Town of Southold Town Vacations & Trips from $797
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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.
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
$308 nightly
$352 total
Sep 9 - Sep 10
Total with taxes and fees
8.4/10 Very Good! (712 reviews)
"I booked thru Expedia but never checked in because you were SOLD OUzt! Expedia has a problem to fix!"
Reviewed on Sep 2, 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
$227 nightly
$256 total
Oct 1 - Oct 2
Total with taxes and fees
9.4/10 Exceptional! (333 reviews)
"Our room was clean and very spacious, the bathroom was large and modern. They setup a food shed outside with a nice menu and bar where you can sit down and have fresh oysters for example and a drink when returning from the wineries all day. The staff outside was super friendly. However, here are ..."
Reviewed on Sep 2, 2026
Zey Hotel
439 Main Street Greenport NY
$169 nightly
$193 total
Sep 20 - Sep 21
Total with taxes and fees
9.2/10 Wonderful! (393 reviews)
"Great location, and James is there for your every need! Not posh, but great value and a friendly staff make for a great experience in Greenport!"
Reviewed on Sep 2, 2026
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 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.
Photo by Joe Vickiana
Orient Beach State Park
8.6/10 (33 reviews)
You can take time to visit Orient Beach State Park during your travels to Orient. Stroll along the waterfront or discover the area's sunsets.
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.
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.
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.
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.
What to do in Town of Southold Town
Mystic Seaport Museum Adventure
$35
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.
