Southold Packages (Flight + Hotel)

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Top hotels in Southold

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is ฿7,814 per night from 26 May to 27 May
฿7,814
฿9,734 total
26 May - 27 May
includes taxes & fees
9.4/10 Exceptional! (269 reviews)
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

The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
The price is ฿11,636 per night from 13 May to 14 May
฿11,636
฿13,294 total
13 May - 14 May
includes taxes & fees
9.8/10 Exceptional! (16 reviews)
Location was perfect for visiting the wineries… breakfast was to die for!

Reviewed on 22 Mar 2026

Vine & Sand
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is ฿5,121 per night from 17 May to 18 May
฿5,121
฿5,851 total
17 May - 18 May
includes taxes & fees
9.6/10 Exceptional! (496 reviews)
Great for dogs - huge fenced yard

Reviewed on 11 May 2026

The Bentley Hotel Southampton
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.

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