Southold Holiday Packages

Save when you book Southold package deals

Choose two or more items and save on your trip:

Top Southold hotels

The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The Shoals Suites and Slips: Winery hotel with free WiFi and a bar/lounge. Located near the bay.
"Had a beautiful stay MDW! Front desk was so helpful and attentive. Would definitely go back."

Reviewed on 31 May 2025

Get rates
The Shoals Suites and Slips
Baron's Cove

Baron's Cove

4 out of 5
31 West Water Street, Sag Harbor, NY
Baron's Cove: Hotel with free WiFi and free valet parking. Guests love the helpful staff!
"Great location in the heart of town Walk to everything Amazing breakfast too"

Reviewed on 11 Jun. 2025

Get rates
Baron's Cove
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
Pier Blue Inn Old Saybrook - Essex: Pet-friendly hotel with free WiFi and free parking. Located in the historical district.
"Our check in was friendly and quick. VJ was pleasant and interested. There are many dining options nearby. Lovely, family owned and operated."

Reviewed on 9 Jun. 2025

Get rates
Pier Blue Inn Old Saybrook - Essex
Don't see what you're looking for?
See all available properties in Southold
View all properties
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.