Shelter Island holiday rentals

We found 2,294 holiday rentals — enter your dates for availability
Discover a selection of 92 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:13 Nov - 20 Nov

Dining
Living area
Pool
Living area
Exceptional
(10 reviews)

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

Orient

8% off
S$16,016
for 7 nights, 1 room
S$2,288 per night
includes taxes & fees
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
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$74,372
for 7 nights, 1 home
S$10,625 per night
includes taxes & fees
Everything in Hamptons special discount available for weekly and monthly renters
The Harbor
Private kitchen
Exterior
Dining Room
Exceptional
(97 reviews)

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

Sag Harbor

16% off
S$10,980
for 7 nights, 1 home
S$1,569 per night
includes taxes & fees
Beautiful 3600sq ft Sag Harbor Village Home, Saltwater Pool, Walk to Beach &Town
Pool
Exterior
Spacious Main Floor Living room
Exterior
Exceptional
(11 reviews)

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

Southold

7% off
S$12,871
for 7 nights, 1 home
S$1,839 per night
includes taxes & fees
New Modern Farmhouse Estate Living in the heart of Southold with a pool!!!
Exterior
Terrace/patio
Pool
Living area
Exceptional
(8 reviews)

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

Water Mill

8% off
S$50,137
for 7 nights, 1 home
S$7,162 per night
includes taxes & fees
Stunning fall sunsets, coveted location on Mecox Bay - recently furnished
Private kitchen
Pool area viewed from side with teak loungers and umbrellas
Main house living room
Covered porch on backside of main house
Exceptional
(6 reviews)

Amagansett Beach Estate with Award Winning Outdoor Amenities

Amagansett

8% off
S$43,848
for 7 nights, 1 home
S$6,264 per night
includes taxes & fees
Amagansett Beach Estate with Award Winning Outdoor Amenities
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
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
S$21,234
for 7 nights, 1 home
S$3,033 per night
includes taxes & fees
Completely Renovated Home on ~2 Private Acres, Near Beach/Town
Terrace/patio
Pool
Living area
Private kitchen
Exceptional
(17 reviews)

PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH

East Hampton

8% off
S$21,202
for 7 nights, 1 home
S$3,029 per night
includes taxes & fees
PRIVATE POOL ~ PERFECT HAMPTONS GETAWAY ~ WBH
Front Porch
Pool
New Kitchen
Living room w/ screen porch beyond
Exceptional
(46 reviews)

Quiet Family Friendly Hideaway With Pool And Poolhouse

East Hampton

8% off
S$17,087
for 7 nights, 1 home
S$2,441 per night
includes taxes & fees
Quiet Family Friendly Hideaway With Pool And Poolhouse
Hall into sitting room
Master bed onto balcony
Dining room from kitchen
Dining room onto porch
Exceptional
(34 reviews)

Bohemian Old Life Saving Station with Beach & Pool

East Marion

8% off
S$13,108
for 7 nights, 1 home
S$1,873 per night
includes taxes & fees
Bohemian Old Life Saving Station with Beach & Pool
Living area
Dining
Private kitchen
Room
Exceptional
(18 reviews)

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

Cutchogue

8% off
S$6,354
for 7 nights, 1 cottage
S$908 per night
includes taxes & fees
Great Getaway! Exceptional Home. Walking distance to The Christmas Tree Shoppe
Pool
Outdoor dining
Private kitchen
Living area
Exceptional
(13 reviews)

Explore the Hampton in this Shelter Island Getaway. Weekly Bookings

Shelter Island Heights

31% off
S$7,433
for 7 nights, 1 home
S$1,062 per night
includes taxes & fees
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
Pool
Living area
Interior
Exceptional
(10 reviews)

Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL

Sag Harbor

8% off
S$19,148
for 7 nights, 1 cottage
S$2,735 per night
includes taxes & fees
Just Posted for Summer 2026! SECLUDED SAG HARBOR COTTAGE w/ HUGE POOL
Interior
Terrace/patio
Living area
Pool
Exceptional
(11 reviews)

Large East Hampton house with heated pool and home gym - fully fenced

East Hampton

12% off
S$16,840
for 7 nights, 1 home
S$2,406 per night
includes taxes & fees
Large East Hampton house with heated pool and home gym - fully fenced
Main living room and dining room
Dining
Interior
Interior
Exceptional
(28 reviews)

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

Sag Harbor

8% off
S$19,070
for 7 nights, 1 home
S$2,724 per night
includes taxes & fees
9BR Sag Harbor PRIVATE w/ Pool-Tennis- B-ball- HotTub
Room
Private kitchen
Property grounds
Private kitchen
Exceptional
(14 reviews)

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

Southold

8% off
S$5,876
for 7 nights, 1 home
S$839 per night
includes taxes & fees
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
Living area
Private kitchen
Living area
Exterior
Exceptional
(34 reviews)

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

Cutchogue

8% off
S$3,463
for 7 nights, 1 cottage
S$495 per night
includes taxes & fees
Totally Renovated Cottage on the North Fork 7 min. walk to the Beach
Bar area pass-through to kitchen, with bar seating.
Living room, looking out toward Accabonac Harbor, water views.
Kitchen with Wolf stove, Sub Zero fridge, pass-through serving area to dining.
Guest house small private
outdoor seating area.
Exceptional
(7 reviews)

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

East Hampton

8% off
S$20,591
for 7 nights, 1 home
S$2,942 per night
includes taxes & fees
WATER VIEWS RETREAT, SPRINGS, EAST HAMPTON, POOL, FIRE PIT, 10 MINUTES TO BEACH!
kitchen leading into open plan living area
huge swimming pool and deck surrounded by trees
kitchen backs onto the garden
Queen bedroom leading onto deck.  Ensuite bathroom, walk-in closet and tv.
Exceptional
(53 reviews)

Large heated pool, games room, private bay beach access, gardens, kid-friendly

East Hampton

8% off
S$6,545
for 7 nights, 1 home
S$935 per night
includes taxes & fees
Large heated pool, games room, private bay beach access, gardens, kid-friendly
Main living area
Large pool heated pool
Kitchen
Exterior
Exceptional
(20 reviews)

Charming, spacious 3 bedroom, 3 bath East Hampton Springs house

East Hampton

7% off
S$6,625
for 7 nights, 1 home
S$946 per night
includes taxes & fees
Charming, spacious 3 bedroom, 3 bath East Hampton Springs house
Private kitchen
Dining
Living area
Pool
Exceptional
(9 reviews)

Chic Modern Private Designer 1.5 Acre Private Oasis

East Hampton

26% off
S$38,340
for 7 nights, 1 home
S$5,477 per night
includes taxes & fees
Chic Modern Private Designer 1.5 Acre Private Oasis
From the bedroom
Facade
Front yard closeup
Zepherine Drouhin, c. 1868 French thornless rose cultivar famed for its scent
Exceptional
(22 reviews)

Private Hamptons cottage in ideal Amagansett location

Amagansett

8% off
S$6,903
for 7 nights, 1 cottage
S$986 per night
includes taxes & fees
Private Hamptons cottage in ideal Amagansett location
Three Mile Harbor, glorious sunsets, and waterfront restaurants- 8 minute drive
Brightly lit dining room with 9' ceilings and view of heated swimming pool.
Sunlit living room w/ coffered ceilings, tv, fireplace, & French doors to pool
Second level sunny bedroom with queen bed and views of the pool.
Exceptional
(18 reviews)

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

East Hampton

15% off
S$9,692
for 7 nights, 1 home
S$1,385 per night
includes taxes & fees
Prime East Hampton Village Location. Heated Pool. Walk To All!
Private kitchen
Terrace/patio
Interior
Dining
Exceptional
(19 reviews)

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

Greenport

8% off
S$6,076
for 7 nights, 1 home
S$868 per night
includes taxes & fees
Entire, new, roomy, village beach house close to beach, park, and town center
  • 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)
  • Elizabeth A. Morton National Wildlife Refuge (5.8 mi / 9.3 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