Southold Holiday Packages

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Top Southold holiday packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn New York/Central Park South-Midtown West
Hotel Riu Plaza New York Times Square
The Lombardy Hotel
PUBLIC, an Ian Schrager hotel
The Michelangelo Hotel

Top Southold hotels

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is AU$412 per night from 26 Oct to 27 Oct
AU$412
26 Oct - 27 Oct
includes taxes & fees
The Shoals Suites and Slips: Winery hotel with free WiFi and a bar/lounge. Located near the bay.
"It was amazing"

Reviewed on 10 Oct 2025

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 refundableReserve now, pay when you stay
The price is AU$141 per night from 15 Oct to 16 Oct
AU$141
15 Oct - 16 Oct
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex: Pet-friendly hotel with free WiFi and free parking. Located in a shopping district.
"We had a quick stop in the area and picked this hotel. We weee pleasantly surprised! It’s rare to find a small private hotel maintained like a corporate hotel. This is a good one."

Reviewed on 13 Oct 2025

Opens in a new windowPier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$165 per night from 2 Nov to 3 Nov
AU$165
2 Nov - 3 Nov
includes taxes & fees
Quality Inn Old Saybrook - Westbrook: Business-friendly hotel with free breakfast and free WiFi. Located near a metro station.
"Overall, a nice hotel for a one day trip! :)"

Reviewed on 5 Oct 2025

Opens in a new windowQuality Inn Old Saybrook - Westbrook
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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.