Stayifyoudare - Vacation Rentals in Truman's Beach

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From $300

         

New

Apartment

Quaint DT Greenport Apt - 2 Mi to Shelter Island!

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From $208

         

|

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 $383

         

|

9.8 (24 Reviews)

Bed & Breakfast

Stirling House Bed & Breakfast

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From $1,288

         

9.6 (5 Reviews)

House

Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now

• Air Conditioner
• Parking
• Pool

• New York
• Orient

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From $118

         

|

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 $469

         

|

9.2 (15 Reviews)

Bed & Breakfast

Arbor View House B&B

• Air Conditioner
• Parking
• Pool

• New York
• East Marion

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From $351

         

10.0 (81 Reviews)

Apartment

Bright Apartment - 1/2 Mi to Greenport Harbor!

• Air Conditioner
• TV
• View

• New York
• Greenport

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From $225

         

|

9.9 (24 Reviews)

Bed & Breakfast

The Stirling House Waterfront Inn Greenport

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From $334

         

|

9.2 (280 Reviews)

Hotel

Zey Hotel

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From $638

         

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 $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 $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 $540

         

10.0 (24 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 $284

         

10.0 (24 Reviews)

Apartment

Charming Greenport Gem 1, 1 Mile to Ferry!

• Air Conditioner
• Parking
• TV

• New York
• Greenport

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From $390

         

10.0 (23 Reviews)

Cottage

Orient Village — Historic Bayfront Cottage — 2025 Season

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From $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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From $609

         

10.0 (20 Reviews)

House

Walk to private bay beach, close to Greenport, wineries, golf! Premier Host home

• Air Conditioner
• Parking
• Pool

• New York
• East Marion

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From $1,755

         

10.0 (15 Reviews)

House

North Fork Entertainer's Delight!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From $812

         

10.0 (5 Reviews)

House

North Fork Paradise

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Town of Southold Town

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From $1,034

         

10.0 (4 Reviews)

House

SUMMER RETREAT: Beach, Dock & Pool overlooking the Peconic Bay in Greenport!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Greenport

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From $340

         

|

10.0 (3 Reviews)

House

Quiet 3BR home in East Marion. Private beach access 3 min walk away.

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Town of Southold Town

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From $449

         

10.0 (2 Reviews)

Hostel

American Beech - Luxury 2 Bedroom Apartment 10

• Air Conditioner
• TV
• View

• New York
• Greenport

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From $693

         

10.0 (1 Review)

Cottage

Charming 3-bedroom cottage in fabulous Greenport

• Air Conditioner
• Parking
• TV

• Greenport
• Greenport West

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From $555

         

10.0 (1 Review)

Cottage

The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town

• Air Conditioner
• Parking
• TV

• New York
• Town of Southold Town

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