Southold Vacations
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Find the Best Southold Vacation Packages
Southold Hotel Deals
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is NT$5,415 per night from May 3 to May 4
NT$5,415
NT$6,987 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (253 reviews)
Simply delightful!
Reviewed on 2026/3/30
Vine & Sand
47100 New York 25 Southold NY
The price is NT$12,425 per night from Apr 7 to Apr 8
NT$12,425
NT$14,196 total
Apr 7 - Apr 8
includes taxes & fees
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!
Reviewed on 2026/3/22
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is NT$8,026 per night from Apr 21 to Apr 22
NT$8,026
NT$9,781 total
Apr 21 - Apr 22
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Enjoyable stay.
Reviewed on 2026/3/28
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.
Discover the most popular places to visit in Southold
Sparkling Pointe
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
Osprey's Dominion
You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
Croteaux Vineyards
You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.
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- Sag Harbor Whaling and Historical Museum
- Shinnecock Hills Golf Course
- The Style Bar
- Agawam Park
- Railroad Museum of Long Island
- Visit Hamptons
- Sparkling Pointe
- Scarola Vineyards
- Orient Beach State Park
- Shinn Estate Vineyards
- Visit Cutchogue
- Harbes Family Farm
- Shelter Island Historical Society
- Greenport Farmers' Market
- Ocean Road Beach
- Cedar Point County Park
- Jamesport Vacations
- Elizabeth A. Morton National Wildlife Refuge
- Visit Noyack
- Off the Rocker
- Orient Vacations
- Truman's Beach
- Visit Peconic
- Corey Creek Winery
- Sunset Beach
- Clovis Point
- Hallockville Museum Farm
- Croteaux Vineyards
- Southampton Cultural Center
- Greenport Carousel
- Palmer Vineyards
- Duck Walk Vineyards
- 67 Steps Beach
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- Car rental Greenport
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- Enterprise Rental Cars in Greenport
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
