Rent The Cottages - Vacation Rentals in Shelter Island Country Club

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From US $297

         

9.8 (67 Reviews)

Apartment

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From US $208

         

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10.0 (2 Reviews)

Apartment

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

• Parking
• View
• Accessibility

• New York
• Greenport

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From US $383

         

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9.8 (24 Reviews)

Bed & Breakfast

Stirling House Bed & Breakfast

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From US $740

         

10.0 (22 Reviews)

House

Waterfront House With Dock And Private Beach

• Air Conditioner
• Parking
• TV

• New York
• Shelter Island

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From US $118

         

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10.0 (2 Reviews)

Apartment

Charming Greenport Gem 1, 1 Mile to Ferry!

• Parking
• Accessibility
• Security/Safety

• New York
• Greenport

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From US $211

         

9.4 (79 Reviews)

House

House on Chase Creek

• Air Conditioner
• Parking
• Balcony/Terrace

• Shelter Island Heights
• The Heights

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From US $480

         

9.8 (102 Reviews)

Cottage

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

• Air Conditioner
• Parking
• Pet Friendly

• Greenport
• Pipes Cove

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From US $914

         

10.0 (1 Review)

House

Beachfront Greenport Villa

• Air Conditioner
• Parking
• Security/Safety

• New York
• Greenport

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From US $330

         

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9.2 (12 Reviews)

Bed & Breakfast

Harbor Knoll Bed & Breakfast

• Parking
• Pool
• Private Pool

• Greenport
• Pipes Cove

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From US $266

         

10.0 (73 Reviews)

Cottage

Cottage on Beach front Estate with Dockage .Walk to Village

• Air Conditioner
• Parking
• Pet Friendly

• Greenport
• Pipes Cove

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From US $563

         

10.0 (150 Reviews)

Apartment

Private & Spacious Five Room Suite.Steps To Bay Beach and walk to Village.

• Air Conditioner
• Parking
• TV

• Greenport
• Pipes Cove

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From US $351

         

10.0 (83 Reviews)

Apartment

Bright Apartment - 1/2 Mi to Greenport Harbor!

• Air Conditioner
• TV
• View

• New York
• Greenport

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From US $485

         

10.0 (82 Reviews)

Condo

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

• Air Conditioner
• Parking
• Pool

• Greenport
• Greenport West

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From US $758

         

10.0 (55 Reviews)

House

1820 Whaling Captain's Home - A walk to a coffee or cocktail!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Greenport

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From US $1,123

         

10.0 (53 Reviews)

House

Work and Play Special! Extended Stay Discount

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Shelter Island

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From US $605

         

10.0 (53 Reviews)

House

Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From US $939

         

10.0 (30 Reviews)

House

Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Shelter Island

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From US $593

         

10.0 (27 Reviews)

House

House by the Bay with Large In-ground Pool, Steps from Beach

• Air Conditioner
• Parking
• Pet Friendly

• New York
• East Marion

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From US $284

         

10.0 (27 Reviews)

Apartment

Charming Greenport Gem 1, 1 Mile to Ferry!

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From US $695

         

10.0 (26 Reviews)

House

Brand new 2 bedroom, Greenport Village, walk to town Marina Views!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Greenport

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From US $540

         

10.0 (26 Reviews)

House

Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Greenport

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From US $487

         

10.0 (25 Reviews)

House

Cleves Point Estates Home, Private sandy beach

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Greenport

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From US $160

         

10.0 (23 Reviews)

House

Aqua Vista

• Air Conditioner
• Parking
• Pet Friendly

• Greenport
• Pipes Cove

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From US $1,285

         

10.0 (20 Reviews)

House

Gorgeous 5 bdrm home with beautiful bay views in the heart of Greenport Village

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Greenport

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★ Pro Tip: Rentthecottages makes it easy to compare the best listings on Rentthecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Rentthecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Shelter Island Country Club.