Town of Southold Town Vacations & Trips from $634
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Top destinations in Town of Southold Town
Greenport
Southold
Mattituck
Cutchogue
Orient Point
Greenport West
Orient
East Marion
Fishers Island
The Latest Town of Southold Town Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Radio Hotel
Oct 7 - Oct 11Radio Hotel + Flight
Manhattan4 nights4.0 star property8.6/10 - Excellent (2,492 reviews)Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop EWR - ATL • Nonstop - The Wall Street Hotel
Oct 22 - Oct 25The Wall Street Hotel + Flight
Manhattan3 nights5.0 star property9.6/10 - Exceptional (733 reviews)"Excellent Staff, clean rooms, etc.. in room dining. However roof terrace is only for exclusive events"Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - LGA • Nonstop EWR - ATL • Nonstop - Hotel Riu Plaza Manhattan Times Square
Oct 7 - Oct 11Hotel Riu Plaza Manhattan Times Square + Flight
Manhattan4 nights4.0 star property9.2/10 - Wonderful (3,834 reviews)"Awesome overnight trip for dinner and a show. Location was excellent."Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop EWR - ATL • Nonstop - Hotel Riu Plaza New York Times Square
Oct 7 - Oct 11Hotel Riu Plaza New York Times Square + Flight
Manhattan4 nights4.0 star property9.0/10 - Wonderful (3,268 reviews)"I am extremely disappointed with my stay at Riu Plaza New York Times Square. We stayed in Room 2516, and on the morning of our checkout we realized we had accidentally left behind an Alo shopping bag that we had purchased the night before. We immediately notified the front desk after checking out. We are 100% certain the bag was left in the room because the only place we went after shopping was straight back to the hotel. The hotel later told us that “the housekeeper didn’t find anything.”..."Reviewed August 2, 2026Roundtrip • Atlanta (ATL) - New York (JFK)ATL - EWR • Nonstop EWR - ATL • Nonstop - Pestana Park Avenue
Oct 17 - Oct 22Pestana Park Avenue + Flight
Manhattan5 nights4.0 star property9.2/10 - Wonderful (890 reviews)"Clean room and very pleasant"Reviewed August 2, 2026Roundtrip • Dallas (DFW) - New York (JFK)DFW - LGA • Nonstop LGA - DFW • Nonstop
Discover the most popular places to visit in Town of Southold Town
What to do in Town of Southold Town
Mystic: Guided Ghost Tour of Downtown Mystic at Night
$35
per adult
94% of travelers recommend
Sunday Brunch Sail in Greenport
$149
per adult
0% of travelers recommend
Town of Southold Town Hotel Deals
The Shoals Suites and Slips
The Shoals Suites and Slips3.5 star property
1.5 mi from Town of Southold Town
9.4 out of 10, Exceptional, (310 reviews)
9.4/10
Exceptional
(310 reviews)
"We stayed at the Shoals for 3 nights. Something I didn't realize was that there are no rooms directly facing the water - all rooms look out to the parking lot. The property and rooms were very clean and very well maintained, however many things were lacking.
1.) MAJOR concern: We asked for a pack n play for our baby and they brought up a mattress with it. We looked up the mattress brand (Spring Spirit) and it was recalled in 2024!! Parents: please check all the items you receive!! We were...
$345 nightly
The price is $391
$391 total
Sep 1 - Sep 2
Total with taxes and fees
9.2 out of 10, Wonderful, (366 reviews)
9.2/10
Wonderful
(366 reviews)
"Water issues in the room. Hot water only from sink faucet and shower water turned off sudsed-up mid-shower. They turned it on when my husband went down to complain. Convenient location but has its quirks."
$243 nightly
The price is $278
$278 total
Aug 18 - Aug 19
Total with taxes and fees
8.4 out of 10, Very Good, (674 reviews)
8.4/10
Very Good
(674 reviews)
$384 nightly
The price is $438
$438 total
Sep 2 - Sep 3
Total with taxes and fees
8.8 out of 10, Excellent, (634 reviews)
8.8/10
Excellent
(634 reviews)
"There is no where to sit outside at night unless you have a room with a balcony. I had a room that faced the street and is next to the elevator so it was noisy."
$347 nightly
The price is $396
$396 total
Sep 2 - Sep 3
Total with taxes and fees
Cliffside Resort Condominiums
Cliffside Resort Condominiums3.0 star property
3.2 mi from Town of Southold Town
9.0 out of 10, Wonderful, (278 reviews)
9.0/10
Wonderful
(278 reviews)
"Great place!"
$452 nightly
The price is $516
$516 total
Aug 3 - Aug 4
Total with taxes and fees
9.0 out of 10, Wonderful, (203 reviews)
9.0/10
Wonderful
(203 reviews)
"The hotel doesn’t reception doesn’t open till 9am. For early risers we had to leave the hotel just to get coffee. 9am is unheard of for a hotel"
$394 nightly
The price is $450
$450 total
Aug 3 - Aug 4
Total with taxes and fees
9.6 out of 10, Exceptional, (186 reviews)
9.6/10
Exceptional
(186 reviews)
$593 nightly
The price is $672
$672 total
Sep 2 - Sep 3
Total with taxes and fees
9.2 out of 10, Wonderful, (284 reviews)
9.2/10
Wonderful
(284 reviews)
"Staff looked tired,"
$531 nightly
The price is $607
$607 total
Sep 1 - Sep 2
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.
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.