Town of Southold Town Vacations & Trips from $800
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Top destinations in Town of Southold Town
Orient
Greenport
Southold
Mattituck
Cutchogue
East Marion
Peconic
Fishers Island
The Latest Town of Southold Town Vacation Packages
Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge
$1,893
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (1,012 reviews)
Didn’t allow me to get late checkout . Upon arrival the valet wasn’t even outside to help with baggage , for such an expensive hotel , I’d say my expectations were completely unmet
Reviewed on Aug 16, 2026
Find the Best Town of Southold Town Vacation Packages
Town of Southold Town Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | MacArthur Airport (ISP) |
Town of Southold Town Hotel Deals
Sound View Greenport
58775 County Rd 48 Greenport NY
$334 nightly
$381 total
Sep 9 - Sep 10
Total with taxes and fees
8.4/10 Very Good! (690 reviews)
"The hotel itself and experience was very lovely. There were a few little noticeable things along the way for instance, the bed, pillow, and towels all had small stains. The mirrors in the bathroom were dirty and smudges. The water pressure in the shower was really, really strong where it hurt your ..."
Reviewed on Aug 16, 2026
North Fork Resort
690 Queen St Greenport NY
$275 nightly
$314 total
Sep 13 - Sep 14
Total with taxes and fees
Zey Hotel
439 Main Street Greenport NY
$243 nightly
$278 total
Aug 31 - Sep 1
Total with taxes and fees
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.
Stay near popular Town of Southold Town attractions
Orient Point County Park
10.0/10 (1 review)
Explore the great outdoors at Orient Point County Park, a lovely green space in Orient Point. Stroll along the beaches or discover the area's sunsets.
Photo by 4 Star Traveler
Pindar Vineyards
8.4/10 (8 reviews)
You can enjoy a tasting or tour at Pindar Vineyards during your travels to Peconic. Discover the area's sunsets and wineries.
Photo by Adriana T
Bedell Cellars
8.6/10 (4 reviews)
You can enjoy a tasting or tour at Bedell Cellars during your travels to Cutchogue. While you're in the area, stroll along the beautiful beaches.
Macari Vineyards
8.0/10 (1 review)
You can enjoy a tasting or tour at Macari Vineyards during your travels to Mattituck. While you're in the area, stroll along the beautiful beaches.
Peconic Bay Winery
You can enjoy a tasting or tour at Peconic Bay Winery during your travels to Cutchogue. While you're in the area, stroll along the beautiful beaches.
67 Steps Beach
9.6/10 (26 reviews)
Why not spend a carefree afternoon at 67 Steps Beach during your travels in Greenport? Take in the festivals and sunsets in the area.
Raphael Winery
You can enjoy a tasting or tour at Raphael Winery during your travels to Peconic. Wander the beaches or discover the area's sunsets.
Kontokosta Winery
9.2/10 (48 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.
What to do in Town of Southold Town
Mystic Seaport Museum Adventure
$40
per adult
92% of travellers recommend
Mystic: Guided Ghost Tour of Downtown Mystic at Night
$35
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
