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 price is AU$457 per night from 20 Apr to 21 Apr
AU$457
includes taxes & fees
20 Apr - 21 Apr
The Shoals Suites and Slips: Winery hotel with free WiFi and a bar/lounge. Located near the bay.
"Fantastic. The room was very comfortable with a kitchen area and large bathroom. There are boat slips outside and a view of the water."

Reviewed on 14 Apr. 2025

The Shoals Suites and Slips
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$332 per night from 6 May to 7 May
AU$332
includes taxes & fees
6 May - 7 May
Water's Edge Resort & Spa: Business-friendly resort with free WiFi and free valet parking. Located on the waterfront.
"Staff is always very receptive and cordial!"

Reviewed on 10 Apr. 2025

Water's Edge Resort & Spa
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$143 per night from 18 Apr to 19 Apr
AU$143
includes taxes & fees
18 Apr - 19 Apr
Pier Blue Inn Old Saybrook - Essex: Pet-friendly hotel with free WiFi and free parking. Located in the historical district.
"exactly what we expected ... clean and comfortable and would go back ..."

Reviewed on 15 Apr. 2025

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.