Southold Holiday Packages
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Top Southold hotels
Vine & Sand
47100 New York 25 Southold NY
The price is AU$678 per night from 28 May to 29 May
AU$678
28 May - 29 May
includes taxes & fees
Vine & Sand: Business-friendly bed & breakfast with free breakfast and free WiFi.
"Location was perfect for visiting the wineries… breakfast was to die for!"
Reviewed on 22 Mar 2026
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is AU$383 per night from 25 May to 26 May
AU$383
25 May - 26 May
includes taxes & fees
The Shoals Suites and Slips: Winery hotel with free WiFi and a bar/lounge. Located near the bay.
"Very helpful staff. Room was very roomy (no pun intented) and appeared to be recently upgraded. Chit provided for continental breakfast at a local coffee shop that was very good. Definitely recommend."
Reviewed on 5 May 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is AU$141 per night from 7 June to 8 June
AU$141
7 June - 8 June
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex: Pet-friendly hotel with free WiFi and free parking. Located in the historical district.
"Comfortable for a nights stay. Close to nice restaurants and shopping."
Reviewed on 21 May 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.
