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Shelter Island Vacation Rentals

Find 606 available offers from 9 partners
Shelter Island
Anytime
Guests
Shelter Island
Anytime
Guests

Popular Filters to find the Perfect Rental in Shelter Island

2 Adults
1 Bedroom
4 Adults
Pets allowed
Pool
House
Internet

Dog-Friendly Vacation Rentals

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

House  Shelter Island
$256 per night
House ∙ 4 guests ∙ 2 bedrooms

House in North Fork with Wood-Burning Fireplace + Jaw-Dropping Views

4.8
Outstanding (13 ratings)
Shelter Island, Suffolk County, New York, United States
Pet-friendly
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House  Shelter Island
$796 per night
House ∙ 8 guests ∙ 4 bedrooms

Vacation Home in Sagaponack with Grill, Pool & Patio

5.0
Outstanding (42 ratings)
Shelter Island, Suffolk County, New York, United States
Pet-friendly
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Cottage  Shelter Island
$141 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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Apartments with a balcony or patio

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

House  Shelter Island
$1,111 per night
House ∙ 12 guests ∙ 3 bedrooms

Pleasant House in Sag Harbor with Wood-Burning Fireplace + Private Views

5.0
Outstanding (14 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
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House  Shelter Island
$626 per night
House ∙ 7 guests ∙ 3 bedrooms

House in North Fork with Grill, Yard & Patio

5.0
Outstanding (2 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
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House  Shelter Island
$453 per night
House ∙ 8 guests ∙ 4 bedrooms

Beautiful House in Springs with Grill, Patio & Yard

5.0
Outstanding (2 ratings)
Shelter Island, Suffolk County, New York, United States
Balcony/Patio
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Vacation homes and cottages with a garden

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Shelter Island with private yards.

House  Shelter Island
$510 per night
House ∙ 8 guests ∙ 4 bedrooms

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

4.9
Outstanding (31 ratings)
Shelter Island, Suffolk County, New York, United States
Yard
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House  Shelter Island
$858 per night
House ∙ 12 guests ∙ 6 bedrooms

Vacation Home in North Sea with Sauna, Yard & Patio

5.0
Outstanding (8 ratings)
Shelter Island, Suffolk County, New York, United States
Yard
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House  Shelter Island
$1,197 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
Yard
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Best Vacation Home Deals in Shelter Island

Save up to 8%

House Shelter Island
May 10 - May 17
-8%
$776
$714 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
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Find the ideal vacation home from $141 per night by searching through the 606 properties available in Shelter Island. HomeToGo instantly highlights the best offers by comparing all of the available vacation rentals in Shelter Island from 9 different providers.

Recommended Vacation Rentals in Shelter Island

Find your perfect vacation rental in Shelter Island: from $117 per night

House Shelter Island
$807 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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Aparthotel Shelter Island
Aug 8 - Aug 15
$1,041 per night
Aparthotel ∙ 6 guests ∙ 1 bedroom

Beautiful Aparthotel in Greenport West with Patio, Grill & Pool

4.4
Very good (176 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
$1,088 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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Cottage Shelter Island
$174 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
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House Shelter Island
$869 per night
House ∙ 8 guests ∙ 4 bedrooms

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

5.0
Outstanding (14 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
$1,298 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
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House Shelter Island
$1,293 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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House Shelter Island
$186 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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Apartment Shelter Island
$209 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Rental Apartment in North Fork

4.8
Outstanding (8 ratings)
Shelter Island, Suffolk County, New York, United States
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Budget-friendly Rentals in Shelter Island

Find Fantastic yet Inexpensive Rentals

Cottage Shelter Island
May 10 - May 17
$953 per night
Cottage ∙ 8 guests ∙ 1 bedroom

Cottage in Springs with Grill & Pool

Shelter Island, Suffolk County, New York, United States
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Apartment Shelter Island
$362 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
$664 per night
House ∙ 10 guests ∙ 4 bedrooms

Vacation Home in Sag Harbor with Wood-Burning Fireplace

5.0
Outstanding (6 ratings)
Shelter Island, Suffolk County, New York, United States
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Top-Rated Offers and Accommodations in Shelter Island

Book Vacation Rentals with the Highest User Rating

House Shelter Island
$1,074 per night
House ∙ 10 guests ∙ 5 bedrooms

House in Shelter Island Heights with Large Patio + Water Views

4.9
Outstanding (16 ratings)
Shelter Island, Suffolk County, New York, United States
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House Shelter Island
$1,447 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
$180 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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Popular Rental Amenities in Shelter Island

  • Pool (387)
  • WiFi (727)
  • Kitchen (515)
  • Pet-friendly (142)
  • Air conditioning (709)
  • TV (654)
  • Washing machine (402)
  • Parking (22)
  • Microwave (437)
  • Dishwasher (411)
  • Balcony/patio (528)
  • Grill (399)

You will have a large selection of vacation rentals to choose from if you are looking for an accommodation offering a pool in Shelter Island. In addition, more hotel room offer a pool than aparthotel. Most of the hotel room with pools in Shelter Island accommodate 5 vacationers and have an average cost of $1,175 a night. If you would also like to be close to the water, two-thirds of the vacation rentals offering a pool are located within 2 kilometres of the waterfront.

The Weather in Shelter Island

max.
Min.

-1°
9 days 9
max.
Min.

-1°
8 days 8
max.
Min.

7 days 7
max.
Min.
13°
7 days 7
max.
Min.
18°
12°
8 days 8
max.
Min.
23°
16°
6 days 6
max.
Min.
26°
20°
7 days 7
max.
Min.
25°
19°
5 days 5
max.
Min.
22°
16°
6 days 6
max.
Min.
17°
12°
5 days 5
max.
Min.
10°
5 days 5
max.
Min.

8 days 8
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

Above are the weather conditions for Shelter Island. In July maximum temperatures go higher than 26°. On the contrary, the coolest month is January. According to the climate diagram, January is the rainiest month of the year in Shelter Island.

7-Day Weather Forecast in Shelter Island

Tue., 23 Apr.
13°
10°

5%

5 h

10 km/h

Wed., 24 Apr.
16°
12°

10%

4 h

14 km/h

Thu., 25 Apr.
10°

0%

6 h

15 km/h

Fri., 26 Apr.
12°
10°

15%

6 h

12 km/h

Sat., 27 Apr.
12°
11°

0%

3 h

17 km/h

Sun., 28 Apr.
12°
12°

15%

0 h

21 km/h

Mon., 29 Apr.
13°
13°

10%

3 h

11 km/h

Information about vacation rentals in Shelter Island

🏡 Vacation rentals available 606 rentals
🌙 Nightly prices starting at $141
⭐ Popular amenities Pool, Internet and Kitchen
🐾 Pet friendly homes 142 homes
🏊 Vacation rentals with pools 299 homes

Frequently Asked Questions

What is the typical availability of vacation rentals in Shelter Island?

At the moment, there are 743 vacation homes from 9 different providers in Shelter Island.

What are the most popular vacation home amenities in Shelter Island?

When looking to book a vacation home in Shelter Island, the most requested amenities include Pool, Internet, and Kitchen.

Are there pet-friendly vacation rentals in Shelter Island?

Finding a vacation rental in Shelter Island that allows dogs is definitely possible, with 140 pet-friendly homes on offfer.

What's the best month to visit Shelter Island?

If you're looking for balmy weather, July and August are typically the hottest months in Shelter Island with temperatures around 26 °C. January and February in Shelter Island are the coldest, with -1 °C on average.

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