Home With Pool on 2 Acre Property
Sunlit living room with wide sliding glass doors that lead out to sundeck.
Swim in the solar heated pool or basque in the sun...
Fireplace with expansive hearth
Bright living room with stylish, mid-century modern furnishings
Exceptional
(10 reviews)

Chic Village Cape w/sparkling pool! Walk to boutiques & eateries, bike to ocean!

East Hampton

27% off
S$6,197
for 7 nights, 1 home
S$885 per night
includes taxes & fees
Chic Village Cape w/sparkling pool! Walk to boutiques & eateries, bike to ocean!
Sunlit living room w/ coffered ceilings, tv, fireplace, & French doors to pool
Brightly lit dining room with 9' ceilings and view of heated swimming pool.
Second level sunny bedroom with queen bed and views of the pool.
Living room on main floor with mid-century modern sofa
Exceptional
(18 reviews)

Prime East Hampton Village Location. Heated Pool. Walk To All!

East Hampton

27% off
S$7,473
for 7 nights, 1 home
S$1,068 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
Living area
Dining
Private kitchen
Outdoor dining
Exceptional
(18 reviews)

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

Cutchogue

8% off
S$6,588
for 7 nights, 1 cottage
S$941 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Second living room
Wrap around deck
Second eating area
Living room
Exceptional
(34 reviews)

Our Peaceful, Beach Escape From the City

Sag Harbor

8% off
S$11,954
for 7 nights, 1 home
S$1,708 per night
includes taxes & fees
Our Peaceful, Beach Escape From the City
Dining
Living area
Living area
Interior
Exceptional
(9 reviews)

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

East Hampton

7% off
S$6,297
for 7 nights, 1 home
S$900 per night
includes taxes & fees
Modern Home in East Hampton great for a summer or winter retreat.
Dining
Terrace/patio
Interior
Private kitchen
Exceptional
(21 reviews)

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

Greenport

7% off
S$6,321
for 7 nights, 1 home
S$903 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
Living area
Interior
Exterior
Pool
Exceptional
(11 reviews)

Lovely Private Estate In East Hampton

East Hampton

7% off
S$6,638
for 7 nights, 1 home
S$948 per night
includes taxes & fees
Lovely Private Estate In East Hampton
Terrace/patio
Private kitchen
Room
Living area
Exceptional
(10 reviews)

Springs Chic, Steps from private Gardiners Bay beach!

East Hampton

7% off
S$7,699
for 7 nights, 1 home
S$1,100 per night
includes taxes & fees
Springs Chic, Steps from private Gardiners Bay beach!
Living area
Private kitchen
Dining
Interior
Exceptional
(13 reviews)

Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street

Sag Harbor

8% off
S$19,022
for 7 nights, 1 home
S$2,717 per night
includes taxes & fees
Enjoy a lovely summer retreat in Sag Harbor Village, 1 mile to Main Street
  • 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:

  • Mashomack Preserve (1.3 mi / 2.1 km)
  • 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)

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