Southold Holiday Packages

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Top Southold hotels

Vine & Sand

Vine & Sand

3 out of 5
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

Opens in a new windowVine & Sand
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
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

Opens in a new windowThe Shoals Suites and Slips
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
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

Opens in a new windowPier Blue Inn Old Saybrook - Essex
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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.