Truman's Beach Tours

Whether it's a romantic honeymoon or a family vacation, a trip to the seaside is sure to keep you happy. Enjoy a leisurely stroll together along the water's edge at Trumans Beach.

If you love hearing the word "free" as much as most travelers, you'll be glad to know this stretch of coastline is just that! Trumans Beach is located in Town of Southold Town. If you want to keep your travel schedule full while you're around these parts, also stop by Orient Beach State Park, Kontokosta Winery and 67 Steps Beach.

Plan a trip to see Truman's Beach

Price found within the past 48 hours. Click for updated prices.
Stonybrook Motel & Lodge

Stonybrook Motel & Lodge

2 out of 5
Save 100% on your flight
Price was $887, price is now $469 per person
$469
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Burlington (BTV)
7.6/10 Good! (1,000 reviews)
Perfectly fine for a quick stay and great price. WiFi didn’t work in room, otherwise, clean, hot shower, comfortable bed and pillows. Dining options within 15 minutes

Reviewed on Nov 11, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was $2,035, price is now $1,166 per person
$1,166
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (NYC)
8.8/10 Excellent! (1,000 reviews)
The view is soooo good!

Reviewed on Dec 2, 2025

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
Price was $1,446, price is now $847 per person
$847
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
The price was most we ever paid for a room($907 night) We were there for the NYC Marathon and wanted to be in that area. We had a $25 day credit towards food and drinks, one morning we ate in restaurant and breakfast for 2 people was $104 before tip. They charge me $10 cup for coffee when it was complimentary in the lobby. We returned after long day and they did not leave washcloths, I went to front desk, she called housekeeping and said they would have them right up, 30 minutes later I called and they said they were on there way, after waiting I finally returned to front desk and told lady to tell me where to go and I would go get me some washcloths, she went herself and got some, when I returned to room my wife said housekeeping came but said they could only find one washcloth and brought it. $907 night, do your homework before you go.

Reviewed on Nov 10, 2025

Popular places to visit

Island's End Golf & Country Club

Enjoy a round of golf in Orient at Island's End Golf & Country Club. While you're in the area, stroll along the beautiful beaches.

Island's End Golf & Country Club

Oysterponds Historical Society

You can spend time browsing the exhibits at Oysterponds Historical Society during your travels in Orient. While you're in the area, stroll along the beautiful beaches.

Oysterponds Historical Society

Island's End Golf and Country Club

4/5(2 reviews)

Enjoy a round of golf in East Marion at Island's End Golf and Country Club. Wander the beautiful beaches in this family-friendly area.

Island's End Golf and Country Club

Norman E. Klipp Marine Park

If a restful vacation is part of your travel plans, Norman E. Klipp Marine Park might be the perfect place to seek out during your trip to Greenport. While you're in the area, wander around the parks.

Norman E. Klipp Marine Park

Safe Harbor Stirling

Explore the waterfront in Greenport with a trip to Safe Harbor Stirling. While you're in the area, stroll along the beaches.

Safe Harbor Stirling

Kontokosta Winery

4/5(9 reviews)

You can enjoy a tasting or tour at Kontokosta Winery during your travels to Greenport West. Wander the beautiful beaches in this family-friendly area.

Kontokosta Winery

Best Lodging Options Near Truman's Beach

Arbor View House B&B

Arbor View House B&B

3.5 out of 5
8900 Main Road East Marion NY
Arbor View House B&B
The Blue Inn At North Fork

The Blue Inn At North Fork

2.5 out of 5
7850 Main Rd East Marion NY
The Blue Inn At North Fork
The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
209 Front St Greenport NY
The Harbor Front Inn
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

Orient NY
Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home
Zey Hotel

Zey Hotel

3.5 out of 5
439 Main Street Greenport NY
Zey Hotel
American Beech Hotel

American Beech Hotel

3.5 out of 5
300 Main Street Greenport NY
American Beech Hotel
Shelter Island Spacious Getaway with Cozy Fireplace

Shelter Island Spacious Getaway with Cozy Fireplace

Shelter Island Heights NY
Shelter Island Spacious Getaway with Cozy Fireplace
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
Sound View Greenport
The Menhaden

The Menhaden

3.5 out of 5
207 Front St Greenport NY
The Menhaden
See all 1,949 properties in Truman's Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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