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Shelter Island Vacation Rentals

Find 60 available offers from 5 partners
Shelter Island
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Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed & Breakfast
Distance to center
Max. 1 km
Max. 2 km
Max. 5 km
Rating
Outstanding: 4.5+
Very Good: 4+
Good: 3.5+

Experience heaven on earth with Shelter Island vacation rentals

Shelter Island is merely 90 miles west of Manhattan, but offers a tranquil escape from the humdrum of city life. Reach the 8,000-acre island sandwiched between North and South Forks of Long Island by ferry, to explore the 17 miles of unspoiled coastline.

Show all 60 properties
Save up to 57%

Best Vacation Home Deals on Shelter Island

House Shelter Island
Nov 3 - Nov 10
-45%
$1,194
$654 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in Shelter Island Heights with Gunite Pool
5.0
"Excellent" (6 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Mar 16 - Mar 23
-57%
$349
$150 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Shelter Island with Yard & Grill
5.0
"Excellent" (30 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Apr 22 - Apr 29
-40%
$1,200
$719 per night
House ∙ 10 guests ∙ 4 bedrooms
House in North Fork with Yard & Grill + Water Views
5.0
"Excellent" (127 ratings)
Shelter Island, Suffolk County, New York, United States
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Discover a rental matching your expectations among the 60 welcoming rentals from numerous vacation rental websites in Shelter Island. HomeToGo directly shows the best offers by comparing all of the listed properties in Shelter Island from its various partners.

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Top-Rated Rentals and Accommodations on Shelter Island

House Shelter Island
Apr 15 - Apr 22
-34%
$1,149
$764 per night
House ∙ 8 guests ∙ 4 bedrooms
Beautiful House in Shelter Island with Gunite Pool
5.0
"Excellent" (27 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Apr 7 - Apr 14
-42%
$533
$308 per night
House ∙ 4 guests ∙ 2 bedrooms
Nice Vacation Home in North Fork with Outside Patio
5.0
"Excellent" (25 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Aug 28 - Sep 4
$575 per night
House ∙ 7 guests ∙ 4 bedrooms
Family Friendly Vacation Home in Shelter Island Heights with Yard & Grill
4.8
"Excellent" (16 ratings)
Shelter Island, Suffolk County, New York, United States
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Recommended Vacation Rentals on Shelter Island

Find your perfect vacation rental on Shelter Island: from $150 per night

House Shelter Island
Apr 15 - Apr 22
-35%
$696
$529 per night
House ∙ 8 guests ∙ 3 bedrooms
Nice Vacation Home in North Fork with Grill & Yard
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Apr 15 - Apr 22
-55%
$500
$225 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Shelter Island Heights with Yard & Grill
4.6
"Outstanding" (15 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Mar 16 - Mar 23
-57%
$348
$149 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Shelter Island with Yard & Grill
5.0
"Excellent" (30 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Jan 19 - Jan 26
-45%
$611
$336 per night
House ∙ 6 guests ∙ 3 bedrooms
Bright House in North Fork with Yard & Grill
4.9
"Excellent" (48 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Oct 21 - Oct 28
-23%
$650
$497 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Shelter Island Heights with Grill, Yard & Pool
5.0
"Excellent" (8 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Apr 15 - Apr 22
$341 per night
House ∙ 6 guests ∙ 3 bedrooms
Charming House in North Fork with Grill & Yard
4.9
"Excellent" (36 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Jan 20 - Jan 27
$448 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Shelter Island Heights with Yard & Grill
4.9
"Excellent" (97 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Nov 3 - Nov 10
-45%
$1,151
$654 per night
House ∙ 9 guests ∙ 3 bedrooms
Vacation Home in Shelter Island Heights with Gunite Pool
5.0
"Excellent" (6 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Apr 15 - Apr 22
$392 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in North Fork with Yard & Grill
5.0
"Excellent" (2 ratings)
Shelter Island, Suffolk County, New York, United States
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Find Fantastic yet Inexpensive Offers

Budget-friendly Vacation Rentals on Shelter Island

Apartment Shelter Island
Mar 9 - Mar 16
-40%
$317
$190 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Greenport
4.9
"Excellent" (41 ratings)
Shelter Island, Suffolk County, New York, United States
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Apartment Shelter Island
Mar 16 - Mar 23
-16%
$263
$220 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Greenport
5.0
"Excellent" (52 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Oct 21 - Oct 28
-29%
$1,000
$712 per night
House ∙ 8 guests ∙ 4 bedrooms
Wonderful Vacation Home in North Fork with Wood-Burning Fireplace
4.9
"Excellent" (18 ratings)
Shelter Island, Suffolk County, New York, United States
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Vacation Houses With Pools

Make a splash on your next vacation! Over 51% of on Shelter Island vacation rentals have a swimming pool.

House Pool Shelter Island
Apr 8 - Apr 15
$650 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Shelter Island with 2-Car Garage
5.0
"Excellent" (42 ratings)
Shelter Island, Suffolk County, New York, United States
Pool
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House Pool Shelter Island
Apr 15 - Apr 22
-33%
$1,149
$768 per night
House ∙ 8 guests ∙ 4 bedrooms
Beautiful House in Shelter Island with Gunite Pool
5.0
"Excellent" (27 ratings)
Shelter Island, Suffolk County, New York, United States
Pool
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House Pool Shelter Island
Mar 16 - Mar 23
-29%
$1,000
$715 per night
House ∙ 8 guests ∙ 4 bedrooms
Wonderful Vacation Home in North Fork with Wood-Burning Fireplace
4.9
"Excellent" (18 ratings)
Shelter Island, Suffolk County, New York, United States
Pool
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Best vacation rentals with a balcony

Looking for a home with a balcony? Check out these vacation homes on Shelter Island with their own private patios and balconies.

House Balcony Shelter Island
Apr 7 - Apr 14
-40%
$1,200
$722 per night
House ∙ 10 guests ∙ 4 bedrooms
House in North Fork with Yard & Grill + Water Views
5.0
"Excellent" (128 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
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House Balcony Shelter Island
Jun 17 - Jun 24
$840 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Dering Harbor with Pool & Grill
4.9
"Excellent" (25 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
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Condo Balcony Shelter Island
Jan 19 - Jan 26
$441 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in North Fork with Pool, Yard & Grill + Waterfront Views
4.9
"Excellent" (67 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
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Apartments With Balconies or Patios

Looking for a home with a balcony? Check out these vacation homes on Shelter Island with their own private patios and balconies.

Apartment Balcony/Patio Shelter Island
Mar 9 - Mar 16
$221 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Rental Apartment in Greenport
5.0
"Excellent" (52 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
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House Balcony/Patio Shelter Island
Jun 17 - Jun 24
$575 per night
House ∙ 7 guests ∙ 4 bedrooms
Family Friendly Vacation Home in Shelter Island Heights with Yard & Grill
4.8
"Excellent" (16 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
Details
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Apartment Balcony/Patio Shelter Island
Mar 25 - Apr 1
-40%
$317
$190 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Greenport
4.9
"Excellent" (41 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
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Popular Rental Amenities on Shelter Island

  • Internet (789)
  • Air conditioning (761)
  • TV (712)
  • No smoking (682)
  • Kitchen (649)
  • Microwave (546)
  • Grill (519)
  • Dishwasher (516)
  • No pets (505)
  • Yard (499)
  • Washer (456)
  • Pool (417)

Our search page's filters will help you find the perfect rental in Shelter Island. You can easily search and find a rental matching your expectations in Shelter Island if you can't imagine a vacation without internet or you want to tune out with some TV time, as most accommodations provide "Internet" or "Air conditioning." You can also search for a property on Shelter Island if you want a rental with a sauna as 16 of the listed rentals there provide "Sauna."

The Weather on Shelter Island

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37°
30°
9 days 9
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39°
30°
8 days 8
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45°
36°
7 days 7
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55°
45°
7 days 7
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64°
54°
8 days 8
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73°
61°
6 days 6
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79°
68°
7 days 7
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77°
66°
5 days 5
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72°
61°
6 days 6
max.
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63°
54°
5 days 5
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50°
43°
5 days 5
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46°
37°
8 days 8
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Find the Shelter Island climate diagram. The highest average temperatures are in the month of July. No heat wave is expected in January, where minimum average temperatures usally hit a 30° low. The rainiest month is January while the driest month is August.

7-Day Weather Forecast on Shelter Island

Sun, 26 Mar
50°
44°

15%

10 h

17 mi/h

Mon, 27 Mar
48°
39°

15%

6 h

8 mi/h

Tue, 28 Mar
42°
39°

15%

0 h

7 mi/h

Wed, 29 Mar
46°
35°

0%

7 h

15 mi/h

Thu, 30 Mar
46°
42°

15%

1 h

19 mi/h

Fri, 31 Mar
44°
41°

15%

0 h

10 mi/h

Sat, 1 Apr
53°
44°

15%

3 h

24 mi/h

Accommodations for your vacation on Shelter Island

In Shelter Island, two-thirds of the 60 accommodation types are house rental, which represent 73.18% of its available accommodations. Interestingly, the average rental fee for this type of accommodation in particular is $1,329 a night, with an average size of 238 m². Furthermore, these accommodations are perfect for large groups, as most can accommodate 8 people. If you would prefer to book another accommodation type, you may want to check cabin, which are the second most typical type of accommodation in Shelter Island. Our data reveals that the average price of cabin is $759 per night for an area of 108 m².
What are the best activities for families on Shelter Island?

Spend time outdoors with kids

With 12 miles of coastline and 2,000 acres of woodlands, marshes, and creeks, Mashomack Preserve covers the entire south-eastern part of Shelter Island.

A nearby vacation cabin ensures quick access to the Field House to explore the interactive exhibit about the Preserve’s ecosystem. Choose from five hiking trails of varying lengths and spot ospreys, piping plovers, and least terns.

Where are the unique attractions on Shelter Island?

Relax and unwind by the sea

Rent a beach house on the secluded and tranquil Shell Beach. This narrow beach extends into the Shelter Island Sound. Bask in the sun, watch plovers hop close to the waters edge, and be mesmerized by the colorful wildflowers in the vicinity, and the panoramic views of the South Fork and West Neck Harbor.

Information about vacation rentals on Shelter Island

🏡 Vacation rentals 60 properties
💳 Possible discounts up to 47%
🌙 Nightly prices starting at $149
⭐ Popular amenities Internet, Air conditioning and TV
🐾 Pet friendly accommodations 197 properties
🏊 Vacation rentals with pools 435 properties

Frequently Asked Questions

What is the average price per night for a vacation home on Shelter Island?

The nightly price of accommodations on Shelter Island starts at $149. If you’re interested in a house rental, the average price is $1,329 per night. A cabin Shelter Island will cost $759 per night on average.

How many vacation rentals are available to book on Shelter Island?

There are 60 rentals on Shelter Island to browse and rent for your upcoming trip.

What are the most popular amenities for vacation homes on Shelter Island?

Three most popular amenities for vacation home rentals on Shelter Island include accommodations that have: Air conditioning, Internet, and TV.

How many vacation homes with a pool are on Shelter Island?

There are 435 vacation rentals from 5 providers on Shelter Island.

Are dogs allowed in vacation rentals on Shelter Island?

Sure, there are 197 vacation rentals on Shelter Island that allow dogs and the average price is $1,281 per night.

What's the best month to travel to Shelter Island?

If you are booking a vacation rental on Shelter Island, keep in mind that rainy season is usually in January or February, with August often being the driest.

We list offers from thousands of providers, including:

Booking.com Vacation Rentals on Shelter Island TripAdvisor Vacation Rentals on Shelter Island Vrbo Vacation Rentals on Shelter Island VacationRentals.com Vacation Rentals on Shelter Island HouseTrip Vacation Rentals on Shelter Island FlipKey Vacation Rentals on Shelter Island Homestay.com Vacation Rentals on Shelter Island Only-apartments Vacation Rentals on Shelter Island Interhome Vacation Rentals on Shelter Island Novasol Vacation Rentals on Shelter Island HomeEscape Vacation Rentals on Shelter Island

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