Book the Best Places to Stay in Shelter Island Kayak

Find Curated Vacation Rentals, Boutique Cabins, and Stylish Eco-Friendly Acommodation in Shelter Island Kayak

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From US $845

         

10.0 (23 Reviews)

House

Waterfront House With Dock And Private Beach

• Air Conditioner
• Parking
• TV

• New York
• Shelter Island

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From US $208

         

|

10.0 (3 Reviews)

Apartment

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

• Parking
• View
• Balcony/Terrace

• New York
• Greenport

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From US $383

         

|

9.8 (26 Reviews)

Bed & Breakfast

Stirling House Bed & Breakfast

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From US $231

         

9.8 (120 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 $1,323

         

|

10.0 (1 Review)

House

Shelter Island Retreat w/Outdoor Pool!

• Parking
• Pool
• View

• New York
• Shelter Island Heights

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From US $737

         

9.4 (84 Reviews)

House

House on Chase Creek

• Air Conditioner
• Parking
• Balcony/Terrace

• Shelter Island Heights
• The Heights

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From US $346

         

9.8 (85 Reviews)

Cottage

Cottage on Beach front Estate Walk to Village

• Air Conditioner
• Parking
• Pet Friendly

• Greenport
• Pipes Cove

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From US $341

         

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9.9 (94 Reviews)

Bed & Breakfast

Seven Resort Style Inn near Beach

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Shelter Island Heights

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From US $867

         

10.0 (61 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 $1,566

         

10.0 (55 Reviews)

House

Work and Play Special! Extended Stay Discount

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Shelter Island

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From US $751

         

10.0 (55 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 $995

         

10.0 (30 Reviews)

House

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

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Shelter Island Heights

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From US $719

         

10.0 (28 Reviews)

House

Blue Bay Dream w/Seasonal Outdoor Jacuzzi, Cabana + Office

• Air Conditioner
• Parking
• Pet Friendly

• Greenport
• Pipes Cove

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From US $374

         

10.0 (28 Reviews)

Apartment

Charming Greenport Gem 1, 1 Mile to Ferry!

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From US $1,275

         

10.0 (22 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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From US $1,161

         

10.0 (19 Reviews)

House

Shelter Island Retreat With Pool, Home Theater, Close To Beach & Pet Friendly

• Air Conditioner
• Parking
• Pet Friendly

• Shelter Island Heights
• Silver Beach

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From US $2,228

         

10.0 (12 Reviews)

House

Stunning Waterfront Estate House with 270 degree sea views on 7 private acres

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Suffolk County

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From US $861

         

10.0 (12 Reviews)

House

Relaxation in Greenport

• Air Conditioner
• Parking
• TV

• Greenport
• Greenport West

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From US $1,377

         

10.0 (9 Reviews)

House

Cozy Greenport village cottage

• Air Conditioner
• Parking
• TV

• Greenport
• Pipes Cove

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From US $444

         

10.0 (8 Reviews)

House

Old meets new in this fully renovated 19th century farm house.

• Air Conditioner
• Parking
• TV

• Greenport
• Pipes Cove

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From US $1,967

         

10.0 (7 Reviews)

House

Huge Island Getaway Pool Hot Tub Walk To Beach

• Air Conditioner
• Parking
• Pet Friendly

• Shelter Island
• Menantic Creek

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From US $1,590

         

10.0 (6 Reviews)

House

Shelter Island Retreat w/Outdoor Pool!

• Air Conditioner
• Parking
• Pool

• New York
• Shelter Island Heights

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From US $603

         

10.0 (6 Reviews)

House

Northfork Townhouse walk to all

• Air Conditioner
• Parking
• Designated Smoking Area

• Greenport
• Greenport West

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From US $2,154

         

10.0 (4 Reviews)

Villa

New Construction Greenport Pool House - 3 Blocks from Town

• Air Conditioner
• Parking
• Pool

• New York
• Greenport

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★ Pro Tip: Bettertrips makes it easy to compare the best listings on Bettertrips homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Bettertrips 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 Kayak.