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Shelter Island Vacation Rentals

Find 753 available offers from 5 partners
Shelter Island
Anytime
Guests

Choose the perfect vacation rental

Price per night
Up to $100
$100 - $199
From $200
Accommodation types
House
Apartment
Bed and breakfast
Distance to center
1 km
2 km
5 km
Rating
4.5+
4+
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 753 properties

Best Vacation Home Deals on Shelter Island

Save up to 68%

House Shelter Island
Mar 30 - Apr 6
-57%
$351
$150 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Shelter Island with Yard & Grill
4.9
Outstanding (42 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Oct 14 - Oct 21
-20%
$618
$496 per night
House ∙ 30 guests ∙ 3 bedrooms
House in Northwest Harbor with Grill & Yard
Shelter Island, Suffolk County, New York, United States
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Cottage Shelter Island
Feb 3 - Feb 10
-68%
$540
$173 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Beautiful Cottage in North Fork with Grill & Yard + Pristine View
5.0
Outstanding (87 ratings)
Shelter Island, Suffolk County, New York, United States
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Discover a rental matching your expectations among the 753 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.

Top-Rated Rentals and Accommodations on Shelter Island

Book Vacation Rental Offers with the Highest User Rating

Cottage Shelter Island
Mar 30 - Apr 6
-67%
$585
$191 per night
Cottage ∙ 4 guests ∙ 2 bedrooms
Cottage in North Fork with Grill + Pristine View
5.0
Outstanding (79 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Oct 14 - Oct 21
-41%
$850
$500 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Shelter Island with Yard & Grill
5.0
Outstanding (29 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Dec 30 - Jan 6
-42%
$900
$522 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Shelter Island with Grill
5.0
Outstanding (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 $145 per night

House Shelter Island
Dec 30 - Jan 6
$463 per night
House ∙ 6 guests ∙ 3 bedrooms
Charming Vacation Home in Shelter Island Heights with Grill & Yard
5.0
Outstanding (9 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Oct 8 - Oct 15
-61%
$469
$185 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Sag Harbor with Free Parking
5.0
Outstanding (6 ratings)
Shelter Island, Suffolk County, New York, United States
Details
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House Shelter Island
Dec 30 - Jan 6
-42%
$900
$522 per night
House ∙ 8 guests ∙ 3 bedrooms
Wonderful House in Shelter Island with Pool, Yard & Grill
4.8
Outstanding (10 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Dec 26 - Jan 2
-20%
$379
$305 per night
House ∙ 8 guests ∙ 5 bedrooms
Charming Vacation Home in Shelter Island Heights with Usable Fireplace + Water Views
4.7
Excellent (7 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Dec 30 - Jan 6
-27%
$550
$400 per night
House ∙ 6 guests ∙ 3 bedrooms
Charming House in North Fork with Outdoor Fireplace
5.0
Outstanding (54 ratings)
Shelter Island, Suffolk County, New York, United States
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Apartment Shelter Island
Mar 23 - Mar 30
-38%
$335
$208 per night
Apartment ∙ 2 guests ∙ 1 bedroom
Apartment in Greenport
4.9
Outstanding (65 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Dec 30 - Jan 6
$343 per night
House ∙ 6 guests ∙ 3 bedrooms
Charming House in North Fork with Grill & Yard
4.9
Outstanding (38 ratings)
Shelter Island, Suffolk County, New York, United States
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Condo Shelter Island
Aug 4 - Aug 11
$442 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Condo in North Fork with Pool, Yard & Grill + Waterfront Views
4.9
Outstanding (79 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Mar 30 - Apr 6
-82%
$3,780
$675 per night
House ∙ 10 guests ∙ 4 bedrooms
Vacation Home in Sag Harbor with Wonderful Fireplace + Water Views
5.0
Outstanding (45 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
Dec 23 - Dec 30
$900 per night
House ∙ 9 guests ∙ 4 bedrooms
House in Shelter Island Heights with Pool, Yard & Grill + Porch Views
5.0
Outstanding (18 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Mar 9 - Mar 16
-59%
$1,150
$474 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Sag Harbor with Yard & Grill
4.8
Outstanding (44 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
Dec 9 - Dec 16
$399 per night
House ∙ 7 guests ∙ 3 bedrooms
House in North Fork with Indoor Fireplace
4.8
Outstanding (16 ratings)
Shelter Island, Suffolk County, New York, United States
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Vacation Rentals With Fireplaces

Get warm and cozy on cold winter nights on Shelter Island by booking a vacation home with a fireplace.

House  Shelter Island
Oct 9 - Oct 16
$540 per night
House ∙ 6 guests ∙ 3 bedrooms
Vacation Home in Shelter Island Heights with Yard & Grill
5.0
Outstanding (96 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
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Cottage  Shelter Island
Dec 16 - Dec 23
$315 per night
Cottage ∙ 3 guests ∙ 1 bedroom
Cottage in Sag Harbor with Abundant Parking + Panoramic View
4.9
Outstanding (86 ratings)
Shelter Island, Suffolk County, New York, United States
Fireplace
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House  Shelter Island
Dec 1 - Dec 8
-21%
$998
$785 per night
House ∙ 10 guests ∙ 5 bedrooms
Lovely Vacation Home in Shelter Island Heights with Outdoor Fireplace
5.0
Outstanding (1 rating)
Shelter Island, Suffolk County, New York, United States
Fireplace
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Shelter Island and book a vacation rental with air conditioning.

Cabin  Shelter Island
Dec 23 - Dec 30
$213 per night
Cabin ∙ 6 guests ∙ 2 bedrooms
Cabin in North Fork with Grill & Yard
5.0
Outstanding (5 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
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House  Shelter Island
Dec 1 - Dec 8
-47%
$943
$501 per night
House ∙ 10 guests ∙ 5 bedrooms
House in Noyack with Private Pool
4.9
Outstanding (52 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
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House  Shelter Island
Dec 1 - Dec 8
-78%
$2,000
$440 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Sagaponack with Grill, Pool & Yard
5.0
Outstanding (32 ratings)
Shelter Island, Suffolk County, New York, United States
Air conditioning
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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
Oct 8 - Oct 15
-66%
$421
$144 per night
House ∙ 8 guests ∙ 4 bedrooms
Pleasant House in Sag Harbor with Grill
4.5
Excellent
Shelter Island, Suffolk County, New York, United States
Balcony
Details
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House  Shelter Island
Dec 30 - Jan 6
-16%
$730
$610 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Shelter Island with 2-Car Garage
5.0
Outstanding (41 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
Details
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House  Shelter Island
Dec 22 - Dec 29
$290 per night
House ∙ 6 guests ∙ 3 bedrooms
House in Shelter Island with Grill, Pool & Yard
4.8
Outstanding (26 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony
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Popular Rental Amenities on Shelter Island

  • Pool (398)
  • Pet-friendly (140)
  • WiFi (731)
  • Air conditioning (705)
  • Kitchen (535)
  • TV (648)
  • Washing machine (419)
  • Microwave (464)
  • Parking (22)
  • Grill (434)
  • Dishwasher (437)
  • Fireplace (311)

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 50 of the listed rentals there provide "Crib."

Price and Availability Index in Shelter Island

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Vacation Rental Price Information on Shelter Island

The price graph will give you the nightly price average for the upcoming months of the year. Prices reach a peak a week in September. The price per night in a vacation rental on Shelter Island this week (9/14 - 9/21) costs on average $979. Prices drop in November to an average of $619 per night (11/11 - 11/18).

Rental availability information on Shelter Island

Check how busy Shelter Island is with our availability graph. So far, the week with the least available rentals on Shelter Island is in September (9/7 - 9/14). On the contrary, only 27% of the rentals are booked during a week in November (11/25 - 12/2).

The Weather on Shelter Island

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30°
9 days 9
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8 days 8
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45°
36°
7 days 7
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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
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63°
54°
5 days 5
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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

Wed, 27 Sep
62°
60°

0%

4 h

9 mi/h

Thu, 28 Sep
62°
60°

10%

7 h

9 mi/h

Fri, 29 Sep
64°
60°

15%

2 h

10 mi/h

Sat, 30 Sep
66°
60°

10%

6 h

14 mi/h

Sun, 1 Oct
71°
60°

0%

11 h

10 mi/h

Mon, 2 Oct
64°
59°

0%

11 h

7 mi/h

Tue, 3 Oct
64°
59°

10%

9 h

7 mi/h

Accommodations for your vacation on Shelter Island

In Shelter Island, many of the 753 accommodation types are house rental, which represent 66.22% of its available accommodations. Interestingly, the average rental fee for this type of accommodation in particular is $1,040 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 $711 per night for an area of 148 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 753 homes
💳 Possible discounts up to 73%
🌙 Nightly prices starting at $145
⭐ Popular amenities Pool, Pets allowed and Internet
🐾 Pet friendly homes 140 homes
🏊 Vacation rentals with pools 399 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 $145. If you’re interested in a house rental, the average price is $1,040 per night. A cabin Shelter Island will cost on average $711 per night.

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

Currently there are 753 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 399 vacation rentals available to book on Shelter Island.

Are pets allowed in vacation homes on Shelter Island?

Sure, currently there are 140 rentals on Shelter Island that allow dogs , with an average rate of $936 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.

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