210+ Vacation Rentals Near Truman's Beach |
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  2. New York
  3. Truman's Beach

Trips to Truman's Beach

Plan Your Next Trip to Truman's Beach and explore unforgettable sights, local flavors, and exciting experiences.

Property Image From $301
         

New
Apartment
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
  • Air Conditioner
  • Parking
  • TV

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Property Image From $208
         

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10.0 (2 Reviews)
Apartment
Quaint DT Greenport Apt - 2 Mi to Shelter Island!
  • Parking
  • View
  • Accessibility

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Property Image From $346
         

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10.0 (62 Reviews)
Apartment
55 m² Apartment ∙ 1 bedroom ∙ 2 guests
  • 592 ft² Apartment
  • Air Conditioner
  • View
  • Ocean View

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Property Image From $383
         

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9.8 (23 Reviews)
Bed & Breakfast
Stirling House Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV

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Property Image From $1,305
         

9.6 (5 Reviews)
House
Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $118
         

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10.0 (2 Reviews)
Apartment
Charming Greenport Gem 1, 1 Mile to Ferry!
  • Parking
  • Accessibility
  • Security/Safety

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Property Image From $271
         

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10.0 (40 Reviews)
Apartment
37 m² Apartment ∙ 1 bedroom ∙ 2 guests
  • 398 ft² Apartment
  • Air Conditioner
  • Parking
  • TV

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Property Image From $469
         

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9.2 (15 Reviews)
Bed & Breakfast
Arbor View House B&B
  • Air Conditioner
  • Parking
  • Pool

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Property Image From $351
         

10.0 (80 Reviews)
Apartment
Bright Apartment - 1/2 Mi to Greenport Harbor!
  • Air Conditioner
  • TV
  • View

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Property Image From $225
         

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9.9 (24 Reviews)
Bed & Breakfast
The Stirling House Waterfront Inn Greenport
  • Air Conditioner
  • Parking
  • TV

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Property Image From $246
         

10.0 (9 Reviews)
Apartment
83 m² Apartment ∙ 2 bedrooms ∙ 6 guests
  • 893 ft² Apartment
  • Air Conditioner
  • Parking
  • TV

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Property Image From $301
         

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9.2 (275 Reviews)
Hotel
Zey Hotel
  • Air Conditioner
  • Parking
  • TV

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Property Image From $646
         

10.0 (27 Reviews)
House
House by the Bay with Large In-ground Pool, Steps from Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $236
         

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9.8 (14 Reviews)
Apartment
Bright Apartment - half Mi to Greenport Harbor!
  • Parking
  • View
  • Ocean View

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Property Image From $695
         

10.0 (26 Reviews)
House
Brand new 2 bedroom, Greenport Village, walk to town Marina Views!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $268
         

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9.2 (14 Reviews)
Bed & Breakfast
Arbor View House Bed and Breakfast
  • Air Conditioner
  • Parking
  • View

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Property Image From $487
         

10.0 (25 Reviews)
House
Cleves Point Estates Home, Private sandy beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $550
         

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New
House
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $540
         

10.0 (24 Reviews)
House
Beautifully renovated 2 Bedroom, 1st Floor apt -Greenport Village, Walk to town!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $306
         

New
Villa
BayFront Cottage
  • Air Conditioner
  • Parking
  • View

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Property Image From $384
         

10.0 (23 Reviews)
Cottage
Orient Village — Historic Bayfront Cottage — 2025 Season
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $400
         

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8.8 (218 Reviews)
Bed & Breakfast
ZEY HOTEL
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $291
         

10.0 (23 Reviews)
Apartment
Charming Greenport Gem 1, 1 Mile to Ferry!
  • Air Conditioner
  • Parking
  • TV

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Property Image 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

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

Weather in Truman's Beach

View the weather forecast for Truman's Beach before booking your Truman's Beach Vacation Rentals to confirm your best time to go.

December - February
High 42°F       Low 18°F
March - May
High 65°F       Low 22°F
June - August
High 79°F       Low 56°F
September - November
High 76°F       Low 29°F

Top Attractions Around Truman's Beach, NY

Smartours offers a large selection of top attractions around Truman's Beach. Research things to do on your vacation before you visit Truman's Beach.


The Hamptons Beaches Orient Beach State Park Bay Street Theatre Kontokosta Winery Rocky Neck State Park Sparkling Pointe Bedell Cellars Pindar Vineyards Tanger Outlets Harvey's Beach Raphael Winery 67 Steps Beach Corey Creek Winery Mashomack Preserve Pollock-Krasner House and Study Center Florence Griswold Museum Orient Point County Park Beach Bungalow The Old Field Vineyards Orient By The Sea Marina