Shelter Island Vacation Rentals - HomeToGo base64Hash Shelter Island Vacation Rentals - HomeToGo

Shelter Island Vacation Rentals

Find 607 available offers from 9 partners
Shelter Island
Anytime
Guests
Shelter Island
Anytime
Guests

Popular Filters to find the Perfect Home Rental on Shelter Island

2 Adults
1 Bedroom
Pool
House
Pets allowed
4 Adults
Cabin

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 743 properties

Vacation Houses With Pools

Make a splash on your next vacation! Over 52% of on Shelter Island vacation rentals have a swimming pool.

House  Shelter Island
May 15 - May 22
$405 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Shelter Island Heights with Patio, Yard & Pool

4.9
Outstanding (49 ratings)
Shelter Island, Suffolk County, New York, United States
Pool
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House  Shelter Island
Jun 8 - Jun 15
$1,000 per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation Home in North Fork with Grill, Patio & Yard

5.0
Outstanding (32 ratings)
Shelter Island, Suffolk County, New York, United States
Pool
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House  Shelter Island
May 20 - May 27
$760 per night
House ∙ 10 guests ∙ 5 bedrooms

Wonderful House in Shelter Island with Grill, Pool & Patio

5.0
Outstanding (55 ratings)
Shelter Island, Suffolk County, New York, United States
Pool
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Dog-Friendly Vacation Rentals

Bring Fido on your next trip and book a stay in one of these pet-friendly rentals on Shelter Island!

Cottage  Shelter Island
Nov 3 - Nov 10
$185 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Beautiful Cottage in North Fork with Patio, Grill & Yard + Pristine View

5.0
Outstanding (98 ratings)
Shelter Island, Suffolk County, New York, United States
Pet-friendly
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Cottage  Shelter Island
Nov 3 - Nov 10
$203 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage in North Fork with Patio & Grill + Pristine View

5.0
Outstanding (79 ratings)
Shelter Island, Suffolk County, New York, United States
Pet-friendly
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House  Shelter Island
Jun 8 - Jun 15
$870 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Dering Harbor with Pool, Grill & Patio

5.0
Outstanding (31 ratings)
Shelter Island, Suffolk County, New York, United States
Pet-friendly
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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  Shelter Island
Nov 3 - Nov 10
$675 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Shelter Island with 2-Car Garage

5.0
Outstanding (42 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
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House  Shelter Island
Aug 10 - Aug 17
$733 per night
House ∙ 6 guests ∙ 3 bedrooms

House in Shelter Island with Grill, Pool & Patio

4.9
Outstanding (27 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
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House  Shelter Island
Jul 8 - Jul 15
$225 per night
House ∙ 4 guests ∙ 1 bedroom

Vacation Home in North Fork with Patio & Yard

5.0
Outstanding (5 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
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Best Vacation Home Deals on Shelter Island

Save up to 70%

House Shelter Island
Nov 3 - Nov 10
-70%
$571
$171 per night
House ∙ 6 guests ∙ 2 bedrooms

House in North Fork with Patio, Grill & Yard

5.0
Outstanding (5 ratings)
Shelter Island, Suffolk County, New York, United States
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Apartment Shelter Island
Nov 3 - Nov 10
-34%
$325
$215 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Lovely Apartment in North Fork with Yard

5.0
Outstanding (15 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Nov 3 - Nov 10
-70%
$571
$171 per night
House ∙ 6 guests ∙ 2 bedrooms

Vacation Home in North Fork

5.0
Outstanding (6 ratings)
Shelter Island, Suffolk County, New York, United States
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Discover a rental matching your expectations among the 607 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.

Recommended Vacation Rentals on Shelter Island

Find your perfect vacation rental on Shelter Island: from $228 per night

House Shelter Island
May 20 - May 27
$1,000 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful House in North Haven with Patio, Yard & Grill + Open Views

5.0
Outstanding (8 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
May 20 - May 27
$1,120 per night
House ∙ 14 guests ∙ 5 bedrooms

House in Sag Harbor with Pool, Patio & Yard

4.9
Outstanding (94 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
May 20 - May 27
$1,029 per night
House ∙ 12 guests ∙ 6 bedrooms

House in Sag Harbor with Grill & Patio

5.0
Outstanding (21 ratings)
Shelter Island, Suffolk County, New York, United States
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Apartment Shelter Island
Nov 3 - Nov 10
-33%
$349
$236 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in Greenport with Patio

5.0
Outstanding (82 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Nov 3 - Nov 10
$440 per night
House ∙ 6 guests ∙ 3 bedrooms

Charming Vacation Home in Shelter Island Heights with Patio, Grill & Yard

5.0
Outstanding (12 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Aug 17 - Aug 24
$943 per night
House ∙ 30 guests ∙ 3 bedrooms

House in Northwest Harbor with Grill, Yard & Patio

Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Nov 3 - Nov 10
$715 per night
House ∙ 8 guests ∙ 4 bedrooms

Wonderful Vacation Home in North Fork with Wood-Burning Fireplace

5.0
Outstanding (24 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Nov 3 - Nov 10
$750 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Shelter Island Heights with Yard, Patio & Grill

4.7
Excellent (20 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Nov 3 - Nov 10
$799 per night
House ∙ 8 guests ∙ 4 bedrooms

House in Shelter Island with Grill, Yard & Patio + Water Views

5.0
Outstanding (35 ratings)
Shelter Island, Suffolk County, New York, United States
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Budget-friendly Vacation Rentals on Shelter Island

Find Fantastic yet Inexpensive Offers

House Shelter Island
Jul 8 - Jul 15
$850 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in Shelter Island with Patio, Yard & Grill

5.0
Outstanding (29 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Nov 3 - Nov 10
$500 per night
House ∙ 6 guests ∙ 3 bedrooms

Vacation Home in North Fork with Yard, Grill & Patio

5.0
Outstanding (100 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Jun 14 - Jun 21
$1,073 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Sag Harbor with In-Ground Pool

5.0
Outstanding (69 ratings)
Shelter Island, Suffolk County, New York, United States
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Top-Rated Rentals and Accommodations on Shelter Island

Book Vacation Rental Offers with the Highest User Rating

House Shelter Island
Nov 3 - Nov 10
-30%
$357
$250 per night
House ∙ 4 guests ∙ 2 bedrooms

House in North Fork with Private Parking + Water Views

5.0
Outstanding (51 ratings)
Shelter Island, Suffolk County, New York, United States
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Apartment Shelter Island
May 2 - May 9
$375 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in North Fork with Patio, Yard & Grill

4.9
Outstanding (84 ratings)
Shelter Island, Suffolk County, New York, United States
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Apartment Shelter Island
May 17 - May 24
-31%
$294
$202 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Apartment in Greenport with Patio

4.9
Outstanding (66 ratings)
Shelter Island, Suffolk County, New York, United States
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Popular Rental Amenities on Shelter Island

  • Pool (388)
  • Pet-friendly (144)
  • WiFi (731)
  • Air conditioning (713)
  • Kitchen (519)
  • TV (658)
  • Washing machine (406)
  • Microwave (441)
  • Parking (22)
  • Grill (401)
  • Dishwasher (412)
  • Fireplace (337)

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 want a rental with a pool or you are looking for a pet-friendly rental, as most accommodations provide "Pool" or "Pets allowed." You can also search for a property on Shelter Island if you need a crib for your baby as 106 of the listed rentals there provide "Crib."

The Weather on Shelter Island

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9 days 9
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39°
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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°
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63°
54°
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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

Tue, 23 Apr
55°
50°

5%

5 h

6 mi/h

Wed, 24 Apr
60°
53°

10%

4 h

9 mi/h

Thu, 25 Apr
50°
46°

0%

6 h

9 mi/h

Fri, 26 Apr
53°
50°

15%

6 h

7 mi/h

Sat, 27 Apr
53°
51°

0%

3 h

10 mi/h

Sun, 28 Apr
53°
53°

15%

0 h

13 mi/h

Mon, 29 Apr
55°
55°

10%

3 h

7 mi/h

Accommodations for your vacation on Shelter Island

In Shelter Island, many of the 743 accommodation types are house rental, which represent 64.34% of its available accommodations. Interestingly, the average rental fee for this type of accommodation in particular is $1,097 a night, with an average size of 225 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 $717 per night for an area of 153 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 available 743 rentals
💳 Possible discounts up to 23%
🌙 Nightly prices starting at $228
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 141 homes
🏊 Vacation rentals with pools 386 homes

Frequently Asked Questions

What is the average nightly price for a vacation rental on Shelter Island?

The nightly price of accommodations on Shelter Island starts at $228. If you’re interested in a house rental, the average price is $1,097 per night. A cabin Shelter Island will cost on average $717 per night.

How many vacation rentals are available for booking on Shelter Island?

Currently there are 743 vacation rentals on Shelter Island to choose from and rent for your upcoming trip.

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

The most popular amenities for vacation home rentals on Shelter Island include accommodations that have: Pool, Pets allowed, and Internet.

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

Choose from 386 vacation rentals available to book on Shelter Island.

Are pets allowed in vacation homes on Shelter Island?

Sure, currently there are 141 rentals on Shelter Island that allow dogs , with an average rate of $967 per night.

What's the best time of year to travel to Shelter Island?

If choosing a vacation home on Shelter Island, consider that rainy season is typically in January or February, with August often being the driest.

Find the perfect Shelter Island home to match your style

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