Town of Southold Town Vacations & Trips from $1,223
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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.
Hotel Riu Plaza New York Times Square
Manhattan
$1,362
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,313 reviews)
The hotel was great! We are a family of 5 and in NYC most places wanted us to book 2 rooms. I found RIU and the price was awesome. When we arrived the staff was professional and all of them were genuinely thankful we chose to stay there. The hotel was very clean. There was a woman cleaning the lobby every time we stepped foot in it. The hotel looked super fancy as my tween girls said! Our room was great and we would stay here again! Thank you RIU staff and Expedia.
Reviewed on Aug 28, 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
$350 nightly
$400 total
Sep 21 - Sep 22
Total with taxes and fees
North Fork Resort
690 Queen St Greenport NY
$286 nightly
$326 total
Sep 27 - Sep 28
Total with taxes and fees
The Shoals Suites and Slips
61600 Main Rd Southold NY
$345 nightly
$391 total
Sep 13 - Sep 14
Total with taxes and fees
9.4/10 Exceptional! (329 reviews)
"This place has a later check in than most hotels of 4.00pm . But even then the room wasn’t available until 4.40pm. The room is very cool with a non functional small tv, but nice patio area outside the room. The lobby/breakfast area did not open at the advertised time and the offerings were pathetic. ..."
Reviewed on Aug 27, 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 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 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.
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.
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.
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
$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.
