Vacation Rentals in Shelter Island, NY
PRICE PER NIGHT
ACCOMMODATION TYPES
Private Hamptons Cottage with excellent WiFi!
9.8
Excellent
·
Shelter Island
·
5 br
·
Fitness Center · Workspace · Outdoor Space ·
From
$900/nightProperty
House · 5 Beds · 3 baths
Amenities
Fitness Center
Private Pool
Beach
Pool
Dishwasher
Oven
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Perfect Family Summer Vacation Home Close to beach 18x42 pool
9.7
Excellent
·
Shelter Island
·
3 br
·
Sleeps 6
·
Private Pool · Beach · Pool ·
From
$557/nightProperty
House · 3 Beds · 3 baths
Amenities
Private Pool
Beach
Pool
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Kitchen
The Pridwin Hotel
8.7
Very good
·
Shelter Island
·
1 br
·
Sleeps 4
·
Assigned Parking · Free Parking · On Site Laundry ·
From
$245/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Free Parking
On Site Laundry
Beach
Pool
Wifi
Air Conditioning
Furnished
Other spaces
Workspace
Rams Head Inn
9
Excellent
·
Shelter Island
·
1 br
·
Sleeps 4
·
Assigned Parking · Free Parking · Outdoor Space ·
From
$619/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Free Parking
Beach
Fireplace
Air Conditioning
Furnished
Package Service
Residents Lounge
Shelter Island Retreat with Outdoor Pool!
No reviews
·
Shelter Island
·
5 br
·
Sleeps 10
·
Balcony · Beach · Pool ·
From
$951/nightProperty
Apartment · 5 Beds · 7 baths
Amenities
Beach
Pool
Fireplace
Oven
In Unit Laundry
Wifi
Furnished
Swimming Pool
Other spaces
Balcony, Kitchen
The House by Wades
10
Excellent
·
Shelter Island
·
3 br
·
Sleeps 6
·
In Unit Laundry · Wifi · Kitchen ·
From
$500/nightProperty
House · 3 Beds · 2 baths
Amenities
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Shelter Island Retreat With Pool ...A Stone's Throw Away From The Beach!
10
Excellent
·
Shelter Island
·
3 br
·
Sleeps 9
·
On Site Laundry · Fitness Center · Workspace ·
From
$800/nightProperty
House · 3 Beds · 3 baths
Amenities
On Site Laundry
Fitness Center
Private Pool
Beach
Pool
Fireplace
Dishwasher
Oven
Other spaces
Workspace, Kitchen
Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
10
Excellent
·
Shelter Island
·
4 br
·
Sleeps 8
·
Central Heat · Deck · Fitness Center ·
From
$876/nightProperty
House · 4 Beds · 3 baths
Amenities
Central Heat
Fitness Center
Private Pool
Beach
Pool
Fireplace
Dishwasher
Oven
Other spaces
Deck, Workspace, Kitchen
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Lovely home by the sea with dock and heated Gunite pool!
10
Excellent
·
Shelter Island
·
4 br
·
Sleeps 10
·
Waterfront · Fitness Center · Balcony ·
From
$519/nightProperty
House · 4 Beds · 3 baths
Amenities
Waterfront
Fitness Center
Private Pool
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
Bright, open waterfront house with gorgeous sunsets and private beach
No reviews
·
Shelter Island
·
5 br
·
Sleeps 10
·
Waterfront · Workspace · Outdoor Space ·
From
$571/nightProperty
House · 5 Beds · 3 baths
Amenities
Waterfront
Beach
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Updated Greek Revival home minutes to beaches and amenities
No reviews
·
Shelter Island
·
5 br
·
Sleeps 7
·
Pool · In Unit Laundry · Wifi ·
From
$395/nightProperty
House · 5 Beds · 3 baths
Amenities
Pool
In Unit Laundry
Wifi
Air Conditioning
Furnished
Swimming Pool
Other spaces
Kitchen
Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve
9.6
Excellent
·
Shelter Island
·
3 br
·
Sleeps 6
·
Deck · Balcony · Private Pool ·
From
$300/nightProperty
House · 3 Beds · 2 baths
Amenities
Private Pool
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Deck, Balcony, Kitchen
Shelter Island 4 bedroom waterfront home with home office
No reviews
·
Shelter Island
·
4 br
·
Sleeps 10
·
On Site Laundry · Waterfront · Workspace ·
From
$1,153/nightProperty
House · 4 Beds · 3 baths
Amenities
On Site Laundry
Waterfront
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Sleek Shelter Island With Pool, Preserve And Water Rights:
9.3
Excellent
·
Shelter Island
·
3 br
·
Sleeps 8
·
Private Pool · Pool · Dishwasher ·
From
$1,022/nightProperty
House · 3 Beds · 5 baths
Amenities
Private Pool
Pool
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Beautiful, Spacious Home with Pool, Water Access & Fenced Acre on Private Road.
10
Excellent
·
Shelter Island
·
5 br
·
Sleeps 10
·
Hardwood Floor · Waterfront · Fitness Center ·
From
$1,413/nightProperty
House · 5 Beds · 4 baths
Amenities
Hardwood Floor
Waterfront
Fitness Center
Private Pool
Beach
Pool
Fireplace
Dishwasher
Other spaces
Workspace, Kitchen
Stunning, modern with heated Gunite pool near Wades Beach
10
Excellent
·
Shelter Island
·
4 br
·
Sleeps 8
·
Balcony · Private Pool · Pool ·
From
$770/nightProperty
House · 4 Beds · 4 baths
Amenities
Private Pool
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Balcony, Kitchen
Elegant Retreat -- 14 night minimum. No exceptions.
8.8
Very good
·
Shelter Island
·
4 br
·
Sleeps 8
·
High Ceilings · Fitness Center · Workspace ·
From
$402/nightProperty
House · 4 Beds · 3 baths
Amenities
High Ceilings
Fitness Center
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Charming Shelter Island Oasis
10
Excellent
·
Shelter Island
·
4 br
·
Sleeps 5
·
Balcony · Private Pool · Pool ·
From
$919/nightProperty
House · 4 Beds · 4 baths
Amenities
Private Pool
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Air Conditioning
Furnished
Other spaces
Balcony, Kitchen
Waterfront Treehouse with Pool
No reviews
·
Shelter Island
·
4 br
·
Sleeps 7
·
Workspace · Private Pool · Pool ·
From
$786/nightProperty
House · 4 Beds · 3 baths
Amenities
Private Pool
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Peaceful get away with Tranquil Salt Water Pool
10
Excellent
·
Shelter Island
·
4 br
·
Sleeps 6
·
Private Pool · Beach · Pool ·
From
$956/nightProperty
House · 4 Beds · 3 baths
Amenities
Private Pool
Beach
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Other spaces
Kitchen
Shelter Island Hidden Waterfront Gem
10
Excellent
·
Shelter Island
·
3 br
·
Sleeps 8
·
Lake · Hot Tub · Waterfront ·
From
$1,069/nightProperty
House · 3 Beds · 3 baths
Amenities
Lake
Hot Tub
Waterfront
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Waterfront House With Dock And Private Beach
10
Excellent
·
Shelter Island
·
3 br
·
Sleeps 6
·
Central Heat · Waterfront · Balcony ·
From
$850/nightProperty
House · 3 Beds · 3 baths
Amenities
Central Heat
Waterfront
Beach
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Chic and renovated beach house in a Shelter Island waterfront community,...
No reviews
·
Shelter Island
·
4 br
·
Sleeps 6
·
Hardwood Floor · Balcony · Outdoor Space ·
From
$461/nightProperty
House · 4 Beds · 3 baths
Amenities
Hardwood Floor
Private Pool
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Stylish, Country 4 BR Retreat August Preferable
No reviews
·
Shelter Island
·
4 br
·
Sleeps 9
·
Workspace · In Unit Laundry · Wifi ·
From
$600/nightProperty
House · 4 Beds · 4 baths
Amenities
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Shelter Island - Newly Renovated Home with Heated Outdoor Pool
9.6
Excellent
·
Shelter Island
·
4 br
·
Sleeps 8
·
Deck · Balcony · Workspace ·
From
$1,250/nightProperty
House · 4 Beds · 3 baths
Amenities
Private Pool
Beach
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Other spaces
Deck, Balcony, Workspace, Kitchen
Modern and Efficient Beachfront Paradise
No reviews
·
Shelter Island
·
3 br
·
Sleeps 6
·
Coffee Tea Maker · Waterfront · Fitness Center ·
From
$2,000/nightProperty
House · 3 Beds · 4 baths
Amenities
Coffee Tea Maker
Waterfront
Fitness Center
Beach
Fireplace
Dishwasher
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
Gorgeous, Tranquil 9000 Sq Ft Home On Dering Harbor
10
Excellent
·
Shelter Island
·
6 br
·
Sleeps 12
·
Waterfront · Private Pool · Beach ·
From
$2,700/nightProperty
House · 6 Beds · 10 baths
Amenities
Waterfront
Private Pool
Beach
Pool
Dishwasher
Oven
In Unit Laundry
Wifi
Other spaces
Kitchen
Paradise found on Shelter Island
10
Excellent
·
Shelter Island
·
5 br
·
Sleeps 10
·
Fitness Center · Workspace · Beach ·
From
$886/nightProperty
House · 5 Beds · 5 baths
Amenities
Fitness Center
Beach
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Charming A-frame Home On Private Quiet Road
9.9
Excellent
·
Shelter Island
·
3 br
·
Sleeps 4
·
Hardwood Floor · Dishwasher · Oven ·
From
$325/nightProperty
House · 3 Beds · 1 bath
Amenities
Hardwood Floor
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Charming, Renovated Island Cottage - Shelter Island License #: 012-2017
9.8
Excellent
·
Shelter Island
·
2 br
·
Sleeps 4
·
Ceiling Fan · Fitness Center · Dishwasher ·
From
$260/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
Ceiling Fan
Fitness Center
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Charming, Historic Cottage
No reviews
·
Shelter Island
·
3 br
·
Sleeps 6
·
Fitness Center · Beach · Fireplace ·
From
$650/nightProperty
Apartment · 3 Beds · 2 baths
Amenities
Fitness Center
Beach
Fireplace
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Private wooded summer house 5 minute walk to Wades Beach
10
Excellent
·
Shelter Island
·
3 br
·
Sleeps 6
·
Outdoor Space · Beach · Fireplace ·
From
$775/nightProperty
House · 3 Beds · 2 baths
Amenities
Beach
Fireplace
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Kitchen
Congdon's Point Shelter Island
No reviews
·
Shelter Island
·
5 br
·
Sleeps 11
·
High Ceilings · Hot Tub · Hardwood Floor ·
From
$2,500/nightProperty
House · 5 Beds · 6 baths
Amenities
High Ceilings
Hot Tub
Hardwood Floor
Pool
Fireplace
Dishwasher
Oven
In Unit Laundry
Other spaces
Balcony, Kitchen
MID-ISLAND RETREAT. Newly renovated, 5 bedrooms, sleeps 8.
10
Excellent
·
Shelter Island
·
5 br
·
Sleeps 8
·
Lake · Waterfront · Workspace ·
From
$550/nightProperty
House · 5 Beds · 2 baths
Amenities
Lake
Waterfront
Beach
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Other spaces
Workspace, Kitchen
Gorgeous 2 bedroom garage apartment with parking for two cars
No reviews
·
Shelter Island
·
2 br
·
Sleeps 4
·
Dishwasher · In Unit Laundry · Wifi ·
From
$757/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Dishwasher
In Unit Laundry
Wifi
Air Conditioning
Furnished
Residents Lounge
Other spaces
Kitchen
WATERFRONT with Private Beach Boat Dock and Launch Ramp
No reviews
·
Shelter Island
·
2 br
·
Sleeps 6
·
Balcony · Workspace · Outdoor Space ·
From
$852/nightProperty
House · 2 Beds · 3 baths
Amenities
Dishwasher
Oven
In Unit Laundry
Wifi
Air Conditioning
Furnished
Other spaces
Balcony, Workspace, Kitchen
Relax in this Spacious, Light-Filled Vacation Home with Pool in Silver Beach
No reviews
·
Shelter Island
·
3 br
·
Sleeps 6
·
Ceiling Fan · Hardwood Floor · Fitness Center ·
From
$600/nightProperty
House · 3 Beds · 3 baths
Amenities
Ceiling Fan
Hardwood Floor
Fitness Center
Private Pool
Beach
Pool
Fireplace
Dishwasher
Other spaces
Balcony, Kitchen
Showing 1 - 37 of 37 results
Updated: March 31, 2023
Learn about vacation rentals in
Shelter Island
Explore 37 vacation rentals near Shelter Island, New York. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Shelter Island, you can see photos of Shelter Island vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Shelter Island vacation rentals in specific areas. Whether you’re looking for a Shelter Island staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Shelter Island is $245 per night and the highest price is $2,700 per night.
32 of the vacation rentals near Shelter Island are houses.
The average bathroom count for a vacation house near Shelter Island is
4. The average price for vacation houses near Shelter Island is $913 per night. There are 21 vacation homes under this price. The most common
amenities for vacation rentals near Shelter Island are: furnished, air conditioning, and wifi. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
2 available
2 bed rentals
3 available
3 bed rentals
12 available
4+ bed rentals
20 available
Getting around Shelter Island
Walking
2/10
You’ll need another mode of transportation for getting around. Scooter, anyone?
Driving
9/10
Commuting is easy with multiple accessible routes and plenty of parking.
Transit
0/10
FYI, there are little to no public transit options within walking distance.
Points of interest in Shelter Island
Groceries
2/10
No grocery stores within walking distance
Shopping
2/10
Few or no shops within walking distance
Cafes
0/10
Few or no cafés within walking distance
Restaurants
2/10
Few or no restaurants within walking distance
Nightlife
2/10
Few or no bars within walking distance
Which price range for vacation rentals is considered a good deal in Shelter Island, NY area?
Vacation Rental Price Information in Shelter Island, NY
The graph shows the percentages of vacation homes in each price bucket. Shelter Island, NY has the largest percentage (59.28%) of homes in $500+ price range.
$0 - $50
1
units
$50 - $100
2
units
$100 - $150
8
units
$150 - $200
13
units
$200 - $250
9
units
$250 - $300
9
units
$300 - $350
9
units
$350 - $400
8
units
$400 - $450
9
units
$500+
99
units
Vacation Rentals in Shelter Island, NY FAQ
How many vacation rentals in Shelter Island are available?
There are currently 37 vacation rentals in Shelter Island available. Our vacation rentals in Shelter Island include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Shelter Island?
Yes, right now there are 15 pet friendly vacation rentals in Shelter Island. A pet friendly vacation rental in Shelter Island means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Shelter Island with a pool?
Yes there are vacation rentals with a pool available in Shelter Island, NY. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Shelter Island with internet access?
As of March 31, 2023, there are vacation rentals with internet access available in Shelter Island, New York. Check out more enjoyable destinations on Vacations by Zumper.
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