Holiday In The Hamptons - Vacation Rentals in Truman's Beach

Quaint DT Greenport Apt - 2 Mi to Shelter Island! From US $208
         

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10.0 (3 Reviews)
Apartment
  • Parking
  • View
  • Balcony/Terrace
Stirling House Bed & Breakfast From US $383
         

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9.8 (25 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
House by the Bay with Large In-ground Pool, Steps from Beach From US $852
         

10.0 (27 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bright Apartment - 1/2 Mi to Greenport Harbor! From US $236
         

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9.9 (13 Reviews)
Apartment
  • Parking
  • View
  • Ocean View
Arbor View House B&B From US $469
         

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9.2 (15 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool
Brand new 2 bedroom, Greenport Village, walk to town Marina Views! From US $708
         

The Stirling House Waterfront Inn Greenport From US $225
         

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9.8 (20 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Zey Hotel From US $308
         

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9.2 (342 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
North Fork Paradise From US $1,097
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
American Beech - Luxury 2 Bedroom Apartment 10 From US $1,072
         

Charming 3-bedroom cottage in fabulous Greenport From US $859
         

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home From US $2,240
         

9.4 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Bright and Spacious Summer Home Steps from the Beach From US $690
         

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

Truman's Beach Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Truman's Beach?
How many vacation rentals are available in Truman's Beach?

Currently, the total number of properties listed in 2026 is over 218 in the Truman's Beach area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Truman's Beach.